Everything Fun You Can Do in Chicago This Weekend

These are all your local must-hit music and food festivals, events, movies, markets, deals, and concerts to help you make the most of your weekend.

As you rock an outdoor music festival outside Empty Bottle, attend a Friday fish fry at the world’s largest rooftop, and run around Wrigleyville in your underwear, you would be forgiven for asking yourself this question: “Is it really February in Chicago?” Yep, it really is. Here’s everything fun you can do in Chicago this weekend.

Friday, February 24
Midwest Coast Brewing
The concept is simple: Local comics perform two sets each. One set sober. One set drunk. The audience then votes for the funniest. How much you yourself drink is up to you.
Cost: $15

Friday, February 24 - Friday, April 7
Offshore Rooftop
Recognized as the world’s largest rooftop by the folks at Guinness World Records, Offshore celebrates the Lent season with its first in a series of Friday fish fry events featuring beer-battered pike, Texas toast, and fries.
Cost: $25

Saturday, February 25
Western & Cortez
Empty Bottle hosts its annual winter block party outside the iconic venue with live bands including Meat Wave, Special Interest, and Snooper plus booze from Goose Island and donations accepted for the Chicago Coalition for the Homeless.
Cost: Free (donations accepted)

Saturday, February 25
Sluggers
This annual winter charity fundraiser will have you drinking, dancing, and running around Wrigleyville in your underwear. Dance party to follow the one mile-ish run. Who needs online dating when there’s this?
Cost: $45

Saturday, February 25
Promontory
What would happen if you combined the astrological signs of Pisces and Aquarius? Find out at this cocktail-fueled dance party with live DJs spinning to a well-heeled crowd in suits and evening gowns (preferred but not mandatory).
Cost: $20 - $50

Saturday, February 25
Epiphany Center for the Arts
Event organizers proclaim “niceness guaranteed” at this reggae vibes show featuring local artists including Urban Rhythm Reggae Band and Vision in the Rhythm paying tribute to Bob Marley.
Cost: $15 donation

Saturday, February 25
Navy Pier
Carnivale traditions from around the world including Brazil, Colombia, Jamaica, Italy, and Puerto Rico will be showcased at this internationally-flavored celebration with live music, art making, food and beverages.
Cost: No cover

Sunday, February 26
Emporium Wicker Park
A breakdancing party? In an arcade bar? On a Sunday? What, you got better things to do? This event includes a live dance off plus afterparty with 3x DMC World Champion and Slow Roast Records founder Craze.
Cost: $10

Now through Sunday, February 26
Various locations
The Chicago Independent Venues League (CIVL) hosts this multi-venue live music and performance festival in support of local indie venues. The festival closes out this weekend with shows at Hungry Brain, Sleeping Village, Patio Theatre, and more.
Cost: Varies

Now through Sunday, February 26
Various locations
Nab value-priced tickets to more than 100 performances at theatres across the city from Second City and Blue Man Group to Chicago Shakespeare Theater and Broadway in Chicago. If you can’t find something new to dig here, you’re probably napping in your seat.
Cost: $15 - $30 per show

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Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile.