10 Events You Can’t Miss In Chicago This May

Spring has sprung and Chicago is a beautiful place to be right now! From outdoor bars and restaurants to museums and theaters, there’s something to do around every corner in the Windy City. So we rounded up 10 events that’ll help you make the most of our beautiful city this month.



10. Chicago Beer Classic

Things To Do Chicago May

Chicago’s largest beer festival is back! Join us at Chicago Beer Classic on May 5th at Soldier Field. 75+ breweries, 150+ beers, the can’t miss summer kick-off event! Tickets on sale NOW 🍻 See you on the field.


9. Hayley Kiyoko Concert


That’s right! Hayley Kiyoko is coming to the House of Blues this Thursday, May 3. This show is on my must-see list and the House of Blues is always a great venue to check out! Check out the tickets here and I’ll see you there!


8. 360 Chicago


Experience this beautiful city from a completely different perspective by visiting the 94th floor of the John Hancock Building. The observation deck allows you to see 360 degree views of our city skyline, learn about Chicago’s history and is home to the moving platform thrillride TILT.


7. Vintage Garage Flea Market


If you haven’t check out Vintage Garage yet, the May 20th event is the time to do it! The theme of antiques this month is Midcentury Modern, so expect to see lots of vintage clothing, furniture, jewelry, kitsch, and nostalgia from the 40’s, 50’s and 60’s. It really is so fun and you can find great items every month.

 6. Kentucky Roller Derby Day


Come to Chicago Athletic Club on May 5th to witness the “most exciting two minutes in sports”, while experiencing the most exciting 2 hours on wheels at our Roller Rink! Both sessions bringing you the best of the Kentucky Derby (the Mint Juleps, that is), with the 4 pm session live streaming the big race and the 7 pm session reveling in the afterglow. Grandiose hats highly encouraged. You can even embrace your inner jockey as you skate around on an inflatable horse-on-a-stick, for purchase at the event while they last.

5. Wrigley Field


If you haven’t made it out to Wrigley Field for a Chicago Cubs game yet, May is the month to go! The temperature is comfortable and everyone is thrilled to be outside basking in the shining sun for the first time in months. Especially now that the Cubs won the 2016 World Series, there’s even more reason to support the team! Check out their schedule to find a game that fits your schedule – luckily there are a lot of them.


4. Feminist Prom


Relive (or replace) your high school prom memories at Rebellious Magazine’s annual Red & Wild Feminist Prom fundraiser event May 19th. Enjoy the music, dancing and fun of prom without the drama and help a good cause in the process – independent, woman-owned feminist media in Chicago.


3. Lost Lake

lost-lake-Chicago-tiki-barIf you feel the need to mentally escape while stuck in the city this month, check out a local tiki bar decked out in palm leaves – Lost Lake. Enjoy tropical cocktails and cuisine while basking in the relaxed ambiance and surrounding flower arrangements, feeling as if you’ve escaped to a tropical island.


2. Covet Market


Head out to Revel Fulton Market to check out over eighty local vendors and artists this weekend. Enjoy and support the artistry of our local designers and boutiques – from pantry goods to clothing and jewelry! Shop, eat, sip, walk around and revel in the creativity of other Windy City entrepreneurs.


1. Strip Joker


You can tell from the title itself that this event is SO much fun! Who doesn’t love a comedy show? And even better – Strip Joker is in a safe space where comedy isn’t homophobic, sexist, transphobic, ableist, racist or hurtful to any group of people. Come out and enjoy a body positive night of comedy May 12th.


These are just a few things that popped up on my radar this month – keep your eye out for other fun things to do in Chicago! Will I see you at one of these events?


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