Chicago’s greenery isn’t the only thing in full bloom this May. From can’t-miss theater and groundbreaking exhibitions to street festivals, art fairs, and spring markets, the city is bursting with energy and inspiration. Whether you’re planning a Mother’s Day outing, looking for weekend plans, or ready to dive into Chicago’s cultural calendar, these are the 31 best things to do in May in Chicago and the suburbs.
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Lines of Connection: Drawing and Printmaking
Held at the Art Institute, this is the first exhibition ever to focus on the multiple connections between drawing and printmaking, this presentation brings together around 90 works on paper by some of the greatest artists in the Western tradition to uncover their creative process and offer new ways to think about the links between the mediums. Running until June 1, 2025.
HYMN
Two middle-aged Black men explore the loyalties and betrayals of brothers, fathers, and sons in this profound tribute to male friendship. Legendary Chicago director Ron OJ Parson leads a powerhouse team, featuring Chiké Johnson and James Vincent Meredith, in this new play by Olivier Award winner Lolita Chakrabarti.
Frida Kahlo’s Month in Paris: A Friendship with Mary Reynolds
Experience Africa Fashion, a one-of-a-kind exhibition celebrating the dynamic voices transforming African style. With over 180 works, including haute couture, ready-to-wear, and multimedia displays, discover how African designers are shaping global fashion. Check out this exhibit while it’s open through June 29 — tickets are available on the Field Museum website.
Africa Fashion
Drawing upon the Mary Reynolds Collection at the Art Institute and extraordinary Kahlo loans from public and private collections in the US, Mexico, and Europe, the exhibition recounts the legacies of Kahlo and Reynolds as they navigated Surrealism, identity, and cross-cultural exchange on the eve of World War II. See it before it closes on July 13.
Bust
Retta and Reggie are enjoying a quiet evening on the porch when their neighbor is pulled over by the police. Everything goes as you might expect—until the unexpected happens. A recording of the event goes viral, sending everyone into a frenzy. It’s not only hell that breaks loose in this ground-breaking, form-defying, laugh-out-loud new drama from Pulitzer-Prize finalist playwright Zora Howard. Visit Goodman Theatre online for more details.
Myth and Marble: Ancient Roman Sculpture from the Torlonia Collection
Beginning in 2020, a series of exhibitions across Europe have brought selected highlights of the Torlonia Collection to public display. Myth and Marble debuts these masterpieces to a North American audience, presenting a once-in-a-lifetime opportunity to experience these exceptional ancient sculptures and explore the fascinating stories they reveal. This exhibit is already open and runs through June 29.
Spectrum of Spring
The 2025 Spring Flower Show highlights the color families of plants and flowers, and offers a unique design and color scheme. Marvel at the robust color blocking of bulbs such as ‘Delft Blue’ Hyacinth, ‘Red Impression’ Tulip, and ‘Golden Yellow’ Crocus. There are also colorful annuals, including ‘Whimsy Blue’ Nemesia and ‘Color Max Orange Clear’ Viola. Lots of perennial and shrub favorites return as well. Above the flower beds, you will find colorful, flowing baskets of calibrachoa, such as ‘Kabloom Cherry’. Don’t miss this explosion of color — make a free reservation online at the Lincoln Park Conservatory.
The Antiquities
A “brilliantly imagined drama” for anyone whose computer has asked them to prove that they’re a human. Which is to say, everyone. At the Museum of Late Human Antiquities, curators are fiercely committed to bringing a lost civilization to life again: What were humans like? What did they wear, what did they eat, how did they die out? This play gives us a view of the present, analog past, and post-human future.
Andersonville Farmers Market
Want to feel the pulse of the city again and get some local goodies, too? Enjoy one of the city’s first outdoor markets of the season, the Andersonville Farmers Market — held at a new location this year. Join vendors every Wednesday at 3-7pm for anything from local produce and honey to candles and tea, from May 14 until October 22. Check out the Andersonville Farmers Market website for a full list of participating businesses and what else to expect when you shop.
1500 West Winona St.
TeaLula Expands After 17 Years
After 17 years of serving premium loose-leaf teas, TeaLula has expanded its offerings to include a delightful lunch menu featuring homemade soups, fresh salads, and signature sandwiches. Additionally, our Afternoon Tea service, introduced May 2024, continues to provide a refined experience. Please contact TeaLula for additional information about this ongoing service.
May 1-2: CineYouth 2025 Streaming
Celebrating 20 years, CineYouth showcases filmmakers 22 and younger from around the world. Now that the fest has passed, viewers can watch all 2025 youth-led films for free on the CineYouth website. This access is only free until May 4, so check the films out now!
May 2-4: Mexico Fest
Join other Chicagoans for the free Global Connections celebration of Mexico Fest at Navy Pier! Experience an authentic cultural celebration featuring amazing music, dance, performances, art, and more. To find tickets and a full weekend line-up of events, visit Mexico Fest online.
May 3: Pilsen Cinco De Mayo Tequila Crawl
Want to get together with friends and celebrate Cinco De Mayo in the city? Then look no further than the Pilsen Cinco De Mayo Tequila Crawl. Bring your high spirits as you and others crawl through the Pilsen neighborhood from bar to bar to have some Cinco De Mayo fun. The crawl includes eight bars, a free drink at every bar and many more goodies. Tickets are on sale now — and the sooner you buy the cheaper they are — so head over to Pilsen Cinco De Mayo Bar Crawl online for details and purchasing.
May 3: Chicago a cappella’s Cabaret Night Fundraiser
ONE NIGHT ONLY! Our fun-filled tradition comes to The iO Theater in Chicago, where our singers bring you an unforgettable night of solos from the worlds of Broadway, jazz, pop, cabaret, and more, accompanied by Paul Langford. Proceeds from the event support our artistic and educational programs.
May 4: Lakefront Loop 5k
The annual Lakefront Loop 5K, and 250 Yard Kids Dash, will kick off at 8am. The 5K is completely within the Pier’s grounds, and the route will incorporate the Northwestern Medicine Wellness Way fitness trail, as well as the iconic North and South Docks. Want to know the perks? Check out the Lakefront Loop 5k website for more info and registration.
Navy Pier, East Grand Avenue
May 4: 2025 North Shore Jazz and Classical Music Festival
The North Shore Jazz and Classical Music Festival aka “Fun Fest” is an annual free community event, open to the public with live music, games, food, and fun! With the event landing on May 4th, Star Wars fans can expect to see that theme throughout. Register online to join in on the music, food, drinks, raffle, and more. Details on the Midwest Young Artists Conservatory website.
May 4 + 11: For the Record | NoMI Lounge
Unwind at For the Record in NoMI Lounge, where vinyl sets the tone and cocktails shine. Enjoy rotating themed cocktails, exclusive drinks, and the chance to choose a record for the evening’s soundtrack—your perfect Sunday night escape in the heart of the city. Every Sunday from 5-9pm.
May 8: Wine & Design
When wine and art meet you end up with a little something like Wine & Design, a tasting tour held at THE MART — in partnership with Wine Spectator Magazine — from 6-8pm. Enjoy tastings of wine from around the world with savory hors d’oeuvres while you tour the inspiring showrooms on the first floor. For your opportunity to stroll through the iconic Chicago institution, visit THE MART online for registration and more.
222 Merchandise Mart Plaza
May 10: Second Saturdays at the Goodman
Second Saturdays at the Goodman are family-focused intergenerational workshops centered on joy, creativity, and sharing space. Join us each Second Saturday of the month to participate in workshops facilitated by Goodman Teaching Artists as we celebrate creativity and the art of storytelling.
May 11: Mother’s Day Brunch at NoMI Kitchen
Enjoy chef stations with fresh sushi, seasonal salads, roasted tenderloin, and halibut. Sip free-flowing mocktails and juices before indulging in desserts. Kids can enjoy mac & cheese, chicken tenders, and a waffle station. Every mother receives a bouquet and a wax-sealed note with your personalized message.
May 12: Chicago Sings 30 Years of Porchlight
Porchlight Music Theatre presents Chicago Sings 30 Years of Porchlight, Monday, May 12 at 7 p.m., with a 5:30 p.m. reception, at the House of Blues Chicago, 329 N. Dearborn St.
May 15: Evanston Arts & Craft Beverage Crawl
The highlight to this art crawl is the importance of locally-owned businesses, such as the delicious Evanston-made boozy beverages and fun food pairings that guests can enjoy during this three hour fest. While there, see inspiring local artists’ work, some live entertainment and get a goodie bag to top it all off. There are countless vendors and a whole lot of fun in store, check out the Evanston Arts & Craft Beverage Crawl page to find all the details and grab tickets.
May 16: NoMI Garden Maison Marché: Season Opener
Kick off summer at NoMI Garden’s Maison Marché on May 16 from 5-7pm. Enjoy craft cocktails, a garnish wall, sushi, oysters, seasonal bites, desserts, and a live DJ—set against stunning city views. 21+ Only, Cocktail Attire.
May 16-18: Lincoln Park Mayfest
Kick off the festival season in the city with the annual Lincoln Park Mayfest. Attendees can enjoy the sounds of some of Chicago’s best artists, but it’s not just about the music, the new Spring Fine Art Mart will also be a central feature of the event. Plus good food and activities! Head over to Lincoln Park Mayfest for what to know before you go.
May 17-18: Skokie Festival of Cultures
To honor all the cultures represented in Chicagoland, the Skokie Festival of Cultures returns for another triumphant summer. Held at Oakton Park in Skokie, the festival will feature music and dance on stage; interactive cultural booths; children’s games and activity area; the festival’s famous flag display; food and beverage vendors; and much more. What a great opportunity to experience something you may not otherwise — check out the Skokie Festival of Cultures for more information.
May 17-18: Midwest Bonsai Society Spring Show & Sale
Beloved by many, the Midwest Bonsai Society Spring Show & Sale returns to the Chicago Botanic Garden this May. From 9am-5pm, marvel at the flowering bonsai, bonsai on rocks, bonsai trees in various stages of development with interpretation highlighting the caretakers’ intentions. There will be hundreds of bonsai specimens on display and for sale, as well as free demonstrations, lectures and workshops for all levels of bonsai enthusiasts. Register on the Chicago Botanic Garden website.
1000 Lake Cook Rd., Glencoe
May 17-18: Lincoln Roscoe Art + Craft Fair
Returning to Lakeview Roscoe Village on May 17 and 18, this event features art for the home including fabulous paintings, sculptures, and fiber pieces, as well as décor, jewelry and more; all hand made by artists and artisans. Live music all weekend long, festival food and fun art activities for kids hosted by local businesses, make this a fun-filled must attend event! Beer lovers will be happy to see a broad selection of brews and wine curated by Bitter Pops for purchase, hosted by Friends of Lakeview.
Lincoln Avenue From Roscoe to Melrose Street
May 17-18: Chicago Master Singers and Metropolis Symphony “Brahms Requiem”
Experience the Brahms Requiem and Ola Gjeilo’s Dark Night of the Soul with Chicago Master Singers, the Metropolis Symphony Orchestra and vocal soloists Katelyn Lee and Nicholas Miguel. Music Director John C. Hughes conducts.
May 23-25: Belmont-Sheffield Music Fest
The Belmont-Sheffield Music Fest is ringing in its 40th year this summer! Join them in Lakeview for can’t-miss local tribute bands, great eats, strong libations. Check out the artisan vendors, too! Summer fun starts here, visit the Belmont-Sheffield Music Fest website for more info.
3200 N. Sheffield Ave.
May 24: Memorial Day Fireworks at Navy Pier
Navy Pier kicks off their summer fireworks series this month just before Memorial Day — held on May 26. A few days prior, enjoy the colorful splendor of the largest, annual fireworks display in Chicago. Check out the Navy Pier website for details about this free event.
800 E. Grand Ave.
May 24-25: Randolph Street Market Festival
Every year, vendors from around the country come to the Randolph Street Market Festival to sell the best art, antiques and vintage decor, ephemera, vintage and indie designer fashion and jewelry, vinyl, global goods, fancy and fun foods. This European-style flea market festival will not only have goods but live music too! Head down to the West Loop to see what this iconic fest is all about.
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Margaret Smith is a Chicago-based writer and editor with a passion for socio-political storytelling about their community. They are a graduate of Columbia College Chicago.
