25 Things to Do in Chicago This May

Photo by Lance Anderson on Unsplash.

As we (finally!) say goodbye to winter, it’s time to get out and take advantage of everything Chicago has to offer. Here are 31 things to do in Chicago this month.


Closes May 20: “Jesus Christ Superstar

Things to Do in Chicago This May: "Jesus Christ Superstar"

2016-2017 London cast of “Jesus Christ Superstar” (Photo by Johan Persson.)

With music by Andrew Lloyd Webber and lyrics by Tim Rice, this global blockbuster tells the story of the final weeks in the life of Jesus Christ, from the perspective of Judas Iscariot. Lyric Opera of Chicago, 20 N. Wacker Drive, 312-332-2244

May 8-20: “The Wizard of Oz

Things to Do in Chicago This May: "The Wizard of Oz"

Photo courtesy of Carol Fox and Associates.

This production follows the iconic story of Dorothy as she makes the journey through Oz, refreshed for a modern audience as told through updated special effects and original songs composed by Harold Arlen. The Chicago Theatre, 175 N. State St., Chicago, 800-745-3000

May 18-20: Ballet Nacional de Cuba — “Don Quixote”

Things to Do in Chicago This May: Ballet Nacional de Cuba's "Don Quixote"

Ballet Nacional de Cuba’s Viengsay Valdés and Patricio Revé (Photo by Nancy Reyes.)

Ballet Nacional de Cuba returns to Chicago for the first time in 15 years with company director Alicia Alonso’s “Don Quixote,” putting a distinctly Cuban spin on the classic ballet. Auditorium Theatre, 50 E. Congress Parkway, 312-341-2300

May 29 to June 3: “Dirty Dancing

In this live performance, expect the same music, romance, and dancing that catapulted this film into worldwide fanfare. Cadillac Palace Theatre, 151 W. Randolph St., 312-977-1700


May 19: “Stories I Only Tell My Friends: LIVE!

Things to Do in Chicago This May: "Stories I Only Tell My Friends: LIVE!" with Rob Lowe

Rob Lowe (Photo courtesy of Margie Korshak, Inc.)

Following his sold-out debut, Rob Lowe is taking his one-man show, “Stories I Only Tell My Friends: LIVE!,” on a limited-run tour — inspired by the success of his two New York Times best-selling memoirs. Cadillac Palace Theatre, 151 W. Randolph St., 312-977-1700


May 4-10: Chicago Critics Film Festival

Created by the Chicago Film Critics Association in 2013, this festival offers a selection of films comprised of recent festival favorites and as-yet-undistributed works from a wide variety of filmmakers. Music Box Theatre, 3733 N. Southport Ave., Chicago, 773-383-9667


Closes May 4: Bach Week Festival

This 45th annual concert series will feature the world premiere of Marcos Balter’s new Bach-inspired work for solo cello, pianist Sergei Babayan in a Bach concerto and solo works, and the festival’s first performance of Bach’s Cantata 191. Various

May 26: 3rd Annual Chicago House Music Festival

DJs and live performances showcase the various sounds and styles of house music, the musical form born in Chicago that has gone on to revolutionize dance music internationally. Millennium Park, 201 E. Randolph St., Chicago 


May 12-26: Galleri Ramfjord Group Show

The iconic Norwegian gallery Galleri Ramfjord curates an exhibition of all Scandinavian artists. Vertical Gallery, 1016 N. Western, Chicago, 773-697-3846


Opens May 4: Flesh: Ivan Albright at the Art Institute of Chicago

More than 30 works from the museum’s collection present a focused retrospective of this “master of the macabre,” whose work even today retains the power to shock, move, and fascinate. The Art Institute of Chicago, 111 S. Michigan Ave., Chicago, 312-443-3600

May 4: Astro-Overnights at Adler Planetarium

Explore the Solar System at this after-hours, family-friendly event, which features new, hands-on programming, special sky shows, and the chance to spend the night under the stars or in an exhibit next to a planet. Adler Planetarium, 1300 S. Lake Shore Drive, Chicago, 312-922-7827 

Opens May 12: Never a Lovely So Real: Photography and Film in Chicago, 1950-1980

Things to Do in Chicago This May: "Never a Lovely So Real: Photography and Film in Chicago, 1950–1980" at the Art Institute of Chicago

Billy Abernathy. “Mother’s Day” from “Born Hip,” 1962. The Art Institute of Chicago. Gift of the Illinois Arts Council.

Providing a poetic survey of photographers and filmmakers who worked in neighborhoods across the city from the 1950s through the 1970s, this exhibition draws a comprehensive portrait of Chicago at the time. The Art Institute of Chicago, 111 S. Michigan Ave., Chicago, 312-443-3600


May 2: Selah Freedom Volunteer Connect Meeting

Selah Freedom is a national organization confronting sex trafficking. Meet the team and find out how you can get involved at this volunteer meeting. Willow Creek North Shore, 2200 Shermer Road, Glenview

May 5: 20th Annual Chicago Kids and Kites Festival

Kids of all ages will get swept up by this timeless spring tradition, when free kite kits are provided for children to build, decorate, and fly. Enjoy other family activities, too, such as professional kite flying demonstrations, balloon artists, and the Big Kite Candy Drop. Cricket Hill in Lincoln Park, Lake Shore and Montrose drives, Chicago

May 6: Touch-A-Truck Family Festival

Kohl Children’s Museum’s annual Touch-A-Truck festival returns for its 13th year with a special appearance by the Bigfoot Monster Truck, train rides, face painting, a balloon artist, food trucks, and more. NIPSTA, 2300 Patriot Blvd., Glenview

May 7: James Beard Awards

This evening celebrates the chefs and hospitality leaders who are making America’s food culture more exciting and diverse, including Chicago nominees Sarah Rinkavage (Marisol), Greg Wade (Publican Quality Bread), Abe Conlon (Fat Rice), and Lee Wolen (Boka, Somerset). Lyric Opera of Chicago, 20 N. Wacker Drive, Chicago 

May 15: Pinot in the City

Taste the wines that have put Oregon’s Willamette Valley on the map. Mingle with more than 70 winemakers from the region while you sip some of the region’s best Pinot Noir, Pinot Gris, Chardonnay and more. Morgan Manufacturing, 401 N. Morgan St., Chicago

May 18-25: Illinois Craft Beer Week

Things to Do in Chicago This May: Illinois Craft Beer Week

Explore more than 400 neighborhood venues via their craft beer selections, such as IPAs, sours, and imperials. Various 

May 19: TODO Chicago River Clean Sweep

Help maintain Chicago’s most treasured waterway on May 19, when TODO will be hosting its 6th annual Chicago River Clean Sweep — on kayaks. Kayak Chicago will supply the boats, bags, guides, and basic instruction for the clean-up, while a local band serenades paddlers. 1220 W. Le Moyne St., Chicago 

May 19: Star Wars Night at Guaranteed Rate Field

Cheer on the White Sox as they take on the Texas Rangers on Star Wars Night. The first 20,000 fans will receive a Hawk “Solo” Bobblehead. 333 W. 35th St., Chicago

May 19-20: Lincoln Park Wine Festival

This annual tasting event in Lincoln Park celebrates fermented grapes with more than 80 varietals, food, artists, a DJ, and food pairings. Jonquil Park, 1001 W. Wrightwood, Chicago, 773-868-3010

May 25: Chicago Dogs Opening Day

Things to Do in Chicago This May: Chicago Dogs

Impact Field (Photo by Daniel Boczarski.)

The Chicago Dogs, the Chicago area’s newest baseball team, will face the Kansas City T-Bones for their home opener at the state-of-the-art Impact Field in Rosemont. The team will play 50 games throughout the summer. Impact Field, 9850 Balmoral Ave., Rosemont, 847-260-2544

May 26: Chicago Memorial Day Parade

The City of Chicago’s Memorial Day Parade honors all men and women who made the ultimate sacrifice in defense of our country. State Street from Lake Street to Van Buren Street, Chicago

Opens May 26: Amazing Arachnids

Bookfield Zoo’s newest temporary exhibit is all about arachnids. In fact, the exhibit will feature 100 live arachnids (the largest public collection in North America). 3300 Golf Road, Brookfield, 708-688-8000

Opens May 26: Butterflies & Blooms

Spend a day at Chicago Botanic Garden, where you can see up to 500 butterflies at this exhibition. 1000 Lake Cook Road, Glencoe, 847-835-6801

May 26-27: Randolph Street Market

Since 2003, Chicago’s Randolph Street Market is a year-round shopping destination celebrating all things design and style, from home furnishings and art, to jewelry and global goods. 1341 W. Randolph St., Chicago

May 26-27: Belmont-Sheffield Music Fest

Kick off Chicago’s summer street fest season with this event, a gathering of top local tribute bands on the main stage, a second community entertainment stage, food, libations, and arts and crafts vendors. Sheffield Avenue from Belmont to Roscoe, Chicago, 773-868-3010

May 27: MB Bike the Drive

Things to Do in Chicago This May: Bike the Drive

Photo courtesy of the Active Transportation Alliance.

With Chicago recently being named the No. 1 bicycling city in America by Bicycling magazine, what better way to celebrate than with a ride on the city’s crown jewel roadway — Lake Shore Drive. Proceeds benefit Active Transportation AllianceJackson Street and Columbus Drive, Chicago, 312-967-1016

Media Sponsorships

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

May 6: Race for Humanity 5K and Kids 1K Fun Run

This annual race supports the mission of the Illinois Holocaust Museum “to empower individuals to speak out against hatred, prejudice, and indifference.” 9603 Woods Drive, Skokie

May 11: The People’s Music School Gala: Let It Shine

The People’s Music School serves roughly 700 students through programs supported by their annual gala. This year’s event will include a cocktail reception, seated dinner, and student and guest artist performances. Morgan Manufacturing, 401 N. Morgan St., Chicago

May 31: The Working Lunch

Celebrate 45 years of “speaking up, speaking out, and making change” at this Women Employed event. Laura S. Washington will moderate a conversation with Ai-jen Poo, Mónica Ramírez, and Andrea Pino. Hyatt Regency Chicago, 151 E. Upper Wacker Drive, Chicago


More from Make It Better: 

Nicole SchnitzlerNicole Schnitzler is a freelance writer who covers​ ​food, drink, ​travel, and ​lifestyle. When she is not planning her next adventure​​, she can be found​ ​commuting between bakeries, yoga classes,​ live music shows, and libraries ​in her hometown of ​​Chicago. She is most comfortable with a pen in one hand and a fork in the other. Nicole is also the founder of Doors Open Dishes, an initiative committed to keeping the doors open to the group homes and workshops of individuals with special needs by partnering with chefs and restaurants across the city. Follow her on Twitter (@Write_To_Eat) or on Instagram (@WriteToEat).




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