Chicago’s landscape isn’t the only thing hitting its stride this May. The city is alive with can’t-miss theater, ambitious exhibitions, street festivals, art fairs, and spring markets that stretch from downtown to the suburbs. Whether you’re planning a Mother’s Day outing, Memorial Day weekend, or just looking for a reason to stay out a little longer, these 31 standout events capture Chicago at its best right now.
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All Month
Korean National Treasures: 2,000 Years of Art
From 6th-century gilt bronze Buddhist sculpture through Joseon dynasty painting and white porcelain and contemporary paintings of the late 20th century, the works of art in this exhibition demonstrate the artistic legacy produced on the Korean peninsula over millennia. See it for yourself, now through July 5, 2026 at the Art Institute of Chicago — a 2026 Make It Better Foundation Philanthropy Award Winner.
One Hope United
May is National Foster Care Awareness Month, and One Hope United is partnering with restaurants throughout Chicagoland to benefit foster care youth. Each restaurant will have a featured item with $1 being donated to One Hope United. Get involved by dining at participating restaurants throughout the month of May.
Spring Flower Show: Showers of Flowers
Step into Showers of Flowers, the 2026 spring flower show at the Garfield Park Conservatory. The exhibition highlights more than 80 hanging baskets that showcase creative vertical possibilities for home gardeners. Displays feature trailing vines such as ivy and sweet potato, bushy asparagus ferns, and colorful blooms including pansies, petunia, and calibrachoa.
Guests can wander beneath cascading florals while taking in ground plantings of seasonal favorites such as daffodils, tulips, lupines, cymbidium orchids, astilbe, snapdragons, and ranunculus, all set against a backdrop of azaleas, camellias, and hydrangea. The exhibition is on view through May 10.
Crafting Characters: The Costumes of Paul Tazewell
Now through September 7, to witness the craftsmanship and genius of costume designer Paul Tazewell, look no further than Chicago’s Griffin Museum of Science and Industry. This exhibit is “deeply inspiring, immersive, and invites you into the world of Paul Tazewell’s creative journey — tracing the artistry, imagination and craftsmanship that inspired the creation of iconic costumes from the blockbuster sensation Wicked to Broadway’s Hamilton to Steven Spielberg’s West Side Story and more. Displays of his masterpieces combined with his narration and video, photos and sketches draw back the curtain to show how imagination becomes reality.” For tickets and more information, visit Crafting Characters: The Costumes of Paul Tazewell.
Matisse’s Jazz: Rhythms in Color
Jazz, one of the most important artist books from the 20th century, includes 20 color plates and text by Matisse. This exhibition marks the first time Jazz has been on view in its entirety since acquisition, and includes more than 50 works by Matisse from across the Art Institute’s collection. See this exhibit through June 1, 2026.
Theater of the Mind
Theater of the Mind, co-created by Academy, Grammy, and Tony Award–winning artist David Byrne and writer and investor Mala Gaonkar and directed by Andrew Scoville, is an immersive theatrical experience at Goodman Theatre that unfolds as a guided journey through a series of sensory environments. In groups of 16, audiences move through interconnected rooms over 75 minutes, engaging sight, sound, taste, and touch in experiences inspired by neuroscience that challenge how we perceive and construct reality. The run has been extended through July 12.
Learn more about Theater of the Mind in our interview with David Byrne.
Andersonville Farmers Market
Want to enjoy a day outside and get some local goodies? Visit one of the city’s first outdoor markets of the season, the Andersonville Farmers Market. Join vendors every Wednesday at 3-7pm and browse for anything from local produce and honey to candles and tea, from May 13 until October 21. Check out the Andersonville Farmers Market website for a full list of participating businesses and what else to expect when you shop.
Lucas Samaras: Sitting, Standing, Walking, Looking
Lucas Samaras developed an utterly unique approach to art making. While he experimented with a range of materials, his body and belongings were the primary subject of his photographs, sculptures, and drawings. Witness Samaras’s creative, engaged, and focused life, built through transforming everyday objects and actions through ceaseless artistic exploration. See this exhibit now through July 20, 2026.
Jewels of Spring: Lincoln Park Conservatory Flower Show
The 2026 spring flower show at the Lincoln Park Conservatory, “Jewels of Spring,” highlights the amazing flowers of the Tower of Jewels, also known as Echium or Pride of Madeira. It’s a dramatic, colorful plant which grows flower spikes that are two to three feet tall. Accompanying these gems are a host of our favorite spring beauties, tulips such as ‘Gold Rush’ and ‘Flaming Flag’, ‘4D Violet Ice’ African daisies, Cymbidium Orchids, Delphinium ‘Cobalt Dreams’, and Primula ‘Wild Flame Shades’. All are planted against a backdrop of our treasured camelias, azaleas, peonies, and hydrangeas. See this magnificent flower show until May 10.
The Movement You Need
Brendan Hunt — best known as Coach Beard on Ted Lasso — brings his one-man show to Steppenwolf Theatre Company. The Movement You Need draws on Hunt’s Chicago childhood, his lifelong connection to The Beatles, and the moment he finally met Paul McCartney. It’s funny, nostalgic, and a must-see mashup for Chicago Beatles and Ted Lasso fans. The show closes May 10, so grab your tickets while you can at The Movement You Need.
Carroll Dunham: Drawings, 1974-2024
Visit the Art Institute of Chicago — a 2026 Make It Better Foundation Philanthropy Award Winner — now through June 1, 2026 for a chance to see a unique exhibit featuring the work of Carroll Dunham. Over the course of five decades, Dunham has engaged in wide-ranging formal and thematic experimentation across various media, yet his drawings represent a distinct, interconnected body of work. Grab your tickets and find information on the Art Institute website.
FAULT at Chicago Shakespeare
Television star Enrico Colantoni and Golden Globe winner Teri Hatcher star in a wickedly dark new comedy directed by Jason Alexander. Full of blistering humor and searing revelations, Fault makes the case that being honest with ourselves might be the trickiest game we play in life and love. Catch it through May 24 at Chicago Shakespeare Theatre.
Second Saturdays at the Goodman
Saturdays at the Goodman are family-focused, intergenerational workshops centered on joy, creativity, and sharing space, held now through July 2026. Join them to participate in workshops facilitated by Goodman Teaching Artists as they celebrate creativity and the art of storytelling. Second Saturdays are ideal for littles (ages 4-10), and their families. Find more details online at Goodman Theatre — a 2026 Make It Better Foundation Philanthropy Award Winner.
Ruthless! The Musical at Citadel Theatre
Eight-year-old Tina is a charming, sociopathic child star who’ll stop at nothing to land the lead role in her school musical. As her ambitious mother, Judy, transforms from a naive housewife to a Broadway diva, Tina’s psychotic drive for fame escalates, leading to a hilariously dark and twisted musical journey. The show runs through May 17 at Citadel Theatre.
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May 1-3: Mexico Fest
Join other Chicagoans for the free Global Connections celebration of Mexico Fest at Navy Pier! Experience an authentic cultural celebration featuring amazing live music, dance, performances, art, crafts for all ages, and more. To find tickets and the full weekend line-up of events, visit Mexico Fest.
May 1-3: Trading Card Con Chicago
What started as a modest meetup for Pokémon fans has evolved into one of the country’s largest trading card convention series. It was built on the idea that the TCG community needed more than a marketplace — it needed something immersive. Now, Trading Card Con draws thousands of attendees to cities across the country each year, offering a welcoming space for collectors to trade and connect with other fans.
May 1-3: The Merry Wives of Windsor at Chicago Shakespeare
The secret lives of Windsor wives reveal more than just dirty laundry in an endlessly entertaining new take on Shakespeare’s most raucous comedy. Acclaimed director Phillip Breen brings together an ensemble cast stacked with some of Chicago’s most talented actors to create an endlessly entertaining new take on the play. Grab your tickets while you can, running only until May 3.
May 3: Lakefront Loop 5k
The annual Lakefront Loop 5K will kick off at 8am, followed by the Kids Dash at 9am. The 5K is completely within the Pier grounds, and the route will incorporate the Northwestern Medicine Wellness Way fitness trail, as well as the iconic North and South Docks. Register at Lakefront Loop 5k.
May 3: Fun Fest | 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! Guests will enjoy performances by Jazz Combos, Jazz Bands, Orchestras, Choral Ensembles, and Chamber Music Groups. Register online to join in on the music, food, drinks, raffle, and more. Details at Midwest Young Artists Conservatory.
May 8-10: Mother’s Day at Navy Pier
Celebrate the moms in your life with a Mother’s Day brunch at Offshore or Reunion, a scenic cruise on Lake Michigan, a ride on the iconic Centennial Wheel, or a breathtaking experience at Flyover. Treat her to some shopping at the unique boutiques and stores throughout Navy Pier or enjoy dinner at Lirica. Make it a full experience and book a room at the Sable Hotel or cap it off with tickets to Chicago Shakespeare Theater’s latest production.
May 9: Music Matters hosted by the Ravinia Associates Board
Join Ravinia for an exciting gala benefit, supporting Ravinia and the Reach Teach Play education and community programs. Guests will enjoy a cocktail hour, silent and live auction, engaging musical performance featuring the Ravinia Jazz Scholars, dinner, drinks, and dancing in the new “Audrey Afterparty.”
May 14: Evanston Arts & Craft Beverage Crawl
What sets this crawl apart is its focus on locally owned businesses and what they’re pouring and plating — from Evanston-made boozy beverages to thoughtful food pairings served throughout the three-hour event. Along the way, you’ll pass stops featuring local artists’ work and the occasional live performance, with a goodie bag at the end. With dozens of vendors in the mix, it’s a great way to spend an afternoon. Find details and tickets at Evanston Arts & Craft Beverage Crawl.
May 15-17: Lincoln Park Mayfest
Start festival season in the city at the annual Lincoln Park Mayfest. The lineup includes live music from local acts, plus the Spring Fine Art Mart, where artists from Chicago and beyond showcase their work. Add in food vendors and a mix of activities, and it’s an easy way to spend a spring weekend. Head to Lincoln Park Mayfest for what to know before you go.
May 16-17: Midwest Bonsai Society Spring Show & Sale
The Midwest Bonsai Society Spring Show & Sale returns to the Chicago Botanic Garden this May for its 20th anniversary. 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 at Chicago Botanic Garden.
May 16-17: Skokie Festival of Cultures
A longtime local tradition, the Skokie Festival of Cultures returns to Oakton Park this summer, bringing together music and dance performances, interactive cultural booths, a dedicated kids’ activity area, the festival’s signature flag display, and a wide range of food and drink vendors. It’s an easy way to spend time moving between cultures, performances, and flavors in one place. Find more details at Skokie Festival of Cultures.
May 16-17: Lincoln Roscoe Art + Craft Fair
Returning to Lakeview Roscoe Village again this summer, 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.
May 20: Saint-Saëns, Vieuxtemps, and Fauré – Chamber Music Society of Lincoln Center
Paris has long been a hub for composers who infused their chamber music with rich textures and emotional depth, from Saint-Saëns’s elegantly crafted trio to Fauré’s dramatic piano quartet. This program celebrates these French masters, offering a journey through vibrant melodies and poignant harmonies. Run Time: 1 hour 40 minutes. The show will be held at Harris Theater, a 2026 Make It Better Foundation Philanthropy Award Winner.
May 23: Memorial Day Fireworks at Navy Pier
Navy Pier kicks off their summer fireworks series this month just before Memorial Day — held on May 25. 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.
May 22-24: Belmont-Sheffield Music Fest
Now in its fourth decade, the Belmont-Sheffield Music Fest returns to Lakeview with a lineup of local tribute bands, food and drinks, and artisan vendors. Find more at Belmont-Sheffield Music Fest.
May 23-24: Randolph Street Market Festival
Vendors from across the country gather at the Randolph Street Market Festival in the West Loop, filling it with art, antiques, vintage décor, ephemera, indie and vintage fashion, jewelry, vinyl, and global goods. The European-style flea market feel, with live music woven in alongside the shopping and a lineup of food vendors.
More from Better:
- David Byrne’s ‘Theater of the Mind’ Turns Neuroscience Into an Immersive Experience
- Patti Smith, Joined by Jeff Tweedy, Sings ‘People Have the Power’ and Urges Sold-Out Crowd to ‘Use Your Voice’
- More Adults Are Being Diagnosed With Autism — Here’s Why the Right Therapy Approach Matters
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 Chicago.
