May events in Chicago are just a sneak peek for all of the incredible things do in Chicago throughout the summer months.
With festivals, farmers markets, and celebrations for Mother’s Day and Memorial Day, Chicago in May is filled with fun activities that really show off why Chicago is such a great city.
Clear your calendar for the best May events in Chicago!
The Best Things to Do in Chicago This May
Use the navigation below to see what’s happening in Chicago in May 2025. Skip to big events, some classic must-dos, and my handpicked recommendations for what to do this month. Keep an eye out! Events might change, and I might throw in some fun surprises just for kicks!
Top Events: Must-attend events of the month.
Recurring Activities: Regular events worth adding to your calendar.
The Curated List: Personal recommendations for unique Chicago experiences.
Top May Events in Chicago
Discover the biggest and most popular May events in Chicago. From Chicago neighborhood festivals to affordable and free things to do.
Chicago Farmers Markets
May – October | Various Locations
May kicks off outdoor farmers markets in Chicago. Now through the fall you can find fresh fruit, vegetables, flowers, baked goods and more at various neighborhood farmers markets in the city of Chicago.
Chicago Humanities Festival
May 1 – June 13th | Various Locations
Chicago Humanities Festival continues throughout the month of May in Chicago. The culturally focused event brings together leading authors, activists, and artist who engage in discussions on art, politics, and culture and more.
Switch on Summer
May 10th | Grant Park
Now in it’s 11th consecutive year, Switch on Summer is a free Chicago event in May that celebrates the switching on of historic Buckingham Fountain and a symbolic start of the summer season. This event will also preview the
Park District’s popular Night Out in the Parks summer events which bring cultural events to all 77 neighborhoods in Chicago throughout the summer.
Chicago Cabaret Week
May 9th -18th | Various Locations
If you’re looking for entertainment in Chicago that brings together song, music, and theater together—check out Chicago Cabaret Week. Featuring 95 performers across 17 intimate venues throughout Chicagoland, this ten-day festival showcases Chicago’s top cabaret artists performing blues, Broadway, burlesque, jazz, R&B, American Songbook, French chanson, and world music.
Lincoln Park May Fest
May 16 – 18th | 1000 W. Armitage Ave., Chicago, IL 60614
Kick off summer in Chicago with Mayfest this month in Chicago, one of the first major outdoor festivals of the year. This Chicago street festival takes place in the heart of Lincoln Park. Expect performances from top local Chicagoland bands plus a variety of food and drink vendors. This event also features the new Spring Fine Art Mart featuring local and national fine artists.
Mother’s Day Brunch and Activities in Chicago
May 11 | Various Locations
How will you plan to celebrate your mother, grandmother, or mother figure in Chicago? Try brunch of fun activity that’s perfect for any woman in your life.
Here are a things to do and place to try:
- Book an experience at the Lip Lab for Mother’s Day in the West Loop
- Mother’s Day Brunch at sister restaurants Petite Vie (Western Springs) and Vistro Prime (Hinsdale)
- Dearly Beloved Brunch Special
- Complimentary Cocktail for Mom’s during Mother’s Day at e.t.c. Chicago
- Special tasting menu and limited time cookie plate during Mother’s Day at Brindille
- A Sweet celebration for Mom from Sweet Mandy B’s
- Grand opening of Wild Hare music venue and rooftop bar in the West Loop
Pullman Railroad Days
May 17th – 18th | Pullman Exhibit Hall
History buffs and architecture lovers, save this May event in Chicago to your summer bucket list. Pullman Railroad Days is weekend event perfect for groups of all ages. Visit Chicago’s first National Park Monument and surrounding South Side neighborhood during a weekend filled with unique tours and activities.
Maxwell Street Market
May – October | West Maxwell Street &, S Halsted St, Chicago, IL
On select Sundays, enjoy this free event in Chicago. Starting in May, the Maxwell Street Market will open and include an eclectic mix of foods and finds. This year’s edition will also feature live entertainment and programming from cultural partners, and will incorporate nearby businesses and restaurants including several “Maxwell Street originals” with longstanding ties to the neighborhood.
Memorial Day Weekend in Chicago
May 23rd – May 26th | Various Locations
Find fun things to do during Memorial Day weekend in Chicago. From music festivals that take over Grant Park to Chicago street festivals, this weekend is the official start to the wonderful summer ahead. Here are five major events happening. Fore even more things to do, tap the button below.
- Sueños Music Festival : The ultimate music festival bringing Reggaeton and Latin Artists from all across the globe to Chicago.
- Mole De Mayo: A three-day outdoor food festival in Pilsen highlighting community, culture, lucha libre, and lots of mole.
- Randolph Street Market Festival: The indoor and outdoor flea market festival returns to the West Loop for a two day showcase of decor, rare finds, jewelry, fashion and more.
- Belmont-Sheffield Music Fest: Kick off your holiday weekend with a music festival in the heart of Lakeview. The 40th year of this festival will include live music from tribute bands and local artists, mouthwatering food, and plenty of vendors.
- Chicago Memorial Day Parade: This one day event is a parade that honors all men and woman who made the ultimate sacrifice in defense of our country with a wreath laying ceremony beginning at 11 a.m. before the parade processional.
Summer Saturday Fireworks at Navy Pier
May 24th – August 30th | Navy Pier
If you’re looking for free things to do in May in Chicago, nothing beats watching the summer fireworks at Navy Pier. This outdoor event is perfect for groups of all ages to enjoy.
Looking for Chicago events and things to do in Chicago this weekend? Check out the events calendar.
Recurring Fun Things to Do and Experience in May
Looking for fun activities and things to do in Chicago in May? Explore this list of ongoing events and experiences happening all month long.
- Architecture Boat Tour: Experience Chicago’s stunning skyline on a Chicago boat tour, perfect outdoor activity for warm weather.
- Chicago Crime & Mob Bus Tour: Step into the city’s darker history and discover infamous crime spots.
- The Escape Game Chicago: Solve puzzles in immersive escape rooms in downtown Chicago.
- Skydeck Chicago & Navy Pier Ferris Wheel: Marvel at the city’s skyline from these landmarks at wallet-friendly prices.
- See your favorite sports team line: Grab great seats for a Chicago Cubs or White Sox game.
- Interactive Museums: Capture Insta-worthy photos in interactive museums like the Museum of Ice Cream or the colorful Color Factory.
- Museum Free Days: Take advantage of free or discounted admission at museums.
The Curated List of Chicago Events in May
Here’s The Haute Seeker’s curated list of the best events, activities, and coolest events to check out during the month of May.
12th Annual Greater Englewood Unity Day
What: The largest community clean-up in Chicago with over 2,500 volunteers, followed by a celebration featuring local families, youth, and community leaders. Hosted by Imagine Englewood If.
When: May 3, 2025
Link for more information: imagineenglewoodif.org/unityday
Marché Privé: A Curated Luxury Pop-Up Market
What: A free, daytime Derby Day social and vendor event in Hyde Park Chicago celebrating BIPOC entrepreneurs with music by DJ Tess, Derby Day fashion, and a luxury shopping experience.
When: May 3, 2025
Link for more information: Marché Privé Market
Pilsen’s Cinco de Mayo Bar Crawl Party
What: The biggest Cinco De Mayo Chicago celebration and bar crawl in Chicago, with free entry to 8 bars, DJs at every venue, and a free cocktail at each stop. When: May 3, 2025
Link for more information: Pilsen’s Cinco de Mayo Bar Crawl Party
The October Nights: Calling All Lovers Tour
What: See R&B powerhouses Tamar Braxton, October London, and Ro James live in one of the most soulful Chicago concerts May 2025.
When: Sunday, May 4, 2025
Purchase Tickets: The Octobers Nights Tour
Chicago Does the Met Gala
What: Attend the 4th annual “Chicago Does the Met,” a red carpet-style event celebrating Black fashion and cultural excellence–a red carpet celebration of Black fashion and cultural excellence.
When: May 5, 2025
Link for more information: Chicago Does the Met Gala
Mother’s Day Gospel Celebration at House of Hope
What: An epic Gospel musical concert featuring Fred Hammond, Marvin Winans, Marvin Sapp, Donald Lawrence, and Jekalyn Carr.
When: May 9, 2025
Link for more information: Mother’s Day Gospel Celebration
Saturday Night at the Zoo – An Adults-Only Evening at Lincoln Park Zoo
What: A 21+ after-hours Chicago nightlife event featuring live music, a DJ, karaoke, lawn games, drinks, and animal exhibits. When: May 10, 2025
Link for more information: Adults Night at Lincoln Park Zoo
Mel Robbins – Let Them Tour
What: Author and motivational speaker Mel Robbins brings her powerful Let Them Theory live to Chicago, inspiring audiences to release expectations and embrace authenticity
When: May 11, 2025
Link for more information: Mel Robbins on Tour in Chicago
Wine Country: Cowboy Carter Meets Wine Country
What: Sip curated wines and cocktails, snack on tacos, and dance to Beyoncé-inspired DJ sets in this themed wine night by Samples & Samples.
When: May 16, 2025
Link for more information: Wine Country Sampling Event
Renegade Craft Fair – Spring Edition
What: Shop over 250 independent makers at this vibrant spring craft fair in the heart of Andersonville during this top May festival in Chicago.
When: May 17 – 18, 2025
Link for more information: Renegade Craft Fair Spring Market
Wine Fest on North Avenue Beach
What: Relax beachside at North Ave. while sipping a variety of wines, enjoying the lakefront breeze, and soaking in a sunset social vibe.
When: May 30, 2025
Link for more information: Wine Fest Chicago Beach
The Queens! 4 Legends. 1 Stage.
What: Chaka Khan, Patti LaBelle, Gladys Knight, and Stephanie Mills come together for one night only to celebrate their legendary careers at the United Center
When: May 30, 2025
Link for more information: The Queens Tour Tickets
Things to Know About May in Chicago
What’s the weather like in Chicago during May?
May is when Chicago finally starts to feel like spring—and sometimes even summer. Chicago weather in May will have more sunny days, longer evenings, and trees and flowers in full bloom. Temperatures usually range from the low 60s to mid-70s°F (around 16–24°C), but don’t be surprised by the occasional chill or rainy day. Layers are still a smart choice, especially for lakefront outings or late nights.
Is May a good time to visit Chicago?
Is May a good time to visit Chicago?
Absolutely. May is one of the most exciting months to explore the city, especially if you want to avoid peak summer crowds. Visit Chicago in May for street festivals, outdoor patios, farmers markets, music festivals and so much more!
What should I wear in Chicago in May?
What should I wear in Chicago in May?
Think spring-to-summer transitional outfits. Lightweight jackets or cardigans are great for cooler mornings, but you’ll likely want breathable layers for the afternoon. Sneakers or comfy walking shoes are a must if you plan to explore on foot, and always have a small umbrella on hand—Chicago weather can surprise you.
What to Look Forward to in May
May in Chicago is just a taste of all the awesome things happening during the summer. Pace yourself, soak it all in, and consider this just the warm-up for an unforgettable summer in the city of Chicago.
