Casa Humilde and Stolen Saddle will NOT be hosting events today, August 7

Trivia Feud at InnJoy Wicker Park every Thursday!

Love Whaddyaknow and Pub Trivia? Take it to the next level at SporcleCon - three days of live games, brainy competition with over $10k in prizes, and trivia-fueled fun - all coming to Chicago this summer! 


Join players from around the country for the ultimate trivia weekend!
August 15–17 | McCormick Place, Chicago

We will be running our game on Saturday the 16th at 2pm! 

Join Us For SporcleCon on August 16th! Save 10% With Our Exclusive Code!

Qualifying teams, we look forward to seeing you on 

Get Ready for TOC XXVI! The biggest event of the season is FRIDAY August 9th!

for a list of our participating locations!

Win Riot Fest Tickets at Whaddaknow? Music Bingo Events!

Wondering if your next trivia night is cancelled? Looking for special events? We got you with information updated daily! Check out our 

You’re walking through a sea of Cubs jerseys worn by 20-somethings who have had 20-something beverages throughout the day. Lines and crowds roar around you. You’re desperate for a respite. You want a place where you can talk to your friends but instead you see nothing but standing-room-only crowds and a constant roar.

You go south on Sheffield and suddenly, an oasis appears. You walk in.

And enter, 

 in Chicago. You’ll smell the delicious fare of 

 (the Graystone sauce on their delicious chicken wings - a unique blend of BBQ and buffalo sauce - is to die for! But let’s not forget their epic smash burger either!) and feel the neighborhood vibes as you take a seat at the bar to be immediately greeted by the talented and friendly staff.

Where most bars in the area tend to focus on partying after a Cubs win, and are oft-times claustrophobic and raucous, Graystone is a neighborhood bar that contains multitudes. One night you see a community space filled with regulars gently teasing the staff and each other. The next, a screening of the Bachelor in the back bar and a bachelorette party in the front. No matter the time, day or night, you’ll find a great time, and more importantly, you’ll find a community.

For example, they support over half a dozen of teams, and do so full-throatedly. 

 athletics.

But maybe most importantly, they also have long been a supporter of 

 Team Trivia.

Opened in 2015 at 3441 N. Sheffield Ave., they greatly expanded their space with an enclosed patio area that is open year-long, with dozens of TVs that can show whatever game you want to see (as well as Whaddayknow? Trivia questions). Where they once had a concrete space with a few tables, they now have an enclosure with soft lighting and a brand new second bar with a warm wooden enclosure that’s perfect for college football screenings or tiki nights.

Just a stone’s throw away from Wrigley, it’s a great pre-game spot for Cubs fans, for their Columbus Crew soccer fanbase to see televised Crew games at one of the only bars in town that screens them, and on College Football weekends they go all out with their Washington and Kansas State game coverage.

As we’ve helped provide music and encouragement to a Washington and Kansas State football double-header, we can confirm it’s quite the experience to watch a game and hear the fight song after every touchdown for the team everyone there is to support. Graystone isn’t just a bar for its supporters, it’s a bar that excites supporters! When Washington made the playoffs in 2023, you could not BELIEVE the excitement from all the patrons who came out just to root their team on.

But they also know how to do trivia. We host our famous pub event trivia game 

 where our players get to take advantage of their great food offerings and drink selection while playing for $50 (for first place), $25 (for second) and a round of shots for third!

But that’s not all. The winning team gets a chance to win even more! Graystone holds a 

 game which, if you win, can result in a CASH PRIZE of anywhere from $100 to $1,000+ (if the game isn’t won the prize goes up each week until we have a winner!)

Over the years, we’ve gathered a great group of regular teams who constantly battle for trivia supremacy while soaking in the laughter and reasonably priced drinks at Graystone. The Chel-Kings, Weird Tuesdays, Sleepover! At the Grocery Store (who one week went as “Engaged! At the Grocery Store” - we’ll let you guess the subtext behind that) and so many more have become both foes and friends through our weekly trivia events.

They even host one of the most unique trivia experiences over the holidays. While many bars host Christmas pop-ups, Graystone decided to change things up…with 

! A Hanukkah pop-up event unlike any other! And yes, they still have trivia on every Wednesday during the event, with 

 like the “Mensch Mule” and “Gelt Martini.” They also update their 

 for the event for holiday-appropriate fare, with a variety of latkes, matzo ball soup, challah grilled cheese, and boozy jelly donuts (the last one isn’t quite a Hanukkah tradition, but this is a tavern after all).

Graystone is not only a breath of fresh air in the otherwise crowded and occasionally unwelcoming venues in the Wrigleyville area, offering a friendly staff, great service, neighborhood vibes and an 

, but they also have been home to many Whaddayaknow? events that our hosts have been able to enjoy.

We’ve hosted many team-building events at Graystone, including holiday parties, where the covered and heated patio area provides a spacious environment, and Chi Hunter does his thing, providing impossibly smothered nachos, delicious wings, tater tots, and much more! After we’ve given out our yearly rewards to our amazing Whaddayaknow? hosts, we can assure you no one leaves with an empty belly.

If you decide you’d like to 

? host, just know that Graystone is an amazing home base where you’ll always be welcome for a meticulously-crafted drink, perfectly-poured beverage, and a delicious meal while making friends in the calm of the storm that is Wrigleyville.


There are so many amazing bars and taverns in Chicago, and we are lucky enough to work with Graystone and 

Learn how to play trivia at one of Wrigleyville's BEST bars (and Hannukah pop-up) with the best vibes, drinks and food around!

Play Whaddayaknow? Trivia at Graystone Tavern, the Crown Jewel of Wrigleyville!

 one of our Music Bingo locations! EVERY music bingo round winner throughout 

 will win a raffle entry for that location (in addition to the regular prizes)! 

We're thrilled to be working with Chicago's BEST festival to give you a chance for music, food, games and fun.

Play as much W? Music Bingo as possible at as many places as possible all summer long for a great chance to win! 

Check our weekly music bingo schedule below!

Want tickets for Riot Fest 2025? Come to one of our music bingo events for a chance to win passes for Chicago's best music festival!

Riot Fest 2025 Ticket Giveaway!

 is coming this summer to Chicago from August 15-17th! Enjoy Whaddayaknow? and pub trivia! Take it to the next level at SporcleCon - three days of live games, brainy competition with 

, and trivia-fueled fun in downtown Chicago. Whaddayaknow? founder Daniel Burns will be featured on a 

panel discussing the business of bar trivia

 on Saturday, August 16th at 10:30 a.m.!

Join players from around the world for the ultimate trivia weekend!

, Chicago - play W? Trivia on August 16th at 1pm!

Use code WHADDAYAKNOW for 10% off all tickets at 

It's one of the biggest trivia weekends in the country - perfect for all you trivia buffs, and we have a discount code for you to join us and experience great trivia games from all over the U.S.!

SporcleCon is coming to Whaddayaknow?'s hometown of Chicago this summer from August 15-17th, and we will be repping with our game on Saturday the 16th! 

Since 1894, the Field Museum has been on the forefront of education and knowledge. So naturally, they know their way around a trivia event. That's why Whaddayaknow? is thrilled bring Chicago's iconic Field Museum to our locations every month from February to August!

There'll be big prizes, including memberships/deals, coupons and more. And every one of our partners hosting have agreed to be proud supporters of the Field!

Look below to see when you can help support the Field Museum while taking part in Chicago's BEST team trivia!

Monthly Whaddayaknow? Trivia Nights sponsored by the Field Museum!

We will be partnering with Chicago's iconic FIELD MUSEUM at a different one of our locations every month from February through August!

Welcome to the Home of America's Best Team Trivia Game

The perfect way to stay connected both in person and virtually!

Latest News

Recent News - July 19, 2025

Play Live Tonight

Riot Fest 2025

SporcleCon is coming to Whaddayaknow?'s hometown of Chicago this summer from August 15-17th, and we will be repping with our game on Saturday the 16th!

Whaddayaknow? Trivia Nights With the Historic Field Museum!

Play Live Tonight

Get Your Virtual Ticket Here

Games Every Tuesday and Thursday at 7pm CST

Bring W? to Your Venue

Upcoming Trivia Themes

New Themes coming shortly! Check back soon for more information.

Interested in Becoming a Host?

Find What You Need

Contact Us

Welcome to the Home of America's Best Team Trivia Game

The perfect way to stay connected both in person and virtually!

Latest News

Recent News - July 19, 2025

Play Live Tonight

Riot Fest 2025

SporcleCon is coming to Whaddayaknow?'s hometown of Chicago this summer from August 15-17th, and we will be repping with our game on Saturday the 16th!

Whaddayaknow? Trivia Nights With the Historic Field Museum!

Play Live Tonight

Get Your Virtual Ticket Here

Games Every .css-1tciydi{color:var(--chakra-colors-greenLogo-300);}Tuesday and Thursday at 7pm CST

Bring W? to Your Venue

Upcoming Trivia Themes

New Themes coming shortly! Check back soon for more information.

Interested in Becoming a Host?

Find What You Need

Contact Us

Games Every Tuesday and Thursday at 7pm CST