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A wings festival
Photograph: Courtesy of WingOut Chicago

The best things to do in Chicago this weekend

Find the best things to do in Chicago this weekend with our guide to concerts, exhibitions, festivals and more.

Jeffy Mai
Edited by
Jeffy Mai
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Welcome to another weekend! Take a load off by soaking in a spa or spending some time at the best Chicago attractions. Memorial Day weekend marks the unofficial start of summer, and you can attend the Memorial Day parade or catch a dazzling fireworks show at Navy Pier. Summer street fests are also back, with Mole de Mayo, the Belmont-Sheffield Music Festival and Mayfestiversary all happening. So ready to make the most of your time off? Check out the rest of the best things to do in Chicago this weekend.

RECOMMENDED: The best things to do in Chicago right now

Events and to do this weekend in Chicago

  • Music
  • Music festivals
  • Millennium Park

Started in 2022, this two-day extravaganza returns to Grant Park over Memorial Day weekend. Taking place on a single stage in Grant Park's Hutchinson Field, Sueños will feature headlining sets from Peso Pluma, Ivan Cornejo, Rauw Alejandro and Maluma. Other notable names on the lineup include Bad Gyal, Mora, Manuel Turizo, Xavi, Gabito Ballesteros and more.

In addition to two days of music, you can try food from some of Chicago's best Latin restaurants, a host of experiential activations and a Ferris wheel in the park that you can ride between (or during) sets. It's one of the largest new festivals to come to launch in Chicago in years and a fitting addition to a summer festival calendar that's more crowded than ever.

  • Things to do
  • Festivals
  • Lower West Side

Pilsen's annual Mole de Mayo street festival—which honors the traditional Mexican sauce with a mole cook-off, plus a market full of vendors—moves to a new stretch on 18th Street this year over Memorial Day weekend. Grab some enchiladas smothered in aromatic mole and don't miss the festival's lucha libra wrestling matches. 

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  • Things to do
  • Festivals
  • Lake View

Love cover bands? Head to Lakeview (right by the Belmont Red Line station) for three days of music, featuring local tribute acts like 16 Candles and Rod Tuffcurls & the Bench Press. A second stage hosts an eclectic array of community performers, plus karaoke with Trader Todd's. Plus, you'll find beer, wine and plenty of neighborhood vendors to browse while you hang out on the street.

  • Things to do
  • Festivals
  • North Center

Ravenswood Corridor neighbors Dovetail and Begyle return this year for their annual Memorial Day weekend street fest on Malt Row, where attendees can sip beer from both breweries and grab bites from Beard and Belly, Donerman, Happy Lobster and more. Catch live music and consider tossing in a donation, which will benefit neighborhood food pantry The Friendship Center. 

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  • Things to do
  • Festivals
  • Wrigleyville

They say that there's nothing more American than apple pie, but we're of the opinion that the most patriotic food of all is the chicken wing. Soaked in a variety of different sauces (from classic buffalo to Asian ginger, spicy garlic and honey chili), it's a versatile dish that has become a national staple. Taking place over Memorial Day Weekend, WingOut Chicago celebrates the venerable chicken wing, inviting cooks from Jake Melnick's, Smoke Daddy and more to put their spin on the dish. General admission includes entry and access to live entertainment, with the option to purchase a la carte wings and beverages. Opt for VIP tickets for early entry, all-you-can-eat wings and a drink package.

  • Things to do
  • Fireworks
  • Streeterville

During the summer, one of the best aerial displays you'll find in Chicago originates from Navy Pier. The Chicago attraction hosts twice-weekly fireworks shows (on Wednesdays and Saturdays) from Memorial Day weekend through Labor Day weekend, with stunning views available from across the pier's public spaces. Of course, you can also take in the show from nearby beaches or while cruising along the Lakefront Trail.

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  • Music
  • Jazz
  • Greater Grand Crossing

The South Side Jazz Coalition hosts a series of free monthly jazz performances every summer on the steps of St. Moses the Black Parish in Greater Grand Crossing. Bring a lawn chair, some snacks and prepare to hear some top-notch music from the Chicago jazz community—plus, every performance ends with a jam session. 

  • Things to do
  • Streeterville

Enjoy outdoor live music all summer long at the Navy Pier Beer Garden. The free series will feature local, regional and national acts performing countless genres and musical styles every weekend. Check the official Navy Pier website for the full schedule.

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  • Things to do
  • Loop

The musical adaptation of Robert Zemeckis’ 1992 cult classic Death Becomes Her gets its pre-Broadway premiere in Chicago. Running through June 2, the hilarious production stars Tony Award nominees Megan Hilty and Jennifer Simard, and is directed and choreographed by Tony Award winner Christopher Gattelli. The plot follows two women as they fight for the affections of the same man and drink a magic potion that promises eternal youth.

  • Kids
  • Suburbs

Bounce The City, an immersive family attraction featuring four interactive inflatables, will be popping up at Orland Square in Orland Park for a three-week run. Little ones and little ones at heart will be able to jump, slide and bounce their way through a 600-foot-long obstacle course, a skyscraper slide, a silent disco dome and more. Tickets start at $24 for a 90-minute pass.

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  • Things to do
  • Streeterville

Navy Pier, in partnership with the Design Museum of Chicago and The Vintage House Show Collective, presents a new exhibit exploring the history of the home-grown artists, clubs and labels that have built House music. The exhibit will be open and free to the public during all Pier operating hours through the end of October.

  • Things to do
  • Wicker Park

If dozens of vendors aren't enough of a draw for you to come to the lively Sunday market at this West Town neighborhood’s namesake park, maybe the weekly complimentary market programming—which includes free yoga, meditation and storytime for kids—will be. The market is also committed to sustainability, with plastic-free vendors and composting.

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  • Things to do
  • Suburbs

If you can withstand the roar of O'Hare traffic and incoming 747s (plus, you know, the trek on Chicago's most horrible freeway), you'll find some of the best deals in greater Chicagoland at this flea market outside Allstate Arena. Pick up odd trinkets or bulk candy and potato chips, plus clothing, housewares, furniture, jewelry and collectibles. Boasting over 700 sellers, this flea market is a favorite of vintage buyers themselves, so you know there are some great finds to be had at the fraction of city prices. Bring your best bargaining skills.

Green City Market Lincoln Park
  • Things to do
  • Markets and fairs
  • Lincoln Park

One of Chicago's most popular farmer's markets, Green City Market welcomes vendors selling regional produce to the south end of Lincoln Park (between Clark Street and Stockton Drive) on Wednesdays and Saturdays. Amid the rows, you’ll find farm-fresh eggs from Michigan, cheese from Wisconsin and scrumptious pies baked by Chicago’s own Hoosier Mama Pie Co.

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  • Things to do
  • Festivals
  • Loop

This annual festival assembles luminaries from the fields of politics, journalism and the arts for a multi-week series of programming across the city, with events ranging from lectures and discussions to screenings and musical performances. Not sure which events to hit? Some of the fest’s biggest speakers this season include former Supreme Court Justice Stephen Breyer, architect Jeanne Gang, musician Kathleen Hanna and comedian Reggie Watts. You can see a full schedule of programming on the Chicago Humanities Festival website.

  • Things to do
  • Hyde Park

The Museum of Science and Industry debuts a new exhibit dedicated to the science and technology behind the world’s longest-running film franchise, James Bond. Fans can check out 13 vehicles and over 90 additional artifacts, including the prototype jetpack used in Thunderball, an MI6 Retina Scanner from GoldenEye and the Parahawk snowmobile hybrid from The World Is Not Enough. You’ll also be able to step into a lab space inspired by “Q” and test your skills developing the perfect vehicle for spy activities, designing stunts and more.

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  • Things to do
  • Streeterville

Navy Pier’s newest attraction is here, transporting guests to some of Chicago’s most epic places via exhilarating flights. The multi-sensory experience incorporates drone technologies with aerial shots and first-person views to showcase the city like never before. Guests will swoop, dip and turn in motion seats as they climb up skyscrapers, check out iconic landmarks, float through fireworks and more.

  • Things to do
  • Skokie

Downton Abbey: The Exhibition makes its way to Westfield Old Orchard Shopping Center in Skokie, giving fans an opportunity to step into the world of the hit series. The immersive experience showcases the elaborate sets, detailed costumes and luxurious jewelry of Downton Abbey’s high society inhabitants, and transport visitors to the grand home of the Crawleys and those who served them. From Mrs. Patmore’s hectic kitchen and Carson’s office to the family’s glamorous dining room, the exhibition provides a fascinating look into the post-Edwardian period.

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  • Things to do
  • Skokie

The largest and most immersive touring Titanic exhibition comes to Westfield Old Orchard mall in Skokie. Visitors will experience a narrative journey that brings to light the fates of the passengers and crew aboard the famous ship. Marvel at hundreds of artifacts that survived the sinking, plus props and costumes featured in James Cameron’s blockbuster film Titanic. Music from the era will play as patrons walk through detailed recreations of the ship’s interiors, including the grand staircase, while the Discovery Gallery will simulate what discovery teams saw during dives to the Titanic’s wreckage site.

  • Things to do
  • Suburbs

Sony Pictures Entertainment has brought its first immersive entertainment destination to Oakbrook Center, inviting guests to enter the worlds of popular franchises like Uncharted, Ghostbusters, Jumanji, Bad Boys, Zombieland and more. The 45,000-square-foot space is home to a variety of activities, ranging from escape rooms to virtual reality and racing simulators to bumper cars. When you need to refuel, drop into the Commissary Restaurant for a full menu of food, desserts and cocktails. Entry to Wonderverse is free, with attractions priced separately.

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  • Art
  • Film and video

Displaying a 25-story-tall video installation on the side of THE MART, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. ART on THE MART's array of 34 digital projectors show the creations after dusk every evening. It’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

  • Sports and fitness
  • Yoga & Pilates
  • Streeterville

Head to 360 Chicago on Saturdays for yoga with a killer view. Instructor Britta Eumann will lead an hour-long class on the 94th floor of 875 N Michigan Avenue (formerly the John Hancock Center) that’s suitable for all ages and skill levelsyou just need to bring your own mat and arrived properly dressed. Registration is $55 and includes a cocktail or coffee, plus admission to the observation deck so you can stick around and snap some photos after you're done striking poses on the mat.

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  • Comedy
  • Sketch shows
  • Lake View

Bye Bye Liver combines two robust Chicago traditions: comedy and heavy drinking. The show opened over a decade ago for a three-week run, then kept getting extended. A cast of four to six performers portray characters at the fictional "Franks Bar," telling stories that explore the city's robust drinking culture. Each show incorporates interactive audience drinking games, allowing you to sip a cocktail or beer while taking cues from the cast. And if you're up for a nightcap after the performance, you can stick around for the official after party and mingle with the cast.

  • Theater
  • Experimental

For more than 30-years, the Neo-Futurists have been delighting late-night crowds with performances that pack 30 miniature plays into a 60-minute show. The company's signature show is more unpredictable than ever these days, with a handful of compact new plays premiering every week. Within the span of 10 minutes, you may be treated to a poignant monologue about everyday life or an irreverent diatribe delivered by a pantsless member of the cast—all inspired by the experiences of the performers on stage. Always changing and evolving, it's the rare show that truly offers something different everytime you show up to see it.

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  • Comedy

This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.

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