31 Best Things to Do in Chicago and the Suburbs This May 2024

Chicago’s greenery isn’t the only thing that flourishes in May. With the warmer weather, the city comes alive with outdoor — and indoor — marketplaces, eateries, performances, exhibits, community events and more. Whether you’re looking for something free to do on the weekend or want to grab tickets to Chicago’s hottest events — we’ve rounded up the best things to do in Chicago and the suburbs this month.

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All Month

Christina Ramberg: A Retrospective

Untitled (Hand), 1971 | Photo courtesy of the Art Institute of Chicago

Christina Ramberg was an influential member of Chicago’s contemporary art scene in the ’70s and ’80s. While best known for her paintings of fragmented female bodies, throughout her career she vacillated between the depiction of various figural elements while also creating abstracted forms that emphasize structure and surface. View her exhibit at the Art Institute now through August 11 — reserve your chance to see it by visiting Christina Ramberg: A Retrospective online.

111 S. Michigan Ave.

Hershey Felder as Monsieur Chopin – A Play with Music at Writers Theatre

In a tour de force performance, virtuoso actor and pianist Hershey Felder brings to life the romantic story and music of Fryderyk Chopin, the man once called the “Poet of the Piano.” Find more details about the performance — running now through May 12 — and secure your tickets by visiting the Writers Theatre website.

325 Tudor Court

Spring Flower Show: What’s In A Name?

This year’s Spring Flower Show at the Garfield Conservatory covers the history and science of botanical nomenclature alongside a beautiful flower show full of gorgeous flora. Over the years, through plant names, we have created ways of communicating history, culture and identity. Stop by for the beautiful blooms, and stay for the history lesson. Make your reservation online by visiting Garfield Conservatory, now through May 12.

300 North Central Park Ave.

The Choir of Man

Now through May 26th, catch The Choir of Men — straight from London’s West End — at the Apollo Theater Chicago. Dubbed an “uplifting celebration of community and friendship where everyone is welcome” and “a theater experience unlike any before” this show is one for lovers of music of any kind. Set in the “best pub in the world,” a cast of nine men combine “hair raising harmonies, foot stomping singalongs, world class tap dance, and poetic meditations on the power of community.” Grab your tickets now, visit The Choir of Men for more.

2550 N. Lincoln Ave.

007 Science: Inventing the World of James Bond

Through October 27, The Museum of Science and Industry wants to welcome guests to the first-ever “official exhibition to focus on the science and technology behind the world’s longest-running movie franchise” — 007 Science: Inventing the World of James Bond. From iconic cars and gadgets to props from the James Bond film series, this exhibit has it all. Go behind the scenes to learn how the production team pulled off the marvel that is the James Bond series. All exhibit logistics and tickets can be found online at 007 Science: Inventing the World of James Bond

5700 South Lake Shore Dr.

Navy Pier Flyover

Discover the beauty and awe of Chicago with Flyover — the latest attraction on Navy Pier that takes guests on a virtual, up-close tour of the city. The immersive journey connects users with the city by soaring over iconic locations and diving into authentic stories, all from the comfort of Navy Pier. Sound like your kind of adventure? Get your tickets now by visiting Navy Pier Flyover online.

600 E. Grand Ave.

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, now in its 15th year. Join vendors up on Catalpa Avenue between Clark Street and Ashland Avenue every Wednesday at 3-7pm for anything from local produce and honey to candles and tea, from May 15 until October 23. The vendors rotate per week, check out the Andersonville Farmers Market website for a full list of participating businesses and what else to expect when you shop.

Unseen Oceans

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Open now until next January at the Field Museum, a new exhibit will showcase the awe-inspiring, unimaginable vastness of the oceans. Guests will be able to explore everything from the ocean’s “white-capped waves to their inky depths” and a lot in between. The exhibit includes screens to watch life-sized creatures, tanks full of real ocean dwellers, immersive experiences and more. Visit the Field Museum to reserve your spot.

1400 S. Dusable Lake Shore Dr.

May 2: Wine & Design: A Tasting Tour at THE MART

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 3-4: Middle School Expedition at the Reagan Boyhood Home

This May 3-4, step into the world of President Ronald Reagan’s youth at his Boyhood Home in Dixon, Illinois, with the Young America’s Foundation’s inspiring Middle School Expedition. For $30, students in grades 6-8 will tackle the “Reagan Resilience Challenge,” a series of interactive activities designed to teach pivotal values. Visit Middle School Expedition online for details.

May 4: Enchanting Seascape: Elmhurst Symphony Orchestra Presents La Mer

The Elmhurst Symphony Association (ESA)  announces its upcoming concert, La Mer, set to enchant audiences on Saturday, May 4 at 7:00pm. The performance will take place at the Elmhurst Christian Reformed Church (ECRC) in Elmhurst. Head over to Elmhurst Symphony Orchestra online for tickets and details.

149 W. Brush Hill Rd., Elmhurst

May 4: 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. Dress for the occasion and 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 nine bars, a free drink at every bar and many more holiday goodies. Tickets are on sale now — and the sooner you buy the cheaper they are — so head over to Pilsen Cinco De Mayo Tequila Crawl online for details and purchasing.

May 4: Paddle for a Purpose

Join others at Sure Shot Pickleball for “Paddle for a Purpose” fundraiser featuring a pickleball tournament, music, food and prizes! Visit the Paddle for a Purpose website for all the details you need.

Sure Shot Pickleball, 2244 Corporate Ln., Naperville

May 5: The Lakefront Loop 5K

In support of Navy Pier’s non-profit mission to “welcome all and provide dynamic arts and cultural experiences for our community,” they are hosting The Lakefront Loop — a 5K completely within the Pier’s grounds. 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 Navy Pier website, where registration is also available.

800 E. Grand Ave.

May 5: Northshore Jazz & Classical Music Festival

In the summertime, nothing beats a family outing where everyone can find something to enjoy — if you venture to the Northshore Jazz & Classical Music Festival you just might find that and more! For the kids there are carnival rides, a cake walk, games and more. For the adults, enjoy a variety of food trucks against the backdrop of some stellar live jazz and classical music. Families can enjoy the fun from 12:30-6:45pm, see the rest of the details on the Midwest Young Artists website — the sponsors of the event.

MYAC Center, 878 Lyster Rd., Highwood

May 9-11: 7NMS | Marjani Forté-Saunders and Everett Saunders, Prophet: The Order of the Lyricist

A multi-genre storytelling project about the life journey of a lyricist — Prophet: The Order of the Lyricist — illuminates the distinctive practices, systems, philosophies and political ideologies that have shaped hip-hop’s emcees and lyricists. MCA’s presentation of Prophet, represents the culmination of a year of relationship-building with organizations, artists and archives.

220 E Chicago Ave.

May 11: Steppenwolf Theatre Company Gala 2024

Steppenwolf’s Ensemble and Board of Trustees invites guests to a “magical night celebrating Chicago’s most-storied company.” Join Steppenwolf artists and leaders from their civic and business community for cocktails, dancing and a gourmet seated dinner. Funds raised at the event are vital for supporting the artistic home for Steppenwolf’s Ensemble, as they strive to “bring bold and innovative theatrical experiences to the stage, and creates educational programs that reach thousands of teens throughout the Chicago region.” Join them for a night full of artists, DJ, and an after-hours lounge. Attire is fun, urban chic. Details are on the Steppenwolf Theatre Company Gala site.

1200 W. 35th St.

May 11: Mother’s Day Sip & Paint

This Mother’s Day, give your mom an afternoon of fun at Casa Arte with their Sip & Paint event. Participants and their moms can let their creativity flow as you sip and paint together. Enjoy photo ops included in your ticket for lasting memories. This event is BYOB and mixers are available for purchase onsite. Don’t miss this unique opportunity to celebrate your mom with a creative twist. Visit Mother’s Day Sip & Paint online for details.

2401 W. North Ave.

May 12: Mother’s Day Brunch at NoMI

Spoil Mom with the ultimate surprise at NoMI’s Mother’s Day Brunch, featuring four-course prix-fixe brunch, monogrammed menus and a personalized letter from you. Visit NoMI online for all the details.

NoMI, 800 Michigan Ave.

May 14: 22nd Annual Heroes Breakfast

For over 20 years, the American Red Cross of Greater Chicago “has honored individuals and groups for acts of immense bravery, dedication and service to the community” at their annual Heroes Breakfast. The Red Cross welcomes you to join them as they pay honor to our brave community members — from youth advocates to medical personnel and more. The event is 7:30-10am, held at the Chicago Hilton. Visit the Heroes Breakfast page for details and registration.

720 S. Michigan Ave.

May 16: 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.

The Main-Dempster Mile, 900 Chicago Ave., Evanston, Illinois

May 17-19: Chicago Mayfest

Kick off the festival season in the city with the 27th annual Chicago Mayfest, held in Lincoln Park. Attendees can enjoy the sounds of some of Chicago’s best artists as they play across two stages, but it’s not just about the music, the Armitage Art Show will also be a central feature of the event. Head over to Chicago Mayfest for what to know before you go.

1000 W. Armitage Ave.

May 18: Argyle Asian American and Native Hawaiian/Pacific Islander (AANHPI) Block Party

Argyle Street is known as “the center of Chicago’s premiere Southeast Asian business and entertainment district.” And this year — in honor of Asian American and Native Hawaiian/Pacific Islander (AANHPI) Heritage Month — they will host their inaugural Argyle AANHPI Block Party. The event will bring together “vendors, artists, cultural organizations and people together in celebration of the Argyle corridor and the wide array of diversity that exists within Chicago’s AANHPI community.” More information can be found on the Argyle AANHPI Block Party website.

1132-34 W. Argyle St.

May 18: Deem Symposium | Designing for Dignity 02: A Convening of Possibilities

Photo by Brian Crawford

Deem presents its second live symposium: Designing for Dignity 02: A Convening of Possibilities. Deem will expand on the guiding premise of dignity as the intrinsic lens for liberatory design practices with two days of presentations, conversations, interactive workshops and on-site experiences happening at the MCA and throughout Chicago. Tickets and more can be found on the Deem Symposium website.

220 E. Chicago Ave.

May 18-19: Festival of Cultures

To honor all the cultures represented in Chicagoland — known for being a melting pot — 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; food and beverage vendors; interactive cultural booths; children’s game and activity area; the festival’s famous flag display and much more. What a great opportunity to experience something you may not otherwise — check out the Skokie Festival of Cultures for more information.

4701 Oakton St., Skokie

May 18-19: 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 and suiseki — which is the Japanese art of stones. 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 18-19: Lincoln Roscoe Art + Craft Fair

This event will feature a number of different creative projects for sale including: fabulous paintings, sculptures, and fiber pieces, as well as décor, jewelry and more; all hand made by artists and artisans. Live music will also be played all weekend long. Expect to enjoy festival food and fun art activities for kids, hosted by local businesses. 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. Want to know more? Check out the Lakeview Roscoe Village website.

Lincoln Ave., from Roscoe to School St.

May 19: GLI Charity Exotic Car Show

Join Glenview’s favorite spring festival! Enjoy rare cars, kids’ activities, food, drinks, and live music while supporting fallen first responders’ families. Details, including what to expect, and more can be found online at GLI Charity Exotic Car Show.

May 24-26: Mole De Mayo Festival

If you’ve got a taste for Mexican food, then you’re no stranger to the delicious sauce used across the cuisine: mole. Each person who makes this traditional sauce has their own flare, which is how the Mole de Mayo Festival was born. Enjoy sampling food from over 20 “popular festival food vendors, each bringing their own savory, sweet or spicy version of mole.” After you’ve gotten your fill, vote for who will be the 2023 People’s Choice and Best Mole winner. A full list of details, locations and everything you need to know can be found on the Mole de Mayo website.

May 24-26: Belmont-Sheffield Music Fest

The Belmont-Sheffield Music Fest is ringing in its 39th year this summer, and with all that success under their belt, we doubt they will disappoint. Join them in Lakeview for can’t-miss local tribute bands, great eats, strong libations and, best of all, see your community members entertain with music acts, DJing and other performances. The summer brings us all out into the city, so enjoy yourself while you’re at it! Got questions? Peruse the Belmont-Sheffield Music Fest website for more.

3200 N. Sheffield Ave.

May 25: Memorial Day Fireworks at Navy Pier

Weekend 101: Memorial Day Weekend 2019

Navy Pier kicks off their summer fireworks series this month just before Memorial Day — held on May 27. 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.

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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.

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