Best in Trivia Rescue

Whaddayaknow? is proud to support our local community and its philanthropic efforts hosted by groups like ALIVE Rescue.

We’ve even joined as a co-presenting sponsor with Bernese Builder for this year’s event, as it’s near and dear to both of our hearts.

This year marks the 6th annual Best in Rescue event, and there’s lots of ways for you (and your pets) to participate!

• Think your pet has what it takes to earn the crown? Visit this link or scan the QR code on the flyer below to enter your animal in the “Donate to Vote” event before May 31 at 11:59 p.m. CDT! Your $20 donation includes 20 votes to help get your campaign going.
• Don’t have a pet? You can still make a difference! For just $1/vote between June 1-20, you can help Alive Rescue support homeless animals in the area AND decide which contestant best personifies the prestigious title of Best in Rescue 2026!

While Whaddayaknow? Free Pub Trivia provides countless opportunities for human enrichment each week, we can’t leave out our furry, feathery, or scaly friends! Below are just a few of our favorites.

Meet Asia

With a government name like Miss Asia Pinky Fuzzy Cat and a side eye to match, this fancy feline is always fishing for attention. She’s keeping Whaddayaknow? host Bryson’s favorite blanket warm while he’s working the crowd at AliveOne or Carol’s Pub.

Meet Jake

One of these things is not like the others, but Jake is a combination of one of the best types of humans. When he’s not evoking knowledge and excitement on the mic at at Gannon’s Pub, you can find him closely connected to ALIVE Rescue, a state-of-the-art non-profit and animal safe haven right here in Chicago.

Questions?

Lindsay Ritenbaugh serves as the Lead Content Strategist for Whaddayaknow? Free Pub Trivia. Coupled with a background in elementary and higher education, her Whaddayaknow? story began in 2013. She joined the Southern Comfort team of co-workers and fellow Florida/Georgia transplants at Merkle’s Bar & Grill and the rest was history! Even during a brief relocation back to Florida, Lindsay remained closely connected thanks to the company's virtual bingo and trivia offerings in 2020. She's spent the last five years playing (and hosting!) trivia throughout the Lakeview East, Lincoln Park, Southport Corridor, and Wrigleyville neighborhoods.

In her role as content lead, Lindsay now brings the fun of trivia to life by sharing stories that highlight the energy and camaraderie of the game. In addition to keeping players up to date on upcoming Whaddayaknow? events and special happenings, she channels her love of storytelling into content that resonates with both devoted trivia fans and curious newcomers alike.

Compete against Lindsay and the Washington Generals Tuesdays at The Butcher’s Tap, if you dare. Or start your own team and weekly tradition Wednesdays at Friar Tuck, where you can experience her endearing teacher voice live on the mic.

ChicaGO Pokémon

Can’t make it to Pokémon GO but interested in learning more about Pokémon-related activities in your area? All events on Chicago Pokémon’s site are officially sanctioned through the Play! Pokémon program, giving Pokémon fans opportunities to meet other Trainers and compete in an organized setting.

Gotta Win ‘Em All!

Whaddayaknow? Free Pub Trivia jumped at the chance to help provide a legendary Pokémon experience and kick off Pokémon GO Fest 2026, Chicago style:

Lindsay Ritenbaugh serves as the Lead Content Strategist for Whaddayaknow? Free Pub Trivia. Coupled with a background in elementary and higher education, her Whaddayaknow? story began in 2013. She joined the Southern Comfort team of co-workers and fellow Florida/Georgia transplants at Merkle’s Bar & Grill and the rest was history! Even during a brief relocation back to Florida, Lindsay remained closely connected thanks to the company's virtual bingo and trivia offerings in 2020. She's spent the last five years playing (and hosting!) trivia throughout the Lakeview East, Lincoln Park, Southport Corridor, and Wrigleyville neighborhoods.

In her role as content lead, Lindsay now brings the fun of trivia to life by sharing stories that highlight the energy and camaraderie of the game. In addition to keeping players up to date on upcoming Whaddayaknow? events and special happenings, she channels her love of storytelling into content that resonates with both devoted trivia fans and curious newcomers alike.

Compete against Lindsay and the Washington Generals Tuesdays at The Butcher’s Tap, if you dare. Or start your own team and weekly tradition Wednesdays at Friar Tuck, where you can experience her endearing teacher voice live on the mic.

Welcome to the online version of our monthly newsletter! Another copy likely exists in your inbox.

It’s Gonna Be May!

Spring has sprung, and it’s brought with it some important Whaddayaknow? updates:

We Derbied with Parlay

A large group of Whaddayaknow? Free Pub Trivia hosts and players alike took part in celebrating the Derby the Parlay way, enjoying free table reservations, 20% off tabs, and pre-race trivia at Parlay – Lincoln Park (950 W. Wrightwood Ave)!

Participants also had the chance to opt in for games of chance and luck ahead of the Kentucky Derby race.

Congratulations to Dominique Caldwell and Laura Reighard, who both correctly chose the first place horse Golden Tempo!

Additional prizes went to those who placed their bets on second and third place finishers Renegade and Ocelli:

• • Kat Abbas
  • Abbi Allen
  • Dustin Davis
  • Skyler Messinger
  • Lindsay Ritenbaugh

Be on the lookout for new opportunities to connect with Whaddayaknow? Free Pub Trivia at an upcoming event.

Calling All David Byrne Fans and Music Nerds

Qualifying Games for TOC XXVIII Continue

Last month, we announced the launch of our biannual Tournament of Champions qualification period. Will your team earn a coveted spot?

Competitions For All Ages

As we spring forward, we are actively looking to grow our partnerships with retirement communities and senior living facilities. To prepare for this new venture, we’ve got new content perfectly suited for these types of events.

If you or anyone you know works with a community like this and might be interested in adding trivia to their activity schedule, we’re ready to help make this process seamless and enjoyable.

Everything’s Coming Up Trivia

April showers bring May flowers new and recently added locations, including one date change from Saturday to Thursday for recurring games at Cheba Hut Wrigleyville.

Click through the tabs to view the following:

• ALL New Events
• New MUSIC BINGO Events
• New TRIVIA Events
• New Events on TUESDAYS
• New Events on WEDNESDAYS
• New Events on THURSDAYS
• New Events on FRIDAYS
• New Events on SATURDAYS

May Theme Nights

Finally, are you dying to flex your expertise of a niche topic? Here’s what’s on the schedule this month in Chicago and across the state:

As always, updates will be shared here at freepubtrivia.com. And be sure to follow us on social media!
Take advantage of the weekly Facebook/TikTok and daily Instagram social media bonus questions:

THANK YOU so much for your continued support – both live and virtually!

Have some feedback, suggestions, or just want to say hi?

Lindsay Ritenbaugh serves as the Lead Content Strategist for Whaddayaknow? Free Pub Trivia. Coupled with a background in elementary and higher education, her Whaddayaknow? story began in 2013. She joined the Southern Comfort team of co-workers and fellow Florida/Georgia transplants at Merkle’s Bar & Grill and the rest was history! Even during a brief relocation back to Florida, Lindsay remained closely connected thanks to the company's virtual bingo and trivia offerings in 2020. She's spent the last five years playing (and hosting!) trivia throughout the Lakeview East, Lincoln Park, Southport Corridor, and Wrigleyville neighborhoods.

In her role as content lead, Lindsay now brings the fun of trivia to life by sharing stories that highlight the energy and camaraderie of the game. In addition to keeping players up to date on upcoming Whaddayaknow? events and special happenings, she channels her love of storytelling into content that resonates with both devoted trivia fans and curious newcomers alike.

Compete against Lindsay and the Washington Generals Tuesdays at The Butcher’s Tap, if you dare. Or start your own team and weekly tradition Wednesdays at Friar Tuck, where you can experience her endearing teacher voice live on the mic.

Lindsay Ritenbaugh serves as the Lead Content Strategist for Whaddayaknow? Free Pub Trivia. Coupled with a background in elementary and higher education, her Whaddayaknow? story began in 2013. She joined the Southern Comfort team of co-workers and fellow Florida/Georgia transplants at Merkle’s Bar & Grill and the rest was history! Even during a brief relocation back to Florida, Lindsay remained closely connected thanks to the company's virtual bingo and trivia offerings in 2020. She's spent the last five years playing (and hosting!) trivia throughout the Lakeview East, Lincoln Park, Southport Corridor, and Wrigleyville neighborhoods.

In her role as content lead, Lindsay now brings the fun of trivia to life by sharing stories that highlight the energy and camaraderie of the game. In addition to keeping players up to date on upcoming Whaddayaknow? events and special happenings, she channels her love of storytelling into content that resonates with both devoted trivia fans and curious newcomers alike.

Compete against Lindsay and the Washington Generals Tuesdays at The Butcher’s Tap, if you dare. Or start your own team and weekly tradition Wednesdays at Friar Tuck, where you can experience her endearing teacher voice live on the mic.

If our recent Instagram Stories for social media bonus questions are any indication, we’re letting the good times cruise with Sun Cruiser! Whaddayaknow? is amped to join forces with Sun Cruiser as our official sponsor this year, especially because our founder Dan Burns hails from Boston. You’ll be hearing more from both of us online and through upcoming events, including Tournament of Champions XXVIII on August 8!

The Summer of Sun Cruiser

You’ve likely already seen Sun Cruiser at our past events, and we’re including them in even more events for 2026. With summer just around the corner, we recently hosted a Sun Cruiser Kickoff at Tin Roof Chicago. Congratulations to “The BMOTS” team who earned the grand prize of bragging rights, a Sun Cruiser golf bag, and other Whaddayaknow? prizes!

And Now, A Word From Our Sponsor

Sun Cruiser is a new kind of hard tea made with real iced tea and real vodka. It’s refreshing and easy to drink with just a hint of sweetness. Not only are Sun Cruisers low in calories, vegan, gluten- and GMO-free, they’re made with real fruit juice and taste delicious! Plus, there’s more flavors than there are days of the week!

• Classic (Iced Tea + Vodka)
• Half & Half (Iced Tea + Vodka with Lemonade)
• Peach Iced Tea + Vodka
• Raspberry Iced Tea + Vodka
• Classic Lemonade + Vodka
• Pink Lemonade + Vodka
• Strawberry Lemonade + Vodka
• Blueberry Lemonade + Vodka

And with a 4.5% ABV and far less caffeine than a cup of coffee, they pair perfectly with any night of Whaddayaknow? Free Pub Trivia. Many of our locations already have Sun Cruiser in stock, so take advantage of these offerings before, during, and after your next game!

Even if you’re looking to stay in, our virtual trivia options allow you to enjoy Sun Cruiser from the comfort of your own couch (or WFH setup). Which will be your new favorite flavor?

Author’s note: Half & Half is the best one by far. Trust me.

Lindsay Ritenbaugh serves as the Lead Content Strategist for Whaddayaknow? Free Pub Trivia. Coupled with a background in elementary and higher education, her Whaddayaknow? story began in 2013. She joined the Southern Comfort team of co-workers and fellow Florida/Georgia transplants at Merkle’s Bar & Grill and the rest was history! Even during a brief relocation back to Florida, Lindsay remained closely connected thanks to the company's virtual bingo and trivia offerings in 2020. She's spent the last five years playing (and hosting!) trivia throughout the Lakeview East, Lincoln Park, Southport Corridor, and Wrigleyville neighborhoods.

In her role as content lead, Lindsay now brings the fun of trivia to life by sharing stories that highlight the energy and camaraderie of the game. In addition to keeping players up to date on upcoming Whaddayaknow? events and special happenings, she channels her love of storytelling into content that resonates with both devoted trivia fans and curious newcomers alike.

Compete against Lindsay and the Washington Generals Tuesdays at The Butcher’s Tap, if you dare. Or start your own team and weekly tradition Wednesdays at Friar Tuck, where you can experience her endearing teacher voice live on the mic.

We recently met Ethan Starr at SPORCLECON, and we’re excited to announce he’s published a book!

Billionaire Trivia

How much do you really know about America’s billionaires? Billionaire Trivia goes beyond the names in the media, providing a peek into the lives of over 250 of the wealthiest Americans. With chapters covering billionaires’ early years, hobbies, philanthropy, tattoos, stints in jail, and more, you will be sure to learn something new.

Lindsay Ritenbaugh serves as the Lead Content Strategist for Whaddayaknow? Free Pub Trivia. Coupled with a background in elementary and higher education, her Whaddayaknow? story began in 2013. She joined the Southern Comfort team of co-workers and fellow Florida/Georgia transplants at Merkle’s Bar & Grill and the rest was history! Even during a brief relocation back to Florida, Lindsay remained closely connected thanks to the company's virtual bingo and trivia offerings in 2020. She's spent the last five years playing (and hosting!) trivia throughout the Lakeview East, Lincoln Park, Southport Corridor, and Wrigleyville neighborhoods.

In her role as content lead, Lindsay now brings the fun of trivia to life by sharing stories that highlight the energy and camaraderie of the game. In addition to keeping players up to date on upcoming Whaddayaknow? events and special happenings, she channels her love of storytelling into content that resonates with both devoted trivia fans and curious newcomers alike.

Compete against Lindsay and the Washington Generals Tuesdays at The Butcher’s Tap, if you dare. Or start your own team and weekly tradition Wednesdays at Friar Tuck, where you can experience her endearing teacher voice live on the mic.

Ever wanted to cheat at pub trivia but didn’t want to break your host’s heart or tarnish your team’s reputation? We have the perfect solution.

Together, 826CHI and Whaddayaknow? Free Pub Trivia are calling all trivia fiends to assemble their smartest, most devious friends for a chance to claim a trophy, medals, and ultimate bragging rights as Chicago’s best cheating trivia team. All proceeds will support Chicago students in building writing confidence, becoming published authors, and helping CPS teachers foster a love of writing in the classroom.

Chicago-based comedian and writer Eunji Kim will throw down the gauntlet in a battle of brains as the host of Trivia for Cheaters, a fundraiser for 826CHI. 

Cheating? For a Fundraiser? Groundbreaking.

This one-of-a-kind fundraiser invites teams to raise money to build a “cheat bank” which can be used to “buy” advantages such as peeking at answers, using phones, or sabotaging other teams. The result is a fast-paced, chaotic, and hilarious evening in support of 826CHI’s tuition-free writing programs for youth across Chicago.

How to Join

About 826CHI

Founded in 2005, 826CHI is a 501(c)(3) nonprofit writing, tutoring, and publishing organization dedicated to supporting students ages 6 to 18 with their creative and expository writing skills and to helping teachers inspire their students to write. As part of the 826 National network launched by author Dave Eggers and educator Nineve Clegari, services are structured around understanding that great leaps in learning can happen with individualized attention, and that strong writing skills are fundamental to future success. 826CHI’s student-centered, inquiry-driven methods, paired with our emphasis on publishing, gives students the tools they need to write their own paths forward.

Bringing Whaddayaknow? to Your Community

Aside from Chicago’s premiere bar trivia, we love partnering with community fundraisers like 826CHI across the Chicagoland area. If you (or someone you know) helps coordinate programming and are looking for something engaging, reliable, and genuinely fun, we’d love to connect.

We’re happy to:

• Share references

• Walk through program options

• Customize a recurring event schedule

• Or set up a one-time special night to test the waters

Lindsay Ritenbaugh serves as the Lead Content Strategist for Whaddayaknow? Free Pub Trivia. Coupled with a background in elementary and higher education, her Whaddayaknow? story began in 2013. She joined the Southern Comfort team of co-workers and fellow Florida/Georgia transplants at Merkle’s Bar & Grill and the rest was history! Even during a brief relocation back to Florida, Lindsay remained closely connected thanks to the company's virtual bingo and trivia offerings in 2020. She's spent the last five years playing (and hosting!) trivia throughout the Lakeview East, Lincoln Park, Southport Corridor, and Wrigleyville neighborhoods.

In her role as content lead, Lindsay now brings the fun of trivia to life by sharing stories that highlight the energy and camaraderie of the game. In addition to keeping players up to date on upcoming Whaddayaknow? events and special happenings, she channels her love of storytelling into content that resonates with both devoted trivia fans and curious newcomers alike.

Compete against Lindsay and the Washington Generals Tuesdays at The Butcher’s Tap, if you dare. Or start your own team and weekly tradition Wednesdays at Friar Tuck, where you can experience her endearing teacher voice live on the mic.

Lindsay Ritenbaugh serves as the Lead Content Strategist for Whaddayaknow? Free Pub Trivia. Coupled with a background in elementary and higher education, her Whaddayaknow? story began in 2013. She joined the Southern Comfort team of co-workers and fellow Florida/Georgia transplants at Merkle’s Bar & Grill and the rest was history! Even during a brief relocation back to Florida, Lindsay remained closely connected thanks to the company's virtual bingo and trivia offerings in 2020. She's spent the last five years playing (and hosting!) trivia throughout the Lakeview East, Lincoln Park, Southport Corridor, and Wrigleyville neighborhoods.

In her role as content lead, Lindsay now brings the fun of trivia to life by sharing stories that highlight the energy and camaraderie of the game. In addition to keeping players up to date on upcoming Whaddayaknow? events and special happenings, she channels her love of storytelling into content that resonates with both devoted trivia fans and curious newcomers alike.

Compete against Lindsay and the Washington Generals Tuesdays at The Butcher’s Tap, if you dare. Or start your own team and weekly tradition Wednesdays at Friar Tuck, where you can experience her endearing teacher voice live on the mic.

The W? Tournament of Champions XXVIII

Don’t miss out on the chance to participate in the 28th edition of the Whaddayaknow? Tournament of Champions in Chicago, one of America’s largest trivia team trivia events!The TOC has been held since 2011 and has now grown to support over 1000 players across over 100 bars in the Chicagoland area.

The qualifying round begins the week or March 22nd at all weekly, general knowledge locations. It last 10 weeks, and each team’s top 6 scores are summed for a tourney score (i.e. if a team attends all 10 weeks, its lowest 4 scores will be dropped).

The teams with the top cumulative tourney scores from each venue will receive invitations to represent their locations at the main event!

The main TOC event will be held on Saturday, August 8th at Joe’s on Weed, King’s Dining & Entertainment, and potentially a third location in Lincoln Park, Chicago.

Prove you’re the top trivia team in the city!

Play against over nearly 200 other teams for your chance to win gift cards, Sun Cruiser swag, or even our $2000 grand prize!

No matter how well you do at the big event, it’s always an absolute blast, complete with giveaways, great music, your favorite trivia hosts, drink specials, and even karaoke at our afterparty!

Information on your current standings at your regular bar can be found at:
https://freepubtrivia.com/toc-standings/

Make sure you play your location frequently, get your email address to your trivia host, and use the same team name throughout the qualifying weeks to ensure your position at this summer’s Whaddayaknow? Tournament of Champions XXVIII on Saturday August 8th!

The Enablers win it all at our last summer tourney