Fall in Chicago is the best time of year for architecture lovers. The season brings top events like the annual Pullman House Tour, the Chicago Architecture Biennial — and Open House Chicago, one of the largest architecture festivals in the world.

Each October, this free public event offers behind-the-scenes access to some of Chicago’s most unique buildings. This year, attendees can explore more than 200 sites all around the city on Saturday, Oct. 17 and Sunday, Oct. 18.

With no shortage of places to explore, here are some of the most interesting, historic, and classic Chicago sites you can visit this year to help plan your itinerary.

New sites

Check out these sites around the city that are participating in Open House Chicago for the first time this year.

Smashed Plastic Record Pressing

Housed in a former organ factory, Smashed Plastic is a full-service custom record pressing plant. Get a full demo in the pressing room, then hear the results for yourself in the listening room.

Neighborhood: Hermosa
Dates: Open Saturday and Sunday
More information about Smashed Plastic

Blackhawks Ice Center

Welcome to the official training home of the legendary Chicago Blackhawks. This newly renovated practice facility recently doubled in size to include four ice rinks for practices, tournaments, public skating, and special events.

Neighborhood: Near West Side
Dates: Open Saturday and Sunday
More information about the Blackhawks Ice Center

Farm Zero

This innovative rooftop garden is a first-of-its-kind vertical hydroponic farm, located on the 18th floor of a downtown skyscraper. Guests can take a guided tour, watch harvesting in progress, and even try some samples.

Neighborhood: Loop
Dates: Open Sunday
More information about Farm Zero

Muddy Waters MOJO Museum

Regarded as the “Father of Chicago Blues,” Muddy Waters is one of the city’s most legendary musicians. His former home has been restored and transformed into a museum, with exhibits, a recording studio, outdoor space, live musical performances, and more.

Neighborhood: Bronzeville
Dates: Open Saturday and Sunday
More information about Muddy Waters MOJO Museum

Sears Sunken Garden

Before the Sears Tower became one of the tallest buildings in the world, the original Sears headquarters was located in Chicago’s North Lawndale neighborhood. The site includes a unique sunken garden, a National Landmark that will be open for self-guided or guided tours.

Neighborhood: North Lawndale
Dates: Open Saturday and Sunday
More information about Sears Sunken Garden

TimeLine Theatre

A local theatre company founded in 1997, TimeLine Theatre has proudly celebrated the opening of its new $46 million permanent home. The space includes a 250-seat theatre, gallery space, a cafe/bar, rehearsal space, and more.

Neighborhood: Uptown
Dates: Open Saturday and Sunday
More information about TimeLine Theatre

Cadillac Palace Theatre

One of Chicago’s most stunning spaces, the interior of the Cadillac Palace was inspired by the French palaces of Fontainebleau and Versailles. Admire the ornate lobby and get a close-up stage view from the orchestra level seating.

Neighborhood: Loop
Dates: Open Saturday
More information about Cadillac Palace Theatre 

BandWith Chicago

This Chicago-based non-profit provides access to performing arts programs for underserved communities. Tour the entire building, including the coffee shop, music library, rehearsal spaces, and recording studio.

Neighborhood: Garfield Park
Dates: Open Saturday and Sunday
More information about BandWith

Returning sites

Some of Open House’s greatest hits return this year after a break. Here are just a few to check out.

Avalon Regal Theater

Originally opened in 1927, this stunning theater hosted Barack Obama’s election night victory party in 2008. A full restoration is underway to reopen the building by 2027 in time for its 100th anniversary. Get a rare peek at the grand lobby and auditorium.

Neighborhood: South Shore
Dates: Open Saturday and Sunday
More information about Avalon Regal Theater

Auditorium Theater

This magnificent space was called the “eighth wonder of the world” upon its completion in 1889, heralded for its gilded interior and perfect acoustics. Guests are invited to explore the Auditorium across all six floors.

Neighborhood: Loop
Dates: Open Saturday and Sunday
More information about Auditorium Theatre

Chicago Magic Lounge

Find the hidden entrance inside the laundromat to reveal one of Chicago’s premier magic venues. Tour the Art Deco space with a guide who will explain the club’s many artifacts and ephemera.

Neighborhood: Andersonville
Dates: Open Saturday
More information about Chicago Magic Lounge 

Chicago Board of Trade

One of the city’s most well-known buildings, the Chicago Board of Trade is an imposing Art Deco tower in the heart of the financial district. Visitors can explore the first-floor lobby, on-site museum, and the basement vault.

Neighborhood: Loop
Dates: Open Saturday and Sunday
More information about the Board of Trade

Walt Disney House and Birthplace

Did you know that Walt Disney was born in Chicago? Walt’s parents, Elias and Flora, designed and built this Hermosa home in 1893. The family lived there until 1906 before moving to Missouri. Visitors will be able to take self-guided tours through the home, then visit the gift garage.

Neighborhood: Hermosa
Dates: Open Saturday and Sunday
More information about Walt Disney Birthplace

The Forum

This historic performance space played a central role in Bronzeville’s heyday, hosting everyone from Nat King Cole to the Jackson 5. Visitors can tour the iconic hall as it moves towards rehabilitation, while enjoying a full program of live musical performances.

Neighborhood: Bronzeville
Dates: Open Saturday and Sunday
More information about The Forum

Park Castle Condominiums

Open House offers a rare opportunity to explore one of Chicago’s most unique residential buildings, designed in 1925 to look like a castle. Visitors are invited to wander the front courtyards and the extravagant indoor pool.

Neighborhood: Rogers Park
Dates: Open Saturday and Sunday
More information about Park Castle Condominiums 

The Plant

A former meatpacking facility, this dynamic space is now a sustainable incubator for small food businesses. View food production spaces not open to the public, explore the museum, and purchase food and drink made on site.

Neighborhood: Back of the Yards
Dates: Open Saturday and Sunday
More information about The Plant

Explore more: See all Open House Chicago 2026 sites and start planning your itinerary.

Chicago is a city renowned for its rich cultural diversity, and there’s no better time to experience it than during National Hispanic Heritage Month.

From Sept. 15 to Oct. 15, the city comes alive with celebrations that honor the contributions of the Hispanic and Latine communities. Whether you’re a lifelong Chicagoan or a first-time visitor, there are countless ways to immerse yourself in Chicago’s vibrant Hispanic culture this month and all year long.

Mexican Independence Day events

Kick off Hispanic Heritage Month with Mexican Independence Day celebrations throughout the city.

El Grito in Grant Park
Saturday, Sept. 12 and Sunday, Sept. 13, 2026
This outdoor festival features music from local and international artists, authentic Mexican food, a mercadito of artisans, a special kid-friendly area, fireworks, and more throughout the weekend.

Little Village Mexican Independence Day Parade
Sunday, Sept. 13, 2026
The neighborhood’s 55th annual Mexican Independence Day Parade is one of the month’s standout events. The parade honors the resilience and cultural richness of the Mexican community, with performances, dancers, horseback riders, and more.

Explore more: Find more Mexican Independence Day events throughout the city.

Hispanic heritage celebrations and events in Chicago

Chicago’s sports teams, cultural institutions, and outdoor spaces are all honoring National Hispanic Heritage Month 2026 in Chicago this year.

Chicago Fire Hispanic Heritage Night at Soldier Field
Sunday, Sept. 13, 2026
Cheer on the Chicago Fire as they honor Hispanic Heritage with a special evening celebration, featuring local performing arts groups.

Chicago Cubs Hispanic Heritage Celebration at Wrigley Field
Tuesday, Sept. 15, 2026
Snag a special limited-edition Cubs heritage jersey. A portion of the proceeds from sales of the special ticket offer will go to non-profit La Casa Norte.

White Sox Hispanic Heritage Night Celebration at Rate Field
Friday, Sept. 25, 2026
Purchase a special ticket package and get a commemorative t-shirt. Plus, play loteria with other fans in the ballpark before the game.

Hispanic Heritage Fest at Brookfield Zoo
Saturday, Sept. 26, 2026
Included in your zoo admission, this free event will include live music, cultural performances, and experiences for all ages.

Latine History Events at Chicago Public Libraries
Sept. 15 – Oct. 15, 2026
The city’s public libraries will be hosting a diverse array of free events, including bilingual story times, film screenings, crafts, book discussions, and more.

Hispanic Heritage Month in Chicago parks
Sept. 15 – Oct. 15, 2026
The Chicago Park District is offering a variety of free events in parks across Chicago, including dance performances, live music, and family-friendly activities.

Latine Heritage Month at the Chicago History Museum
Saturday, Oct. 3, 2026
This commemorative event will honor Chicago’s Latino/a/e populations with a day of learning, interactive activities, and community connection.

Museum exhibits and cultural happenings

Here are just a few of the upcoming events, performances, and happenings honoring Hispanic culture this month.

Destinos Chicago International Latino Theater Festival
Sept. 14 – Oct. 11, 2026
The 9th annual Destinos Theater Festival showcases Latino theatre companies from Chicago and across the country. Explore more than a dozen unique shows at venues around the city.

Where Memory Lives: 40 Years of Día de Muertos
Sept. 25 – Nov. 29, 2026
The National Museum of Mexican Art hosts the 40th annual version of this beloved exhibition, tracing the evolution of Day of the Dead and the museum itself.

Chicago Latino Dance Festival
Sept. 29 – Oct. 11, 2026
This free, annual event is a celebration of the rich diversity of Latino dance and cultural traditions. This fourth edition of the festival will feature 20 performing groups across multiple venues.

Walking Tours with the Chicago History Museum
Multiple dates in September and October
The Chicago History Museum hosts these expert-led walking tours, featuring two culturally rich Chicago neighborhoods: public art and murals in Pilsen, and Puerto Rican culture in Humboldt Park.

Latinx Heritage Month at the Field Museum
Sept. 15 – Oct. 15, 2026
The Field Museum celebrates Hispanic heritage with a family-friendly story time, career fair, curator talks, and more.

Hispanic-owned restaurants in Chicago

There’s no better time to enjoy the rich and diverse culinary offerings of Chicago’s Hispanic-owned restaurants.

• Diego: This award-winning West Town restaurant specializes in Baja-Mediterranean street food and agave cocktails.
• Irazu: A local go-to for Costa Rican cuisine, Irazu has been serving up delicious cuisine and “pura vida” vibes since 1990.
• Istmo Oaxacan Cuisine: A refined Lakeview spot that explores the rich culinary traditions of Mexico’s Oaxaca region.
• Little Madrid Tapas Cafe: Get transported to Spain at this authentic Andersonville spot, serving paella, croquettes, sangria, and more.
• La Licor Panamericana: At La Licor, dishes combine culinary ideas from across Latin American cultures for a unique fusion of flavors.
• Matilda: This chic Mexican-Peruvian spot in River North is already getting buzz for its sleek decor and artful plates.
• Marina’s Bistro and Rum Bar: In Uptown, Marina’s offers a taste of the Caribbean with its flavorful island-inspired dishes and rum-based cocktails.
• El Nuevo Mexicano: This family-owned restaurant offers a menu full of authentic dishes and a welcoming atmosphere.
• Tanta Chicago: A rooftop restaurant in River North, Tanta brings the vibrant flavors of Peru to Chicago with ceviche, pisco sours, and more classic options.

Keep exploring Hispanic and Latino culture in Chicago.

Want to know what’s happening this weekend in Chicago? Look no further. There’s a whole calendar of exciting events, exhibits, and activities taking place all over the city this month in Chicago.

A few of this weekends highlights include:

• Mexican Independence Day celebrations around the city
• One of the Chicago Cubs last homestands of the regular season
• Top neighborhoods events like the Printers Row Lit Fest and the Ravenswood Art Walk 

Check out just a few of the events and happening in Chicago this weekend, Sept. 11 – 13.

Sept. 12 – 13

El Grito Chicago

El Grito Chicago returns to Grant Park's Butler Field September 12–13, 2026, for a two-day celebration of Mexican culture, music, food, and pride in the…

South Loop

Event details

Saturday, Sept. 12 – Sunday, Sept. 13

Grant Park
337 E Randolph St

Sep 13

26th Street Mexican Independence Day Parade

One of the largest parades in the Midwest, the annual 26th Street Mexican Independence Day Parade draws thousands of participants and spectators to the heart of Little Village.

Event details

Sunday September 13, 2026

Little Village
26th Street and Albany Avenue to Kostner Avenue.

Sep 13

Midway 5K

Runners and walkers will get the rare opportunity to take over the airfield at Midway International Airport for a family-friendly race day like no other. There will be a 5K run, a 5K walk, and a mile event for kids.

Event details

Sunday September 13, 2026

Midway International Airport

Sept. 11 – 13

German American Oktoberfest

Oktoberfest comes to the heart of Lincoln Square, a neighborhood with deep German roots. This free street festival brings German food, beer, traditional music, folk dancing, and plenty of old-world charm.

Friday September 11, 2026 — Sunday September 13, 2026

Sep 12

Chicago Football Classic

The Chicago Football Classic returns to Soldier Field, with Mississippi Valley State University taking on Lincoln University. There will also be a career fair connecting students with historically Black colleges and universities.

Event details

Saturday September 12, 2026

Soldier Field

Sept. 12 – 13

Printers Row Lit Fest

Now in its 41st year,  the Printers Row Lit Fest on Saturday, September 12 and Sunday, September 13, from 10am to 6pm, is the largest…

Event details

Saturday, Sept. 12 – Sunday, Sept. 13

637 South Dearborn St., Chicago, IL.
637 South Dearborn St., Chicago, IL.

Sept. 12 – 13

Ravenswood ArtWalk Tour of Arts & Industry

The Ravenswood ArtWalk (RAW) Tour of Arts and Industry is a weekend-long celebration of our local creative community. Stretching from Lawrence south to Irving Park along Ravenswood…

Event details

Saturday, Sept. 12 – Sunday, Sept. 13

Ravenswood Industrial Corridor
4191 N Ravenswood Ave

Sept. 12 – 13

Renegade Craft Fair

Shop more than 400 independent makers, artists, and designers from Chicago and beyond. Browse a thoughtfully curated selection of handmade goods spanning jewelry, clothing, ceramics, and art prints.

Event details

Saturday September 12, 2026 — Sunday September 13, 2026

Division Street in Wicker Park

Sep 12

Wicker Park Fine Art Fair

The much-loved triangle of public land known as Wicker Park, the neighborhood’s namesake, will be the site of the second annual Wicker Park Fine Art…

Wicker Park / Bucktown

Event details

Saturday September 12, 2026

Wicker Park
1425 N. Damen Ave

Sep 12

Grand Welcoming & Community Marketplace

Join The Renaissance Collaborative (TRC) on Saturday, September 12, as we reopen the doors of the Historic Former Wabash YMCA to the Bronzeville community and…

Event details

Saturday September 12, 2026

Historic Former Wabash YMCA
3763 S Wabash Avenue

Sept. 11 – 13

Chicago Cubs vs. Pittsburgh Pirates

Come cheer on the Cubs!

Wrigleyville

Event details

Friday, Sept. 11 – Sunday, Sept. 13

Wrigley Field
1060 W. Addison St., Chicago, IL

Sept. 13

Maxwell Street

Visitors to Maxwell Street will experience an eclectic mix of foods and finds—including handmade crafts, resale housewares, clothing, and much more.

Event details

Sunday September 13, 2026

Maxwell Street
Halsted & Maxwell

Sep 12

Chief Keef Live 2026

Chief Keef will kick off his newly announced 19-date nationwide headlining tour with a massive hometown performance in Chicago, Illinois, on Saturday, September 12, 2026.

South Loop

Event details

Saturday September 12, 2026

Huntington Bank Pavilion at Northerly Island
1300 S. Linn White Dr.

Sept. 11 – 13

Jekyll& Hyde

Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…

Event details

Sept. 8 – Nov. 8, 2026

Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611

Sept. 11 – 13

Tangible Sound: Arrival to a Higher Ground

Imagine walking inside the thunderous sound of a taiko drum or feeling enveloped by the sinuous sounds of a saxophone, cello, or bass. What if…

Loop

Event details

June 29 – Sept. 27, 2026

Chicago Cultural Center
78 E Washington St

Explore our events calendar for more Chicago events and happenings.

Please note that all events are subject to change.

Chicago is a city with history — a whole lot of history, dating back to before the city’s founding in 1837. So it’s hardly surprising that it’s also a city with ghosts — a whole lot of ghosts.

These alleged hauntings stem from some of the city’s darkest chapters, like the Great Chicago Fire, the sinking of the SS Eastland, and when a serial killer lured victims from the Chicago World’s Fair.

Check out some of the spine-chilling tales that highlight Chicago’s haunted history — even skeptics will be fascinated.

Death alley in the Theatre District

In 1903, Chicago’s Iroquois Theatre was the site of an infamous fire.

Located in the city’s Theatre District, the newly built building claimed to be fireproof. But during its inaugural performance, a blaze broke out. When patrons tried to escape, they found many of the exits were blocked.

After the flames subsided, around 600 people were pronounced dead. As bodies were recovered from the scene, the alley behind the theatre functioned as a temporary morgue.

Today, the site is home to James M. Nederlander Theatre. The alleyway behind the theatre, now known as “Death Alley”, still exists today. There have been reports of faint cries, apparitions, and feelings of being touched or even pushed by invisible entities.

Ghostly tales don’t seem to keep avid theatre-goers away, however. The Nederlander Theatre’s stunning architecture and run of premieres and Broadway shows keep the crowds coming and the ghosts at bay.

H.H. Holmes’ Murder Castle

Made famous by the blockbuster book The Devil in the White City, the country’s first serial killer is forever linked with the Chicago World’s Fair of 1893.

It’s hard to know definitively just how many people Holmes murdered. While he confessed to 27, most of whom were women lured from the nearby World’s Fair, some historians believe the number to be much higher.

One of the infamous sites associated with Holmes is the location of his notorious “Murder Castle” in Chicago’s Englewood neighborhood.

When constructing the building, Holmes hired multiple contractors to ensure that no one person, aside from himself, knew the floor plan in its entirety. The bizarre blueprint included stairs that led to nowhere, oddly angled hallways and windowless rooms, designed to disorient and trap his victims.

While the building has been replaced by a post office, maintenance workers report odd sightings and feelings of intense anxiety while in the new building’s basement.

You can learn more about H. H. Holmes and the World’s Fair on local tours like The Devil in the White City Bus Tour.

Lincoln Park

The city’s largest green space, Lincoln Park is a lakefront oasis that’s popular with locals and visitors alike. But the park may be concealing a dark secret underground.

The southern edge of the park originally served as a massive city cemetery throughout the mid-1800s. During the Great Chicago Fire, all the wooden grave markers were destroyed — and their locations became lost to history.

One remnant of this macabre past is the limestone Couch Tomb, which still stands at the south end of Lincoln Park.

In 1998, construction workers digging in the park discovered human bones. In total, experts unearthed the skeletal remains of more than 80 people, including one 19th-century iron coffin.

Today, it’s estimate that thousands of bodies may remain buried in unmarked grave throughout the park. If you’d like to learn more, the Lincoln Park Zoo offers Haunted History Tours each October.

Congress Plaza Hotel

Known as one the most haunted places in Illinois, the Congress Plaza Hotel’s history begins with the 1893 World’s Fair.

The luxurious hotel was built to help house the influx of visitors to the city during the fair, and quickly became the focus of rumors.

For instance, some say that mobster Al Capone and his cohorts ran their headquarters and even committed gruesome crimes there, although these claims have come under some scrutiny.

Mob rumors aside, if you find yourself spending the night in the South Tower, you might just run into “Peg Leg Johnny,” the spirit of a man who was allegedly murdered in the alley behind the hotel.

The North Tower has its own urban legends. Hotel staff have reported seeing the apparition of a playful young boy on the 12th floor. He is believed to be the spirit of a child who, along with his sibling, was thrown from the North Tower by his mother. She, too, jumped to her death.

The most hauntings, however, take place in the infamous Room 441. Visitors have reported seeing the silhouette of a woman, objects moving around the room, or lights turning on and off at random. The room is even believed to be the inspiration for Stephen King’s horror story, 1408, about a haunted hotel room.

Explore more: Learn the chilling stories behind Chicago’s most historic — and haunted — hotels.

Site of the Eastland Disaster, Chicago River

Chicago suffered one of its most devastating tragedies on July 25, 1915, when the SS Eastland steamship capsized in the Chicago River, trapping 2,573 passengers on board.

The disaster occurred shortly after the Titanic sinking, when the lack of lifeboats on passenger ships came under scrutiny. A new regulation was passed to ensure enough safety vessels on ships.

Unfortunately, the addition of these lifeboats in the Eastland’s case caused the already top-heavy ship to roll over in the Chicago River. In total, 844 passengers and crew members died that day.

Various Chicago establishments were used as makeshift morgues to store the recovered bodies. Many of these spots have experienced ghostly sightings, and are said to elicit feelings of general unease among visitors.

Reports of apparitions and unusual wave patterns also extend to the stretch of river where the Eastland disaster occurred between Clark and LaSalle Streets. Many of the victims are buried in the Bohemian National Cemetery on the city’s North Side.

The Drake Hotel

The Congress Plaza isn’t the only hotel in Chicago with a ghostly history.

Built in 1920, The Drake has long epitomized elegance and opulence, with illustrious guests such as Bing Crosby, Frank Sinatra, Dean Martin, Marilyn Monroe, Queen Elizabeth II, Winston Churchill, Princess Diana — and a few forlorn ghosts.

Legend has it that the hotel is haunted by two famous women — The Woman in Black and the Woman in Red.

The Woman in Black was a killer who shot a Chicago socialite inside her eight-floor suite at The Drake in 1944, but was never identified or apprehended. Today, a mysterious woman, dressed in black, is sometimes spotted on the hotel’s eighth floor.

The story of the Woman in Red starts at the hotel’s New Year’s Eve gala in 1920. One of the partygoers discovered her philandering husband (or fiancé, depending on who’s telling the story). In a frenzy of jealousy and rage, she takes an elevator to the 10th floor, and swiftly jumps to her death. Her ghostly apparition can be seen haunting the hotel’s ballrooms and the 10th floor.

See if you can spot any spirits during high tea at the Palm Court or, better still, book a stay at this historic hotel.

Graceland Cemetery

Built in 1860, Graceland Cemetery is the final resting place of some of Chicago’s most notable individuals, like David Adler, John Kinzie, Potter Palmer, George Pullman, Marshall Field, and more.

However, it isn’t an illustrious personage that causes a stir at the cemetery. Rather, it’s a 6-year-old girl by the name of Inez Clarke.

The story goes that Inez was struck by lightning in 1880 while playing in the rain. Her parents memorialized her with a stone likeness on her grave. They added a glass box to symbolically protect their daughter from the elements that had so tragically taken her.

On stormy days, cemetery workers and visitors have reported the statue entirely missing. As soon as the storm subsides, however, the statue of Inez Clarke returns to its glass box. Many surmise that she leaves to once again play in the rain.

Site of the St. Valentine’s Day Massacre

In 1929, four unknown assailants opened fire on a Lincoln Park garage where members of a North Side gang had gathered. Seven people were killed and the nation was shocked at the brutal crime.

While the killings technically remain unsolved, there’s little doubt as to who was actually behind them — Al Capone. The famous gangster was in a brutal gang war with the North Side gang leader Bugs Moran, who managed to escape the hit. But for the rest of his days, Capone would claim that he was haunted by Jimmy Clark, one of the men killed in the Valentine’s Day Massacre.

Today, the garage has been demolished and nothing physical remains on the site of the massacre — though many claim that something supernatural remains. And you can still visit Chicago Pizza and Oven Grinder, situated directly across the street from the murder site. The brownstone that houses the restaurant is said to be the lookout spot used by Capone’s assassins.

Jane Addams Hull House

The famed Hull House was a communal residence on Chicago’s West Side, run by Jane Addams, aka “the mother of social work,” to assist recently arrived immigrants.

It was Addams, in fact, who first spoke of the property’s paranormal nature when she claimed footsteps could be heard in the room where she slept. She assumed this was the wife of Charles Hull, the original owner of the building, who had passed away in that room.

The most famous urban legend of Hull House, however, is the tale of the “Devil Baby.” The story goes that a mother-to-be and devout Catholic hung a picture of the Virgin Mary in her home in order to bless her impending motherhood. Her husband, however, was just as devout an atheist, and angrily ripped the picture from the wall declaring, “I’d rather have the Devil in the house!”

The child was reportedly born with scaly skin, hooves, and horns, and summarily abandoned at Hull House. Accounts claim that Addams tried to baptize the baby, but could not, eventually locking him in the attic until his death.

Although this story is a folktale and has no basis in fact, it still captivates those who visit Hull House. And in October, the museum hosts The Haunting of Hull-House tours that tell the story of the Devil Baby and more spooky sightings.

Chicago’s summer festival season may be winding down, but there’s still another standout event on the city’s cultural calendar — Chicago Live Festival at Navy Pier.

The Midwest’s largest free performing arts festival is set to take over the lakefront on Saturday, Sept. 19 and Sunday, Sept. 20, 2026.

The annual event is designed to showcase the city’s world-class cultural scene, with free performances from more than 100 artists and organizations.

Check out this year’s performances and start planning your visit to Chicago Live Festival.

When is the Chicago Live Festival?

The festival will take place on Saturday, Sept. 19 and Sunday, Sept. 20.

Check back for the full daily schedule of performances.

What is the Chicago Live Festival?

Back for its sixth year, the Chicago Live Festival will feature more than 100 local groups from Chicago and beyond.

Fest-goers can expect two full days of back-to-back performances across multiple lakefront stages — all surrounded by the stunning skyline views you can only find at iconic Navy Pier.

The multi-disciplinary festival is a vibrant representation of the city’s rich and diverse artistic spirit. The packed lineup includes a huge variety of Chicago-grown talent, including dance troupes, orchestras, theatre companies, improv troupes, DJs, and more.

Performances will unfold across the Pier, ensuring non-stop entertainment all weekend long. Even better, all events and performances are free and open to the public.

Chicago Live was founded in 2021 to reconnect audiences with Chicago’s performing arts community. The festival has continued to grow, making it a true testament to the resilience of Chicago’s performing arts community.

What is the Chicago Live Festival 2026 lineup?

The full Chicago Live Festival lineup represents the depth and diversity of Chicago’s performing arts scene, spanning genres and encompassing both emerging talents and established stars.

A few of the most-anticipated acts at this year’s festival include:

• Common, the Emmy, Grammy, and Academy Award-winning artist
• Joffrey Ballet
• The Second City
• Anthony Rapp
• Hubbard Street Dance Chicago
• Melody Angel
• Trinity Irish Dancers

Nearly one-third of this year’s lineup will be performing at the fest for the first time, including:

• RuPaul’s Drag Race stars Utica and Denali
• Q Brothers
• Nico Segal
• Fat Theatre Project

Check out all the groups and artists performing at the Chicago Live Festival this year:

Check back soon for the full 2026 schedule for Chicago Live!

In the meantime, start planning your visit to Navy Pier.

Chicago’s fall events calendar is overflowing with cultural happenings — including music, theatre, film, visual arts, and everything in between.

If you’re looking for things to do this fall in Chicago, mark your calendar for these exciting arts and culture events. From immersive arts experiences to genre-defying film festivals, there’s truly something for everyone to enjoy.

Explore our list of can’t-miss events, grab your tickets, and start looking forward to your jam-packed fall season in Chicago.

Art and culture events

Chicago Exhibition Week

Sept. 14 – 20, 2026
Chicago Exhibition Week is back and bigger than ever. More than 50 galleries and creative spaces will host exhibits, tours, performances, and more during this weeklong celebration of the city’s arts scene.

Chicago Live Festival

Sept. 19 – 20, 2026
The Midwest’s largest free performing arts festival, Chicago Live Festival at Navy Pier brings a diverse lineup of dance, music, and theatre performances from local and national artists and groups.

Chicago Fashion Week

Oct. 8 – 18, 2026
Back for its third year, Chicago Fashion Week celebrates every aspect of the city’s design ecosystem. Find runway shows, in-store events, pop-up markets, and more.

Arts in the Dark

Oct. 24, 2026
Arts in the Dark celebrates Halloween as the artists’ holiday with a mesmerizing evening parade. Join thousands of spectators in downtown Chicago as they admire the enchanting procession of puppets, giant lanterns, floats, and performers.

312 Comedy Festival

Nov. 5 – 15, 2026
312 Comedy Festival is a multi-day celebration of stand-up comedy that features performances from more than 20 top comedians across six Chicago venues.

Chicago Humanities Festival

Sept. 14 – Nov. 14, 2026
The fall iteration of the Chicago Humanities Festival will include nearly 50 events, featuring luminaries from a range of fields. Hear from famous actors, comedians, photographers, intellectuals, Pulitzer Prize-winning authors, and more.

Fall theatre guide

Catch Broadway hits, original productions, and more on stages across Chicago this fall. Get your tickets today.

Find upcoming shows

Architecture events

Historic Pullman House Tour

Oct. 10 – 11, 2026
Now in its 53rd year, Historic Pullman House Tour lets guests step inside private homes surrounding Chicago’s only National Park. Admire historic residential architecture, from workers’ cottages to stately mansions.

Open House Chicago

Oct. 17 – 18, 2026
Open House Chicago is one of the world’s largest architecture festivals. This free citywide event lets you go behind the scenes at hundreds of buildings around Chicago, including skyscrapers, historic landmarks, religious buildings, private clubs, and more.

Film festivals

Chicago International Film Festival

Oct. 14 – 25, 2026
Chicago International Film Festival is North America’s longest-running competitive film festival. The prestigious event brings 12 days of screenings to venues around the city, plus special events and appearances by directors and talent.

Reeling Film Festival

Sept. 17 – 27, 2026
The second-oldest LGBTQ+ film festival in the country, Reeling Film Festival features a diverse selection of works that explore different aspects of queer culture, history, and daily life.

Chicago Underground Film Festival

Sept. 23 – 27, 2026
The longest-running event of its kind, Chicago Underground Film Festival highlights genre-defying works from independent artists. This year brings an exciting array of experimental films, documentaries, and world premieres.

Black Harvest Film Festival

Nov. 6 – 15, 2026
Celebrate Black storytelling in cinema during the 32nd annual Black Harvest Film Festival, spotlighting rising voices and acclaimed filmmakers at the Gene Siskel Film Center.

Live music

Englewood Jazz Festival

Sept. 17 – 19, 2026
Now in its 27th year, Englewood Jazz Festival offers three days of live music with a strong emphasis on homegrown artists and the neighborhood’s rich jazz legacy.

Riot Fest & Carnival

Sept. 18 – 20, 2026
Riot Fest & Carnival, Chicago’s premier punk rock festival, takes over Douglass Park with old-school rides, fun eats, and modern and throwback acts. Headliners include Tool, Twenty One Pilots, Pierce the Veil, and more.

World Music Festival

Sept. 25 – Oct. 4, 2026
Experience rhythms from around the globe at Chicago’s World Music Festival, a multi-venue celebration spotlighting international artists and genres. All performances are free and open to the public.

Hyde Park Jazz Festival

Sept. 26 – 27, 2026
Every fall, the free Hyde Park Jazz Festival celebrates the roots of Chicago-style jazz with diverse artist lineups on outdoor and indoor stages throughout Hyde Park.

Chicago Made Music Showcase

Oct. 24, 2026
Local creatives will perform before a live audience and panel of industry professionals during the Chicago Made Music Showcase Finale at the Chicago Cultural Center for a chance to win a career-changing grand prize.

Museum exhibits

Mary Cassatt: After Impressionism

Sept. 6 – Jan. 3, 2027
The newest exhibit at the acclaimed Art Institute of Chicago, Mary Cassatt: After Impressionism shines a spotlight on the American artist’s most ambitious and experimental work.

Where Memory Lives: 40 Years of Día de Muertos

Sept. 25 – Nov. 29, 2026
The National Museum of Mexican Art hosts this annual exhibition, celebrating the history and culture of Day of the Dead through the perspective of Mexican artists. Where Memory Lives: 40 Years of Día de Muertos traces the evolution of Day of the Dead and the museum itself.

Anne Frank: The Exhibition

Now open through Jan. 31, 2027
Step inside a meticulous full-scale reconstruction of the Annex where Anne Frank and her family hid for two years during Nazi occupation. Anne Frank: The Exhibition at the Griffin Museum of Science & Industry features never-before-seen artifacts from Anne Frank’s life.

Pokémon Fossil Museum

Now open through April 11, 2027
Pokémon Fossil Museum at the Field Museum blends the world of Pokémon and paleontology. Guests can compare Pokémon fossils to real-life dinosaurs and ancient life forms.

Paris in Black: Internationalism and the Black Renaissance

Now open
Explore the experiences of Black artists in Europe as they sought a refuge for creative expression. The Paris in Black collection explores almost a century of Black art at The DuSable Black History Museum and Education Center.

Food festivals

Chicago Gourmet

Sept. 24 – 27, 2026
Chicago Gourmet is the city’s signature fall food festival, showcasing some of the city’s best chefs and culinary talent. This year, Chicago Gourmet celebrates the vibrant intersection of food and dance.

World Dumpling Fest

Sept. 19 – 20, 2026
Come sample dumplings from around the world, while getting a taste of Chicago’s international dining scene. World Dumpling Fest also features live performances representing Chicago’s cultural communities.

Lincoln Park Wine Fest

Oct. 9 – 11, 2026
Sip wine while strolling an open-air market of sommeliers, food vendors, and live music at Lincoln Park Wine Festival, a local favorite hosted in tranquil Jonquil Park.

Explore more: Check out the full list of fall food festivals in Chicago, from tasting events to Oktoberfest celebrations.

At the lakefront Adler Planetarium, the night sky comes into sharp focus thanks to the largest publicly accessible telescope in Chicago. Through the popular  Scopes at the Adler program, visitors can enjoy free telescope viewing and experience remarkable sights, from sunspots during the day to the moon, planets, and distant stars after sunset. Whether you’re an experienced stargazer or peering through a telescope for the first time, Scopes at the Adler offers a way to connect with the cosmos.

The centerpiece of the program is the Doane Observatory, which houses a 20-inch Clark refractor telescope. As Chicago’s largest telescope, it provides some of the clearest and brightest views of the universe anywhere in the city. Knowledgeable staff and volunteers are on hand to help visitors navigate the night sky, point out celestial highlights visible during sessions, and answer questions.

The Doane Observatory welcomes the public for night observing on Wednesdays, weather permitting, from dusk until 10 p.m. Because opening times depend on sunset, the schedule changes throughout the year. Viewing is available on a first-come, first-served basis, making it easy to stop by and see what’s visible. No museum admission, ticket, or reservation is required.

Every visit to Scopes at the Adler is a little different. The moon’s phases, the changing positions of planets, and seasonal constellations mean there’s always something new to discover. Weather conditions also influence what can be viewed.

Visitors don’t need to wait until dark, though. The Adler recently began offering daytime solar viewing on Mondays, Fridays, and Saturdays from 10 a.m. to 1 p.m., weather permitting. Using specially equipped telescopes, guests can safely observe the sun and its features, including sunspots and solar activity. Additional smaller telescopes are set up on the Telescope Terrace, giving visitors even more opportunities to explore the sky.

As part of Chicago’s lakefront Museum Campus, the Adler Planetarium offers a unique opportunity to discover the wonders of astronomy in an easily accessible setting. And Scopes at the Adler brings the universe a little closer.

Start planning your visit to the Adler Planetarium today.

This month, enjoy live jazz in the heart of downtown, tour a Chicago neighborhood with a friendly local, and browse the city’s longest-running outdoor market — all without spending a dime.

What are some free things to do in Chicago this month?

Chicago is bursting with free things to do this September, including free music festivals like the iconic Chicago Jazz Festival, free admission to top Chicago museums, Labor Day festivities, neighborhood Oktoberfests, and so much more. Start planning your budget trip to Chicago with this round-up of the free things to do and see all month long.

1. Check out free jazz festivals

Multiple dates in September
Chicago is the place to be for jazz fans this September. These free music festivals bring unmatched talent and pay homage to Chicago’s deep jazz roots. Don’t miss out on three weekends full of music with these exciting (and wallet-friendly) fests.

• Chicago Jazz Festival (Sept. 3 – 6): Spend Labor Day weekend checking out some of Chicago’s best jazz performances.
• Englewood Jazz Festival (Sept. 17 – 19): This year’s festival celebrates its 27th anniversary, bringing together next-generation musicians and established jazz icons.
• Hyde Park Jazz Fest (Sept. 26 – 27): The 20th annual Hyde Park Jazz festival presents free jazz shows in addition to food and merchant vendors.

Explore more: Check out more music festivals in Chicago.

2. Immerse yourself in culture at Navy Pier

Sept. 19 – 20, 2026
Mark your calendar for the largest free performing arts festival in the Midwest. The annual Chicago Live! festival will bring more than 100 performing arts organizations and artists to the lakefront for two packed days of performances, all free and open to the public.

The extensive lineup showcases Chicago’s rich cultural scene through live music, dance, theatre, and multidisciplinary performances.

3. Attend the Chicago Labor Day parade and festival

Sept. 5, 2026
In the historic Pullman neighborhood, the annual Chicago Labor Day Parade and Eddie Fest brings the community together to celebrate the city’s influential role in labor history.

The parade will march through the 10th Ward, followed by a free festival in Steelworkers Park with music, food, and family fun.

Explore more: Visit the Pullman National Historical Park to discover the area’s fascinating history.

4. Catch the last free summer fireworks

Sept. 2 and 5, 2026
End your summer on a dazzling note with the free fireworks at Navy Pier.

Locals and visitors gather on the lakefront to enjoy iconic skyline views, dazzling pyrotechnic displays, and a classic summertime Chicago experience. Don’t skip your last chance to see this free show before it ends for the season.

Explore more: Find more things to do at Navy Pier, from rides and games to theatre and immersive experiences.

5. Explore Chicago neighborhoods with a local guide

Sept. 10, 2026
Whether you’re a visitor or a local, there’s always something new to discover in Chicago’s vibrant neighborhoods.

International Greeter Day is the perfect opportunity to explore a new neighborhood, with the help of a friendly local guide. Meet in Millennium Park before embarking on a free walk that will delve into a neighborhood’s history, top attractions, and hidden gems.

International Greeter Day in Chicago is brought to you by Chicago Greeter, which pairs visitors and locals for free neighborhood walks year-round.

6. Attend the World Music Festival

Sept. 25 – Oct. 4, 2026
Music from around the world takes over Chicago during the annual World Music Festival, featuring a diverse array of international artists and groups. This free festival showcases genres from around the globe at iconic venues throughout Chicago, including the Chicago Cultural Center.

7. Enjoy free museum days

Multiple dates in September
Stand on the other side of the glass from a beluga whale, explore the depths of the galaxy, or come face-to-face with the most complete T. rex skeleton ever found. Don’t miss what Chicago’s museums have in store on these upcoming free days for Illinois residents:

• Field Museum is free every Wednesday this year
• Art Institute of Chicago is free every Thursday evening through Sept. 17
• Shedd Aquarium is free every Tuesday evening in September
• Chicago History Museum is free Sept. 7 and 24
• Griffin Museum of Science and Industry is free on Sept. 1, 2, 8 – 10, 15, 16, 20 – 23, and 27 – 30
• Adler Planetarium is free on Sept. 8, 9, 10, 14, 15, and 16
• Museum of Contemporary Art is free every Tuesday evening

Explore more: Mark your calendar for free museum days throughout the year.

8. Shop Chicago’s oldest outdoor market

Sept. 13, 2026
Maxwell Street Market is Chicago’s oldest open-air market, dating all the way back to 1847. This seasonal Sunday marketplace includes food, handmade crafts, housewares, clothing, live entertainment, and more.

The September market will be dedicated to kids and families, with young vendors and kid-friendly entertainment for a fun, family-focused experience.

9. Attend a neighborhood festival

Multiple dates in September
If you can count on one thing in Chicago, it’s the abundance of festivals happening around the city every month. Whether you’re in the mood for music, food, art, or culture, there’s a free event for you.

• German-American Oktoberfest (Sept. 11 – 13): Spend an evening indulging in traditional German food, drinks, and dancing to live bands at this Lincoln Square festival.
• Printers Row Lit Fest (Sept. 12 – 13): The Midwest’s largest free outdoor literary festival features authors, exhibitors, and booksellers in the South Loop.
• Lakeview East Art Festival (Sept. 19 – 20): More than 150 artists showcase their unique artwork, alongside entertainment stages and family activities. There is a $5 suggested donation.

Explore more: Browse our complete list of September festivals and find more things to do.

10. Attend open gallery nights

Sept. 18, 2026
Chicago’s art scene comes to life in our neighborhoods, where local galleries are constantly pushing boundaries and showcasing the latest talent.

Explore the latest and discover up-and-coming artists during these free gallery and open studio nights around Chicago:

• Bronzeville Art District Trolley Tour (Sept. 18): Hop on and off this free trolley that takes art lovers to different galleries throughout the Bronzeville neighborhood.
• 3rd Friday at Bridgeport Art Center (Sept. 18): This vibrant maker space welcomes the public once a month to explore the works of local painters, sculptors, ceramicists, woodworkers, and more.
• 3rd Friday at Zhou B Art Center (Sept. 18): This converted warehouse in the Bridgeport neighborhood has become a leading hub for international and local art.

Looking for more? Check out our guide on free things to do in Chicago all year long.

While summer may be winding down, there’s no shortage of music festivals, art walks, cultural events, and more throughout September in Chicago.

The month kicks off with a long weekend (check out our Labor Day guide) and wraps up with the first days of autumn (find things to do this fall in Chicago). And there’s plenty to do in between, including tons of festivals and events celebrating National Hispanic Heritage Month, food, culture, music, and film.

Check out these top picks for things to do in Chicago throughout September 2026.

Top events in Chicago this September

Chicago Jazz Festival (Sept. 3 – 6): The oldest of Chicago’s free lakefront music festivals, the Chicago Jazz Festival in downtown Millennium Park is a true bucket list event for jazz fans. This year’s lineup features a mix of established stars and rising talent.

Chicago Labor Day Parade and Eddie Fest (Sept. 5): Celebrate the holiday weekend in the historic Pullman neighborhood with a vibrant community parade that culminates in a free family-friendly festival, featuring music, food, drinks, and games in Steelworkers Park.

Bike the Drive (Sept. 6): Now in its 25th year, Bike the Drive invites riders of all ages and experience levels to cruise along iconic Lake Shore Drive, with sweeping views at every turn. The morning wraps up with a post-ride festival in Grant Park.

El Grito Festival (Sept. 12 – 13): Celebrate Mexican Independence Day in Chicago with this vibrant celebration of Mexican history, culture, and cuisine. The festival features traditional music and dance performances, authentic food and drink from dozens of vendors, artisan markets, and a festive atmosphere.

Explore more: Check out more Mexican Independence Day events and celebrations around the city.

Midway 5K (Sept. 13): Runners and walkers will get the rare opportunity to take over the airfield at Midway International Airport for a family-friendly race day like no other. There will be a 5K run, a 5K walk, and a mile event for kids.

Chicago Live! (Sept. 19 – 20): Navy Pier transforms into a vibrant stage for Chicago’s cultural community at this free performing arts festival representing music, dance, theatre, and more. The event will feature performances from more than 100 artists and groups, all open to the public.

Chicago Exhibition Week (September 14 – 20): Art lovers can explore more than fifty galleries and cultural spaces during this week-long celebration of Chicago’s thriving contemporary arts scene. Check the calendar for special programs, exhibition openings, artist conversations, and more.

Reeling Film Festival (Sept. 17 – 27): The second-longest-running LGBTQ+ film festival in the country, Reeling brings a diverse lineup of films that spotlight queer stories and underrepresented voices in cinema.

Englewood Jazz Festival (Sept. 17 – 19): For more than 25 years, the Englewood Jazz Festival has delivered three days of free, live music that highlights the long legacy of jazz on Chicago’s South Side and beyond.

International Greeter Day (Sept. 19): The Chicago Greeter program celebrates International Greeter Day with a full day of free pop-up walks. Meet in downtown Millennium Park before heading out to explore one of the city’s diverse neighborhoods with a friendly local.

Riot Fest (Sept. 18 – 20): One of Chicago’s most anticipated annual music festivals returns to Douglass Park with a powerhouse lineup featuring Twenty One Pilots, Iggy Pop, Morrissey, Alanis Morissette, and many more across multiple stages. The festival also features carnival rides, art installations, and a full schedule of after-shows.

Chicago Gourmet (Sept. 23 – 27): Chicago Gourmet, the city’s premier upscale food festival, brings together some of the city’s best culinary talent for a jam-packed weekend of tastings, demonstrations, and unforgettable bites in Millennium Park and beyond.

World Music Festival (Sept. 25 – Oct. 4): This annual festival showcases music and genres from around the world, with shows all around the city. The center of the festival takes place at the Chicago Cultural Center.

More events in Chicago this September

Summer fireworks at Navy Pier (Sept. 2 and 5): Don’t miss your last chance to catch the free Navy Pier fireworks before the summer season ends. The show lights up the sky every Wednesday and Saturday, with the Chicago skyline and Lake Michigan serving as the stunning backdrop.

The Great American Lobster Fest (Sept. 5 – 6): Fresh Maine lobsters are flown daily to Navy Pier for this lakefront seafood festival, featuring whole lobsters, lobster rolls, chowder, and more just steps from Lake Michigan. The fest also includes live music, cold drinks, and a full weekend of waterfront festivities.

Sound of Gravity (Sept. 3 – 6): Experience a boundary-pushing arts festival filled with immersive performances, live music, and interactive installations that highlight Chicago’s experimental creative scene.

North Coast Music Festival (Sept. 4 – 6): Dance the weekend away at this multi-day music fest, bringing the best in EDM, house, hip-hop, techno, and more to SeatGeek Stadium in nearby Bridgeview.

Taste of Polonia (Sept. 4 – 7): Get a taste of Chicago’s vibrant Polish heritage at the country’s largest Polish festival. Enjoy four days of live music, family activities, and of course, endless Polish cuisine, from pierogi to kielbasa and beyond.

79th Street Renaissance Festival (Sept. 6): This popular community festival is Auburn Gresham’s biggest and longest-running neighborhood tradition, featuring live entertainment, food, family fun, and local culture.

Throwback Music Festival (Sept. 11 – 13): Go back in time through five decades’ worth of iconic music, from classic rock and Motown to funk and pop. The lineup spans generations and genres, making for a fun and nostalgic outing for music fans of all ages.

German American Oktoberfest (Sept. 11 – 13): Oktoberfest comes to the heart of Lincoln Square, a neighborhood with deep German roots. This free street festival brings German food, beer, traditional music, folk dancing, and plenty of old-world charm.

Chicago Football Classic (Sept. 12): The Chicago Football Classic returns to Soldier Field, with Mississippi Valley State University taking on Lincoln University. There will also be a career fair connecting students with historically Black colleges and universities.

Printer’s Row Lit Fest (Sept. 12 – 13): One of the largest and oldest literature festivals in the Midwest, this free event features author readings, book signings, panel discussions, and hundreds of booksellers in the historic Printer’s Row area.

Ravenswood Art Walk (Sept. 12 – 13): More than 50 local artists will share their work through open studios, pop-ups, and an outdoor market during the Ravenswood Art Walk weekend.

Renegade Craft Fair (Sept. 12 – 13): Shop more than 400 independent makers, artists, and designers from Chicago and beyond. Browse a thoughtfully curated selection of handmade goods spanning jewelry, clothing, ceramics, and art prints.

Old Town Oktoberfest (Sept. 18 – 20): The charming streets of Old Town come alive with the sights, sounds, and flavors of Bavaria at this Oktoberfest celebration. Expect steins of German beer, bratwurst and schnitzel, traditional folk music, and lively stein-holding contests.

Retro on Roscoe (Sept. 18 – 20): A tradition for more than 30 years, this Roscoe Village throwback extravaganza is packed with live music, a classic car show, vintage shopping, and old-school fun for all ages.

Lakeview East Festival of the Arts (Sept. 19 – 20): This annual arts festival showcases more than 150 artists and their work, spanning photography, furniture, jewelry, paintings, and more. There will also be plenty of kid-friendly activities, live music, and food and drink options.

Jack’s Pumpkin Pop-Up (starts September 19): Chicago’s most over-the-top Halloween experience is back, and it’s bigger than ever. Jack’s Pumpkin Pop-Up features a giant corn maze, carnival games, axe throwing, food trucks, and an abundance of pumpkin-themed fun across a sprawling outdoor venue.

World Dumpling Festival (Sept. 19 – 20): With a new location in Lincoln Park, the World Dumpling Festival celebrates Chicago’s international culinary scene through the universal language of dumplings, from bao and pierogi to empanadas and gyoza.

Rhinoceros Theater Festival (Sept. 20 – Oct. 29): A tradition in the city’s independent theatre community for more than three decades, the Rhinoceros Theater Festival is Chicago’s longest-running fringe theatre event.

Chicago River Swim (Sept. 20): Now in its second year, the Chicago River Swim is already becoming one of the city’s most talked-about fall traditions. Spectators can cheer on swimmers along the Chicago Riverwalk from Lake Street to State Street.

Chicago Wellness Week (Sept. 21 – 27): This inaugural citywide wellness festival focuses on health, movement, and community. Check out everything from yoga and Pilates to mental health panels and nutrition workshops.

Chicago Underground Film Festival (Sept. 23 – 27): The longest-running underground film festival in the world shines a spotlight on the defiantly independent filmmaker. Screenings cover documentaries, world premieres, and experimental formats.

African/Caribbean International Festival of Life (Sept. 25 – 27): This Washington Park festival is dedicated to the culture and traditions of African and Caribbean nations. Enjoy three days of live music, traditional dance, authentic cuisine, and artisan vendors representing the diversity of the African diaspora.

Hyde Park Jazz Festival (Sept. 26 – 27): This legendary free jazz festival takes over historic Hyde Park with non-stop performances all weekend, featuring a mix of Chicago jazz legends and rising stars across multiple neighborhood venues.

Beverly Art Walk (Sept. 26): The annual Beverly Art Walk showcases a variety of local artists and their work through local demonstrations, home studio tours, and permanent public art throughout the Beverly neighborhood.

WingOut Chicago (Sept. 26 – 27): WingOut Chicago is back in Wrigleyville for the city’s ultimate chicken wing cookout, with creative and craveable flavors from the city’s top wing purveyors.

Randolph Street Market (Sept. 26 – 27): Browse vintage finds, antiques, and local artisan goods at this bustling European-style market in the West Loop neighborhood.

Chicago is home to one of the country’s most exciting theatre scenes, from Tony Award-winning theatres and cutting-edge original productions to the latest Broadway hits and everything in between. And for theatre lovers, fall is one of the best times of year to experience it all.

As the season gets underway, Chicago’s stages come alive with a packed lineup of fresh productions representing a wide variety of genres. There’s plenty to look forward to, so check out a few of the season’s upcoming highlights and get your tickets today.

Advance Man: Part One of the Honeycomb Trilogy at Strawdog Theatre Company

Aug. 14 – Sept. 27, 2026
This chilling sci-fi drama follows fictional astronaut Bill Cooke, who completed the first manned mission to Mars and returns with secrets and illicit cargo. His decisions will alter his family’s lives and humanity as a whole. This play is the first installation of an ambitious two-year project.
Get tickets to Advance Man

Vape! The Grease Parody at Apollo Theater Chicago

Aug. 20, 2026 – Jan. 3, 2027
Relive the joy and nostalgia of Grease through a haze of strawberry-scented vapor and a TikTok filter. This reimagined classic includes all the music, dancing, and innuendo that you remember, with a modern twist that’s irreverent, camp, and all fun.
Get tickets to Vape! The Grease Parody 

The Birth of the Pill at TimeLine Theatre

Sept. 2 – Oct. 4, 2026
Based on the book by Jonathan Eig, this gripping original drama traces the history of the scientists, activists, and philanthropists who helped develop a ground-breaking contraceptive option and the women who paid the price for social advancement.
Get tickets to The Birth of the Pill

Black Girl From a White Suburb at American Blues Theater

Sept. 4 – Oct. 4, 2026
Based on her memoir detailing the microaggressions and code-switching of being the only Black girl in a white Chicago suburb, this one-woman show uses storytelling and humor to explore how she found her voice in a hostile environment.
Get tickets to Black Girl From a White Suburb 

You Can’t Fake the Funk: A Journey Through Funk Music at Black Ensemble Theater

Sept. 5 – Oct. 25, 2026
Groove to the high-energy sounds of classic ‘70s and ‘80s funk bands, including Sly and the Family Stone; Earth, Wind and Fire; and Parliament Funkadelic. Discover the history of the genre while singing along to the era’s greatest hits at this energetic musical production.
Get tickets to You Can’t Fake the Funk 

The Attic at Goodman Theatre

Sept. 5 – Oct. 4, 2026
Experience the thrill of trapeze and modern circus art, complete with daring aerial feats, in this unconventional production. The moving new work is inspired by Shana Carroll’s memoir on her life as a trapeze artist and Tony-Award winning choreographer.
Get tickets to The Attic

Jekyll & Hyde at Broadway Playhouse

Sept. 8 – Oct. 25, 2026
Follow the haunting tale of a 19th-century scientist who unknowingly releases an evil alter ego, set to gothic pop-rock tunes in this acclaimed musical production. This production follows a completely sold-out and extended-by-demand run in Chicago last year.
Get tickets to Jekyll & Hyde

Dirty Dancing: The Musical at Nederlander Theatre

Sept. 9 – 20, 2026
Based on the beloved ’80s movie, this production combines electrifying dance choreography with songs from the original film for the ultimate nostalgic experience.
Get tickets to Dirty Dancing: The Musical

Play On! At Chicago Shakespeare Theater

Sept. 11 – Oct. 18, 2026
This innovative production infuses Twelfth Night, Shakespeare’s classic comedy, with the legendary jazz music of Duke Ellington. The action unfolds in Harlem during the swinging 1930s. This Tony-nominated jazz musical features iconic Ellington tunes like “It Don’t Mean A Thing” and “Don’t Get Around Much Anymore.”
Get tickets to Play On!

How We Got On at Definition Theatre

Sept. 11 – 27, 2026
Set during the 1980s, three suburban teens use the newly emerging sounds of hip hop to weave lyrics and rhythms that reflect their lives and desires for fame and success. An art installation, “The Sound Barriers Vol. 4,” runs alongside the production.
Get tickets to How We Got On

Destinos Chicago International Latino Theater Festival

Sept. 14 – Oct. 11, 2026
The 9th annual Destinos International Latino Theater Festival showcases Latino theatre companies from Chicago and across the country. Choose from a variety of works staged at some of the city’s top independent theatre venues.
Get tickets to Destinos

Kowalski at Lookingglass Theatre Company

Sept. 15 – Oct. 25, 2026
An imaginary meeting between playwright Tennessee Williams and a young Marlon Brando serves as the premise for this fascinating drama. The show, starring award-winning actor Johnny Galecki, will examine the artistry and creative collaboration behind the historic play A Streetcar Named Desire.
Get tickets to Kowalski

TopDog/Underdog at Steppenwolf Theatre Company

Sept. 17 – Nov. 1, 2026
This Pulitzer Prize-winning play follows the riveting lives of brothers Lincoln and Booth, two Black men trying to stay afloat in the dangerous American political and social landscape. Tony Award-winner Kenny Leon directs this fast-paced production.
Get tickets to TopDog/Underdog

Operation Mincemeat: A New Musical at CIBC Theatre

Sept. 29 – Oct. 11, 2026
Set during World War II, this rollicking, award-winning musical follows the true story of how a dead body, a fake love letter, and the James Bond novelist Ian Fleming changed the course of history. The production, currently on a world tour, was nominated for four Tony Awards in 2025.
Get tickets to Operation Mincemeat

Don Giovanni at Lyric Opera

Oct. 10 – Nov. 1, 2026
One of opera’s most famous anti-heroes is brought to life with all the intrigue and deceit that this powerful drama requires. Prepare to be swept up by the intensity and sharp humor of this beloved opera.
Get tickets to Don Giovanni

More shows coming to Chicago this fall and beyond

• Sunday in the Park with George at Chopin Theatre (now through Nov. 1, 2026)
• Birds of North America at Red Orchid Theatre (Sep. 10 – Oct. 04, 2026)
• Pandemonium, Please Hold at The Second City (now through Dec. 5)
• A Strange Loop at Raven Theatre (Oct. 8 – Nov. 8, 2026)
• Adirondack Chair Circle at Steppenwolf (Oct. 22 – Dec. 6, 2026)
• Carmela Full of Wishes at Chicago Children’s Theatre (Oct. 24 – Nov. 15, 2026)
• David Parr: Time Traveler at Chicago Magic Lounge (Wednesdays from Oct. 7 – Dec. 16, 2026)
• A Christmas Carol at Goodman Theatre (Nov. 13 – Dec. 31, 2026)
• Tituba at Court Theatre (Dec. 10 – 20, 2026)