31 of the Best Things to Do in Chicago This May

From concerts and shows to new museum exhibits and festivals, here are the can’t-miss events around Chicago this May.


May 9-12: Margaret Trudeau: Certain Woman of An Age

Margaret Trudeau at The Second City
Margaret Trudeau (Photo by Kirsten Miccoli.)

Margaret Trudeau, author, actress, and mother of Canadian Prime Minister Justin Trudeau, will bring her staged performance (directed by Kimberly Senior) to Chicago for a limited engagement. UP Comedy Club, 230 W. North Ave., Chicago


May 5: Derek Hough

This solo tour from Derek Hough of “Dancing With the Stars” will include a variety of dance styles, from ballroom to hip-hop. Rosemont Theatre, 5400 N. River Road, Rosemont

May 11: Balanchine and Beyond Spring Series: ENCORE!

Ballet Chicago Studio Company will perform “Hansel and Gretel” (Duell/Humperdinck), “Concerto Barocco” (Balanchine/Bach), and more. Harris Theater, 205 E. Randolph Drive, Chicago


May 3-4: Night Lights

This brand new Chicago Botanic Garden display will feature 3,000 luminaries in various designs, plus light bites and drinks available for purchase. Chicago Botanic Garden, 1000 Lake Cook Road, Glencoe

May 4: Chicago Beer Classic

Sample beer from more than 30 Chicago breweries and take part in games and activities on Soldier Field. Soldier Field, 1410 Museum Campus Drive, Chicago

May 5: One Book Everybody Reads

Author Rosellen Brown will discuss her book “The Lake on Fire,” Wilmette Public Library’s 2019 One Book Everybody Reads selection. Wilmette Junior High School, 620 Locust Road, Wilmette

May 5: Touch A Truck Family Festival

Kohl Children's Museum: Touch a Truck
Photo courtesy of Kohl Children’s Museum.

Kohl Children’s Museum will present this annual event with more than 30 full-sized vehicles, food trucks, music, face painting, and more to benefit the museum. Northeastern Illinois Public Safety Training Academy, 2300 Patriot Blvd., Glenview

May 10: Manifest 2019

This annual festival features more than 100 free public programs from Columbia College Chicago students in art, music, and visuals. South Loop, Chicago

May 11-19: Evanston Literary Festival

This annual festival “celebrates the literary culture of Evanston” with author readings, workshops, a book fair, and more. Various

May 17: Chicago Dogs Home Opener

Chicago Dogs home opener
Squeeze, Chicago Dogs mascot (Photo by Daniel Boczarski.)

The Chicago Dogs (who recently signed former Cubs pitcher Carlos Zambrano) are ready to start a new season with promotions like post-game fireworks on Saturdays and Wiener Wednesdays (with special uniforms and hot dog specials) all summer long. Impact Field, 9850 Balmoral Ave., Rosemont

May 17-18: Palm Tree Pajama Party

Sleep at Navy Pier in the Crystal Gardens during this new event, which will also feature rides, crafts, music, dancing, movies, yoga, and breakfast. Navy Pier, 600 E. Grand Ave., Chicago

May 17-19: Lincoln Park Wine Fest

Sample more than 80 wines as you enjoy food and music and meet artisans. Jonquil Park, 1001 W. Wrightwood, Chicago

May 18: World’s Largest HIIT Workout

Join Orangetheory® Fitness in a Guinness Book of World Records attempt for World’s Largest HIIT Workout while also raising money for Augie’s Quest to Cure ALS. Wrigley Field, 1060 W. Addison St., Chicago

May 18-19: Skokie Festival of Cultures

Enjoy ethnic folk music and dance performances, dine on food and drinks from around the world, shop the merchandise bazaar, and more. Oakton Park, 4701 Oakton St., Skokie

Opens May 18: Cirque du Soleil’s VOLTA

Cirque du Soleil: VOLTA
Photo by Matt Beard. Costumes: Zaldy / ©2017 Cirque du Soleil Inc.

Cirque du Soleil will extend its Chicago engagement of this show by raising its Big Top outside Soldier Field. VOLTA features brand new acrobatics inspired by street sports. Soldier Field South Lot, 1410 Museum Campus Drive, Chicago

May 19: Andersonville Wine Walk

Sip and shop around Andersonville, where 28 businesses will participate in this 13th annual event. Check in at the new Swedish American Museum storefront, 5217 N. Clark, Chicago

Opens May 24: Nature Connects®: Art with LEGO® Bricks by Sean Kenney

View 15 large displays, including an eight-foot dragonfly, made entirely of LEGOs. The Morton Arboretum, 4100 Illinois Route 53, Lisle


Opens May 26: “Manet and Modern Beauty

For the first time in 50 years an Art Institute exhibit will focus solely on Édouard Manet, and this will be the first exhibit to focus on Manet’s work in the 1870s. Art Institute of Chicago, 111 S. Michigan Ave., Chicago

May 30: Shedd After Hours: Penguin Party

This 21+ event will feature cocktails, food, and penguin appearances with the Shedd team members that rehabilitate and release endangered African penguins. Shedd Aquarium, 1200 S. Lake Shore Drive, Chicago


May 6-7: Nancy and Beth

Actresses and musicians Megan Mullally and Stephanie Hunt make up this hilarious duo. City Winery Chicago, 1200 W. Randolph St., Chicago

May 19: Notorious RBG in Song

Supreme Court Justice Ruth Bader Ginsburg’s life is celebrated through song during this concert featuring her daughter-in-law and soprano/composer Patrice Michaels, pianist Kuang-Hao Huang, soprano Michelle Areyzaga, tenor Matthew Dean, and baritone Evan Bravos. Spertus Institute for Jewish Learning and Leadership, 610 S. Michigan Ave., Chicago


Opens May 3: “West Side Story

"West Side Story" at Lyric Opera of Chicago
Mikaela Bennett and Corey Cott in “West Side Story” at Lyric Opera of Chicago (Photo by Todd Rosenberg.)

Tony Award-nominee Corey Cott and Mikaela Bennett will star in this production of “West Side Story.” Lyric Opera of Chicago, 20 N. Wacker Drive, Chicago

May 10-19: “Rent

The 20th anniversary tour of “Rent” comes to Chicago for one week only. James M. Nederlander Theatre, 24 W. Randolph St., Chicago

Through May 12: “American Girl Live

This new musical “celebrates the power of girls and the strength of friendship.” Broadway Playhouse at Water Tower Place, 175 E. Chestnut, Chicago

Media Sponsorships

Make It Better is a proud media sponsor of these events:

May 7: The Woman’s Board of Rush University Medical Center’s 25th Annual Spring Luncheon

Hear from Mary Robinson, former president of Ireland and leader of the Mary Robinson Foundation—Climate Justice. Hilton Chicago, 720 S. Michigan Ave., Chicago

May 10: ELPC Gala

The Environmental Law & Policy Center welcomes author and MSNBC host Chris Hayes and U.S. Senator Tammy Duckworth for this gala and celebration. Radisson Blu Chicago, 221 N. Columbus Drive, Chicago

Additional events Make It Better is proud to support: