10 Actually Fun Things to Do in Chicago This Weekend

The Bears, the bands, the brunch, the beach, and the burlesque.

It may be Pitchfork weekend, but that’s not to say the annual hipster-palooza is the only game in town. There’s also the African/Caribbean Festival of Life, a burlesque show for hurricane relief, a volleyball tourney benefiting Special Olympics Chicago, and a Bears block party taking over Logan Square to kick off the 2021 season. Strap in, folks. Here’s everything fun you can do in Chicago this weekend.

Stick a fork in your tired old playlist at Pitchfork Music Festival

Friday, September 10 - Sunday, September 12
Union Park
Pitchfork makes its triumphant return to Union Park with a new September dance card, and the weather should not disappoint. Headliners include Erykah Badu, St. Vincent, Angel Olsen, and Phoebe Bridges, with a predictably strong roster of supporting acts including Animal Collective, Flying Lotus, Thundercat, and more. And we haven’t even mentioned the onsite record, poster, and craft fair and luxe food and drink options yet. You know what to do.
Cost: Passes start at $90 per person

Greek out at Lincoln Park Greek Fest

Friday, September 10 - Sunday, September 12
St. George Greek Orthodox Church
This family-friendly event sets up shop outside St. George Greek Orthodox Church for Greek (and non-Greek) musical acts, food, crafts, and Greek dance lessons for those who want to get in on the action. There’s also a drive-through food option for those who prefer to do their partying contactless.
Cost: Admission runs $10 per person (suggested donation); vendor prices vary

Ponder the burning question of our time at 20x2 Chicago: What Now?

Saturday, September 11
20x2 Chicago returns to the Schubas stage for another wonderfully unusual evening in which 20 local artists, writers, and creatives each have two minutes to answer the same question in whatever form they choose. This edition’s question: “What Now?”
Cost: Admission runs $10 per person

Help hurricane victims by catching a burlesque show

Saturday, September 11
Newport Theater
Chicago’s top burlesque and drag performers are hosting this Saturday’s Big Easy Stripteasey, a relief benefit show to raise funds for fellow New Orleans performers impacted by Hurricane Ida. Do your part.
Cost: Admission runs $15 per person

Spend a day in the sand at Spike for Special Olympics Chicago

Saturday, September 11
North Avenue Beach
This benefit event for Special Olympics Chicago and Special Children’s Charities features beach volleyball teams of six to eight competing for prizes, with an afterparty at the one and only Castaways.
Cost: Admission starts at $5 per person

Bang it out at Chicago Metal Fair

Saturday, September 11
Hear tunes from top artists behind Chicago’s stoner metal and doom scene on the second floor of Reggie’s with music for sale alongside rare beers from Metal Monkey Brewing, video screenings, and a special “mind melt” table with rare VHS tapes and other appropriately weird ephemera.
Cost: No cover

Peruse an outdoor gallery at the Lakeview East Festival of the Arts

Saturday, September 11 - Sunday, September 12
Broadway from Belmont to Hawthorne
This pop-up arts festival along Broadway showcases works from more than 150 juried artists spanning paintings, sculptures, jewelry, photography, furniture, and more. Food, booze, and live music round out the experience.
Cost: Admission runs $5 per person (suggested donation); vendor prices vary

Don’t be a jerk at the International Festival of Life

Saturday, September 11 - Sunday, September 12
Washington Park
This year held in collaboration with the Jerk, Seafood, and Vegan Festival, the 28th annual African/Caribbean Festival of Life returns to Washington Park for two fun-filled days of live reggae and world music, food, arts, crafts, games, and more. Irie, mon.
Cost: Admission starts at $20 per person

Work out (before stuffing your face) at Chicago Gourmet’s Wellness Brunch

Saturday, September 11 - Sunday, September 12
Bar Siena
Chicago Gourmet continues to keep foodies satiated all September long with a number of specialty culinary events, including this weekend’s Wellness Brunch at Bar Siena. The boozy brunch feast follows a morning outdoor workout, so you won’t feel a tinge of guilt ordering that third mimosa.
Cost: Tickets run $48 per person

Bear down for the 2021 season at the Chicago Bears Block Party

Sunday, September 12
Milwaukee Avenue between Spaulding and Sawyer
Get an early jump on the action at this season opener outdoor tailgate along Milwaukee Avenue in Logan Square. Enjoy food and drink specials from neighborhood bars like Park & Field, Innjoy Logan Square, and Logan 11 Bar & Kitchen and watch the game on two giant projector screens.
Cost: No cover; vendor prices vary

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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.