Windy City Smokeout
Photograph: Katie Kauss KDK Creative

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
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Welcome to another weekend! Find the best things to do in Chicago this summer, including movies in parks and drinks at rooftop bars. Enjoy bites from some of the city's best restaurants at EEEEEATSCON, take your pup on a boat cruise or dance to house beats in Jackson Park. Summer festival season is also here, marking the return of favorites like Windy City Smokeout, Miche Fest and West Fest. 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
  • Folk, country and blues
  • United Center

Spend enough time basking in the smell of barbecued meat, the twangy strains of country music and the sweltering heat at Windy City Smokeout and you might feel like you've been transported to Texas. Taking place in a parking lot outside of the United Center, this annual festival brings together some of the nation's most talented pitmasters and a stacked lineup of Nashville-approved musicians. Headliners for this year's edition of the four-day fest include country stars Carrie Underwood, Cody Johnson, Parker McCollum and Thomas Rhett. Come for the delicious smoked meats and stick around for the music.

  • Things to do
  • Bronzeville/Oakland

One of Chicago’s premier celebrations of Latin music will bring together some of the biggest names in the industry across a variety of genres, including reggaeton, salsa, bachata, banda and rock. The two-day fest boasts a lineup of exciting acts, such as Kali Uchis, Junior H, Los Angeles Azules, Sante Fe Klan and more, plus delicious local eateries, talented artists, a full carnival experience and plenty of micheladas.

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  • Things to do
  • Festivals

The Southport Corridor hosts its annual two-day art festival, bringing together a variety of artists and local vendors near neighborhood landmarks like the Music Box Theatre. Guests can peruse pieces, shop at Southport Avenue stores, take kids to an area packed with interactive games or sit down on a patio to enjoy food and drink specials throughout the weekend. All proceeds benefit the Southport Neighbors Association.

  • Things to do
  • Festivals
  • Lincoln Square

This midsummer block party staple brings alt-country, folk and Americana jams—plus craft brews and snacks from local food vendors—to Lincoln Square. Admission is free, but consider tossing in a donation to benefit small business workshops, community efforts and scholarship programs at the Old Town School of Folk Music. 

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  • Music
  • Woodlawn

Local music collective the Chosen Few DJs takes over Jackson Park for a day of house sets from Wayne Williams, Jesse Saunders, Tony Hatchett, Alan King, Andre Hatchett, Terry Hunter, Mike Dunn and special guests. Stop by to watch a crowd of people dancing to the beat, or jump into the fray and show off your moves.

  • Things to do
  • Festivals
  • River West/West Town

West Town's rollicking street festival returns to Chicago Avenue for three days of music, food and shopping from local vendors. Empty Bottle Presents will curate West Fest's musical lineup, and you can also catch jockeys spinning vinyl on the Bass By the Pound DJ Stage. Plus, browse tons of local vendors and don't miss the Pet Fest area, which features charming attractions like a dog obstacle course and pet painting.

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  • Things to do
  • Festivals
  • Jefferson Park

If you love classic rock, skip Lollapalooza and head to Jefferson Park for a community festival that looks to the past with performances from local cover bands. You'll also find food from neighborhood vendors and a dedicated kids zone where families can hang out and boogie with the little ones.  

  • Things to do
  • Festivals
  • Edgewater

Show up to St. Andrew's Greek Orthodox Church in Edgewater to experience "philoxenia" (Greek hospitality) at this annual festival, where chicken, gyros, pork souvlaki and pastitsio (Greek lasagna) are on the menu all weekend long. Stick around for live Greek music and hits from DJ Yianni, as well as fun and games for kids.

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  • Things to do
  • Festivals

Gaze at neighborhood gardens during this self-guided tour of green spaces around the neighborhood, showcasing the efforts of residents with green thumbs. You can download a map online and make your way through Bucktown gardens—some will even host live music and visual artists creating work throughout the day.

  • Things to do
  • River West/West Town

Infatuation is bringing back EEEEEATSCON, the two-day food festival at the Salt Shed featuring some of the city’s best restaurants plus appearances by celebrities like Chrissy Teigen, Common and Chance the Rapper. Participating eateries include 3 Little Pigs, 312 Fish Market, Lilac Tiger, Diego, Soul & Smoke and more.

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  • Things to do

Calling all Godzilla fans and kaiju enthusiasts! This three-day convention dives into everything related to your favorite giant Japanese monster. Enjoy exclusive movie screenings, talks with industry experts and meet the famous creators behind the films. Attractions will include panels, a Mecha-G arcade, vendors selling rare and exclusive merch, workshops, cosplay contests and more.

  • Things to do
  • United Center

Windup Watch Fair returns to Chicago for a third year. The three-day-long shopping event invites both seasoned collectors and first-time buyers alike to come shop and talk watches. Over 40 brands will be on site; admission is free.

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  • Things to do

The Big Ten Conference now encompasses 18 teams, so expect to see plenty of sports fans (and their respective mascots) at this 10K (or 5K) race. Participants get to pick a Big Ten school to represent before running through the course, where a tailgate party is waiting just across the finish line.

  • Things to do
  • Loop

Mercury Cruises’ beloved Canine Cruise is back for another season. Bring your four-legged BFF for a 90-minute ride across the Chicago River and Lake Michigan, featuring lively narration on the city's rich history and architectural marvels with dog-friendly highlights, such as dog parks, fire hydrants and dining hotspots. The tour offers unparalleled views of the city’s skyline and countless photo ops both for dogs and owners alike.

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  • Music
  • Hyde Park

Catch live outdoor jazz performances on the first Friday of every month this summer as part of Jazz in the Court, a free concert series hosted at Harper Court in Hyde Park. Performers this year include Hurricane Reggae Band (June 7), Tony Carpenter (July 5), Thaddeus Tukes (August 2) and Corey Wilkes (September 6).

  • Lincoln Park

Steppenwolf concludes its 48th season with the world premiere of Little Bear Ridge Road, an intimate drama by MacArthur Fellow Samuel D. Hunter, directed by Tony Award winner Joe Mantello. The plot follows two estranged family members reuniting in rural Idaho to sort the mess left behind after a troubled father's passing. As the pair’s relationship begins anew, the two reluctant Fernsbys start to understand the joys and perils of letting someone else into your own story, even if only for a moment.

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  • 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.

  • Movies

From June through September this year, dozens of movies will screen in parks all over Chicago as part of the city's annual Movies in the Parks program. From recent blockbusters like Barbie and Wonka to classics like The Princess Bride and Space Jam, you're sure to find good something to watch (for free!) beneath the stars this summer. Screenings typically begin at 8:30pm, or dusk, each evening. Take a look at the full list of movies and participating parks.

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  • Things to do
  • Loop

Sundays on State—which shuts down a strip of State Street spanning from Adams to Lake Streets for activations, performances, food and shopping—brings thousands of visitors downtown to check out everything from outdoor dining and browsing opportunities to pop-up karaoke and barre fitness classes. The event returns on two Sundays this year by popular demand. For a full schedule of vendors and events, check out Chicago Loop Alliance's website.

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  • Things to do
  • Loop

Based on the family-favorite board game, this immersive and interactive experience puts guests into the roles of beloved CLUE characters as they try to solve the murder of estate owner Boden "Boddy" Black. The mystery starts at Block 37, where detectives are greeted by the Butler before being sent on their way to gather clues from popular Chicago sites and shops. You’ll be tasked with finding long-lost antiques and figuring out who did it, where and with what.

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  • Ukrainian Village

Sportsman's Club's backyard BBQ series is back for another year, bringing local restaurants to the bar's patio to cook a meal that's usually paired with a beverage. For the uninitiated, the takeovers are first-come, first-served, with the featured chef holding court over the bar's grill and menu. Food is priced a la carte. Check out the full lineup here and start planning your Sunday afternoons accordingly.

 

  • 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
  • Hyde Park

Check out all sorts of cool trinkets, wares and eats at this indoor market highlighting artisan makers from Chicago’s South Side. Taking place on the second floor of the Promontory, the family-friendly event will feature new and returning vendors, a cocktail bar, lounge areas and tunes by DJ Sean Alvarez of We Love Soul.

  • 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.

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  • 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.

  • 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.

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

  • 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

One of Navy Pier’s newest attractions transports 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

The largest and most immersive touring Titanic exhibition has come 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.

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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.

  • 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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