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 we kick off the first long weekend of summer, our hearts and minds are in Uvalde, Texas, mourning the 19 children and two adults who lost their lives in yet another mass shooting. If you’re feeling similarly hopeless and frustrated, know that there are ways to help the families of the victims, including donating blood and supporting verified fundraisers. You can also contact your Congress Members and demand sensible gun reform or get involved with organizations like Everytown that are working to prevent gun violence in America.

We get it if you’re not in the mood to celebrate this weekend, but we also think that getting outside and enjoying beautiful weather, spending time with loved ones, and remembering all of the things that make living in this city so great are some of the best ways to honor the memories of those who can no longer experience such simple joys. If you do decide to venture out, we’ve got a full slate of activities, including Chicago’s newest music fest and the Memorial Day Parade. Here’s everything you can eat, drink, and do in Chicago over the long weekend.

Thursday, May 26 - Monday, July 4
Emily Hotel
The wildly popular Rooftop Cinema Club finally makes it way to Chicago as it pops up on the fifth floor of the swanky Emily Hotel for a summer of romantic open-air screenings kicking off this weekend with Ferris Bueller’s Day Off, Pulp Fiction, The Great Gatsby, and more.
Cost: $19.75 - $27.75 per show

Friday, May 27
SPACE
WNUR 89.3 hosts this unique annual music fest which pairs out-of-town acts with local musicians in the spirit of experimentation and showcasing under-represented acts as a “physical manifestation of what WNUR seeks to do on the air.” So you should probably check it out if your playlist is getting a little stale.
Cost: $15

Friday, May 27 - Sunday, May 29
18th & Blue Island
Chicago’s biggest Memorial Day bash sets up shop in Pilsen for three fun-filled days of fine Mexican cuisine, lucha libre wrestling, three stages of live music headlined by Kinky, an authentic open-air market, and more. And yes, more mole dishes than you can shake a churro at.
Cost: $5 - $10 suggested donation

Friday, May 27 - Monday, September 5
Various locations
As per custom, beach season in Chicago officially kicks off Memorial Day weekend. So go carve your space in the sand at one of these top locations, or wherever the hell else you can find a spot. Might as well grab a drink while you’re at it.
Cost: Free

Saturday, May 28
Various locations
Memorial Day isn’t all about mattress sales and an extra hangover day. It’s also the time to honor America’s military veterans, which you can (and should) do by attending the Wreath Laying Ceremony at Daley Plaza followed by the Memorial Day Parade along State Street from Van Buren to Lake Streets.
Cost: Free

Saturday, May 28 - Sunday, May 29
Guaranteed Rate Field
The Sox host the Cubs during the second leg of the Crosstown Classic, with the Sox winners of the first two at Wrigley. Watch the Cubs try to even the score with this group outing which includes an upper deck ticket, all-you-can-eat pre-game tailgate buffet, and roundtrip shuttle from Reggie’s.
Cost: $65

Saturday, May 28 - Sunday, May 29
Belmont & Sheffield (obviously)
The biggest fest to kick off traditional Chicago summer street festival season is this long-running staple taking over Lakeview with a heady assortment of cover bands, original artists, live Aikido demonstrations, a drag show, and more.
Cost: $10 suggested donation

Saturday, May 28 - Sunday, May 29
Grant Park
Lollapalooza isn’t the only party happening in Grant Park this summer. The all-new Sueños Fest leans heavy on reggaeton and Caribbean-influenced music as Chicago’s newest entry into the city’s always sizzling summer music festival lineup.
Cost: $275+

Saturday, May 28 - Sunday, August 21
Navy Pier
Pixar fans will enjoy this new pop-up mini-golf experience from the fabled animated studio featuring 18 holes inspired by classic Pixar films, characters, and stories such as Toy Story, Finding Nemo, A Bug’s Life, and more. There’s also a weekend “After Dark” series for adults 18 and up.
Cost: $30.50+

Sunday, May 29
The Plant
Head over to Whiner Beer’s taproom at the Plant in Back of the Yards for this event featuring literary offerings from South Side bookstores including 51st Ward Books, Haymarket Books, and Pilsen Community Books plus live yoga classes, free plant-based cooking classes, and tours of the facilities.
Cost: Free

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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.