May 2024 events calendar for Chicago

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.

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. 

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.

After a wreath is laid at the eternal flame in Daley Plaza at 11am in remembrance of those who died serving in the U.S. armed services, Chicago's annual Memorial Day Parade marches down State Street (from Lake to Van Buren streets) beginning at noon. Crowds line the street waving flags and paying their respects as part of this Chicago tradition, which dates all the way back to 1870.

Wrigley Field-adjacent plaza Gallagher Way is once again showing free outdoor movie screenings this summer. Admission is free and attendees are welcome to bring their own food, enjoy on-site concessions or snag a meal from nearby restaurants like Big Star and Smoke Daddy. VIP seating is also available for $33—check out the Gallagher Way website for more details. Gates open at 6pm for each screening and the movies start at 7:30pm.

• May 15: The Super Mario Bros Movie
• May 29: High School Musical 2
• June 12: Wonka
• June 26: Barbie
• July 10: School of Rock
• July 17: Angels in the Outfield
• July 31: Soul
• August 14: Harry Potter and the Sorcerer's Stone
• August 28: TBA
• September 11: Twilight

Get an inside look at eight Frank Lloyd Wright-designed buildings—including private residences normally closed off to the public—as part of this one-day touring event run by the iconic architect's trust, during which visitors will get to walk around the structures and hear detailed tours about their history. Take a peek inside everything from the Robie House in Hyde Park to the gorgeous homes lining Oak Park streets, and learn about one of America's most cherished architects. 

This annual fest and conference celebrating the iconic dance music genre born in Chicago brings a full day of DJ sets to Millennium Park. Acts this year include Wayne Williams, Alan King, Farley Jackmaster Funk, Tony Touch, DJ Slugo and more. The live music will be preceded by and open house and panel discussions touching on key House topics at the Chicago Cultural Center. For a full list of programming, visit the DCASE Chicago House Music Festival and Conference website.

Kick off the start of summer festival season at Do Division, the street shindig with live music booked by Empty Bottle and Subterranean in West Town. Catch performances at two stages—including acts like Divino Niño, Arm's Length, Susto and Avey Tare—and check out food trucks, a fashion show, vendors for shopping and a Family Fun Fest area with kids activities, among other attractions.

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. 

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. In this two-day fest, 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.

Renegade Craft Fair's flagship event returns to Andersonville, taking over a stretch of Clark Street spanning from Bryn Mawr to Edgewater Avenue. Attendees will be able to shop the handmade wares of more than 250 vendor booths, selling everything from candles and screenprints to jewelry and pottery. The fair also boasts food and drink from local restaurants, so you won't have to go hungry (or thirsty) while you shop.

Say a hearty hello to summer at Mayfest, the annual street party in Lincoln Park that's outfitted with the usual selection of local vendors, tasty food, cover bands and ice-cold beverages. This year, the event will feature the Armitage Art Show, letting attendees experience Chicago’s top artists as they showcase and sell their works and present interactive art demonstrations.

The street in front of St. George Greek Orthodox Church hosts three days of gyros, spicy feta spread, dancing, traditional music and more during Lincoln Park's annual celebration of Hellenic culture. Show up to feast on Greek delicacies, shop for gifts at the craft fair or catch some live music.

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.

Taking place on Lincoln Avenue between Roscoe and School Streets, this two-day event will present more than 75 vendors selling handmade art—including paintings, sculptures and fiber pieces—as well as jewelry and decor. The weekend will also have live music, festival food and a selection of brews for purchase curated by Bitter Pops.

This inaugural Margarita Festival in Pilsen promises three days of tasty Latin bites, live music, local art and (of course) refreshing cocktails. You’ll have over 15 varieties of margs to try, from classic to unique options, and be able to browse goods from local merchants. The entertainment lineup boasts cover bands Fuze (Santana), Revelacion de Amor (Mana) and local DJs.

Documentaries, dramas and shorts make up the 27th edition of the Asian American Showcase, which highlights new works by established and emerging Asian American filmmakers. This year's lineup includes Sean Wang's Sundance Award winner Dìdi, Ashima by director Kenji Tsukamoto, Smoking Tigers by So Young Shelly Yo and many others.

Wrigley Field is a baseball mecca but from May 10-13, you’ll be able to play a round of golf inside the stadium. The exclusive experience will let guests hit tee shots from the upper deck down to custom greens on the field below. Once you’re finished, head to the clubhouse for music, food and beer.

Rooftop Cinema Club, the open-air theater perched atop The Emily Hotel, is back for another season. Guests can catch showings of hand-picked classics, cult films and recent releases while also enjoying sweeping views of the skyline and craft beverages. It’s the perfect summer cinema experience. Check the official website for the full schedule and lineup.

Looking for free concerts near Chicago? Hop on the Blue Line to Rosemont's Parkway Bank Park for Thursday night performances—with a few holiday and weekend dates sprinkled through the summer—from classic rock cover bands like Dancing Queen (ABBA), Ticket to the Moon (Electric Light Orchestra) and Elton Rohn (Elton John, obviously), complete with a fireworks show at the end of the night. Beverage tents will be located on site, but we won't fault you if you prefer to pre-game with a fishbowl-sized spiked punch from nearby Sugar Factory. For a full schedule of shows, visit the Parkway Bank Park website. 

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. 

Embarc—an organization that provides provides community-driven, experienced-based learning opportunities to low-income youth—is hosting its annual gala on May 16 at The Geraghty. Enjoy an evening of performances, curated experiences and gourmet food and drinks while helping to raise money to support nearly 4,000 students and 200 teachers.

The Lincoln Park Chamber of Commerce hosts the neighborhood's Uncorked Wine Stroll, an evening showcasing Lincoln Park businesses. With a dozen stops along Armitage and Halsted, light bites and snacks and—of course—lots of wine, there’s no better way to get to know the neighborhood. Cobble together a group of five or more to save $5 per ticket!

Now in its 19th year, the Andersonville Wine Walk, which benefits the Andersonville Chamber of Commerce, sees businesses throughout the neighborhood turn into wine destinations. You'll be able to sip, tour and shop your way through two wine routes curated by In Fine Spirits. Attendees will receive a commemorative wine tasting glass and a card highlighting each wine before embarking.

Curious Theatre Branch's Rhinoceros Theatre Festival, which bills itself as Chicago's longest-running fringe festival, returns for its 35th outing with a slate of new theater, music performances, art and more. Visit rhinofest.com for the complete schedule.

Get ready to hunt for some new (and old) treasures! The beloved Randolph Street Market Festival is back for its 21st year with two days of curated, European-style vintage and antique shopping. Browse wares from hundreds of vendors, or grab a cocktail and bite to eat from local restaurants while tapping your toes to live music. 

Join BiXi Beer in celebrating Asian & Pacific American Heritage Month with a chef’s charity dinner benefitting Advancing Justice Chicago. The evening will feature courses by Margaret Pak (Thattu), Thai Dang (HaiSous), Won Kim (Kimski), Bo Fowler (BiXi) and Sherrie Tan (Sweet Mandy B’s), along with curated cocktail pairings. Tickets are $175.

The Chicago Critics Film Association throws an annual film fest, giving the public a chance to see buzzed-about unreleased films and overlooked movies that deserve to be seen on the big screen. This year's lineup includes a 30th anniversary screening of Gillian Armstrong's Little Women, Chicago-made Sundance Film Festival breakout Ghostlight and The Fabulous Fleischer Cartoons Restored, a series of animated shorts originally produced by Max Fleischer between 1919-1942. Check out the complete festival lineup on the Chicago Critics Film Festival website.

Chicago Writers’ Bloc puts on this festival featuring staged readings of five new plays and five new musicals from local playwrights, lyricists and composers. The works range from comedy and drama to documentary theatre, including Hearts in the Wood, Hell is Canceled and No Kind of Hero.

Winter is almost over and the Garfield Park Conservatory is here to usher in warmer days with its Spring Flower Show. Make a reservation to explore this year's show, "What's in a Name?" which explains the history and science of botanical nomenclature. You'll find spring bulbs like Tulipa ‘Rococo’, Lilium ‘Josephine,’ Viola ‘Matrix Yellow’ and Anemone ‘Giant Blue Poppy.’ The show only sticks around through Mother's Day weekend, so book your visit soon!

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.

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.

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.

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.

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.

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.

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.

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.

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.

Chicago Gamespace, a video game museum and gallery, opens a new exhibit that explores the unique and ephemeral history of vector (line) graphics in contrast to the dominant raster (pixel) visual displays that reign today. Notable games like Asteroids, Battlezone and Star Wars will be highlighted, as well as a recently-preserved emulation of Moonlander.

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.

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.

Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. The Doane Observatory is also home to the largest public telescope in the area, and gathers 7,000 times more light than the human eye. Every Wednesday, the Adler stays open late from 4pm-10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.

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.