May in Chicago is a time of renewal, celebration, and reconnection. As the city shakes off the last signs of winter, parks come alive with color, patios reopen, and the streets buzz with energy. It’s the perfect month to explore everything Chicago has to offer—from world-class music festivals and outdoor art shows to neighborhood street fairs, family-friendly outings, and culinary events that spotlight the city’s rich food scene. Whether you're a music enthusiast, culture lover, or just looking to enjoy the fresh air, May invites you to dive in.
Keep reading for a roundup of the best events happening across Chicago this month—you won’t want to miss them.
🎡 🎪 Festival Season Is Here
Get ready to stroll through street fairs, dance to live music in city parks, and indulge in everything from craft beer to chocolate-dipped everything. May kicks off Chicago’s iconic festival season with something happening nearly every weekend. Whether you're looking to celebrate Latin culture at Sueños Festival, sip your way through Illinois Craft Beer Week, or explore art in Lakeview or Andersonville, there’s a festival with your name on it.
Sueños Music Festival
May 24–25 | Grant Park
Experience the vibrant rhythms of Latin music at the Sueños Music Festival, Chicago's premier Latin music event. This year's lineup boasts international superstars including Shakira, Don Omar, and Peso Pluma, alongside a diverse array of artists such as Grupo Frontera, Arcángel, El Alfa, and Jhayco .
Lincoln Roscoe Art + Craft Fair
May 17–18 | Lakeview
Explore a diverse range of handmade art, jewelry, and crafts from local artisans in the heart of Lakeview.
Illinois Craft Beer Week
May 9–16 | Various Locations Across Chicago
This annual event showcases the state's vibrant beer culture through a series of tastings, tap takeovers, and special releases across Chicago's breweries and taprooms.The week kicks off with the flagship event, Beer Under Glass, on May 9 at the Millennium Park Harris Theater Rooftop Terrace. Attendees can sample from over 200 craft beers poured by more than 80 Illinois breweries, all set against the stunning backdrop of Chicago's skyline
Renegade Craft Fair
May 17–18 | Andersonville
This curated marketplace features independent makers and designers, offering everything from ceramics to textiles.
🎶 🎷Music & Concerts
May in Chicago is a symphony of sounds, offering a diverse lineup of concerts that cater to every musical taste. From legendary artists gracing iconic venues to emerging talents making their mark, the city's music scene is alive and thriving this month. Whether you're into rock, pop, classical, or indie, there's a performance waiting to captivate you.
The Weeknd – After Hours til Dawn Tour
May 30–31 | Soldier Field
Experience The Weeknd's dynamic show featuring hits from his latest album, with special guest Playboi Carti.
Paul Simon – A Quiet Celebration Tour
May 21–24 | Symphony Center Orchestra Hall
The legendary Paul Simon returns to the stage, offering intimate performances that showcase his timeless songwriting.
Ichiko Aoba
May 7 | Thalia Hall
Experience the ethereal sounds of Japanese folk artist Ichiko Aoba in the intimate setting of Thalia Hall.
Harry Potter and The Chamber of Secrets in Concert
May 16–18 | Symphony Center Orchestra Hall
Relive the magic of the second Harry Potter film with a live orchestra performing John Williams' iconic score alongside the movie.
Joe Pug with Courtney Hartman
May 24 | Old Town School of Folk Music
Singer-songwriter Joe Pug teams up with Courtney Hartman for an evening of heartfelt folk music.
Porter Robinson
May 17 | Radius Chicago
Electronic music maestro Porter Robinson brings his immersive live show to Chicago, blending visuals and soundscapes.
🎭 Theatre & Performing Arts
May in Chicago is a vibrant time for theatre enthusiasts, offering a diverse array of performances ranging from Broadway hits to avant-garde productions. Whether you're drawn to classic musicals, contemporary dramas, or experimental works, the city's stages are alive with storytelling that captivates and inspires.
Hadestown
May 6–18 | CIBC Theatre
Experience the Tony Award-winning musical that intertwines the tales of Orpheus and Eurydice with a hauntingly beautiful score.
Titanique
May 6–31 | Broadway Playhouse
A hilarious musical parody that combines the story of Titanic with the music of Celine Dion.
Titanic the Musical
May 7–31 | Marriott Theatre
This stunning production details the Titanic's final days through the eyes of its passengers and staff.
42 Balloons
May 24–Jun 29 | Chicago Shakespeare Theater
A soaringly original musical inspired by the true story of "Lawnchair Larry," who took flight with 42 weather balloons.
🍡🌭 Food & Drink Festivals
May in Chicago is a culinary celebration, offering a diverse array of food and drink festivals that showcase the city's rich gastronomic scene. From international flavors to local brews, these events provide an opportunity to indulge in delicious offerings while enjoying the vibrant atmosphere of the city.
Mole de Mayo Festival
May 24–26 | Pilsen
Experience a unique street festival celebrating Mexican culture with a mole sauce cook-off, live music, art, and even lucha libre wrestling.
Chicago Maifest
May 16–18 | Lincoln Square
Kick off the festival season with this traditional German-American spring festival featuring beer gardens, live music, dancing, and German food.
Wine Tasting in Lilacia Park
May 17 | Lombard
Enjoy a selection of wines in the beautiful setting of Lilacia Park, accompanied by live music and the park's blooming lilacs.
Chocolate Fest
May 16–18 | Long Grove
Indulge your sweet tooth at this festival dedicated to all things chocolate, featuring a variety of chocolate vendors, live music, and family activities.
🌆 Wrapping Up: Make the Most of May in Chicago
As spring fully blooms, May in Chicago offers the perfect backdrop to explore the city’s neighborhoods, culture, and community spirit. Whether you're grooving at a lakefront music festival, discovering new flavors at a food truck rally, catching a Broadway-caliber show, or admiring local art at a street fair, there's no shortage of ways to make memories this month.
Don’t let the season pass you by—mark your calendar, grab your friends, and step into the best that Chicago has to offer this May.
📩 Want updates on Chicago happenings, local real estate, and hidden gems? Join our newsletter or follow us on Instagram @kd_homeschicago to stay in the loop.