30 of the Best Things to Do in Chicago This September

30 of the Best Things to Do in Chicago This September (Leon Bridges)

Fall’s arrival in Chicago and the surrounding suburbs brings a plethora of can’t-miss events, from theater and comedy to music and museum exhibits.


Sept. 11 to Oct. 14: “Tootsie

The 1980s hit movie gets a stage-ready makeover with this musical, which follows actor Michael Dorsey and his drag pursuits in alter-ego “Dorothy Michaels.” Cadillac Palace Theatre, 151 W. Randolph St., Chicago, 312-384-1502

Opens Sept. 20: “Downstate

This moving show follows four sex offenders sharing a group home in downstate Illinois as they negotiate their place in a neighborhood that doesn’t want them and in a society that doesn’t want to forgive them. Steppenwolf Theatre Company, 1650 N. Halsted St., Chicago, 312-335-1650


Opens Sept. 4: “Made in America (Some Assembly Required)

The Second City’s laughs are 100 percent made in the USA in their latest take on our nation, a comedic revue featuring different material every month this fall. UP Comedy Club, 230 W. North Ave., Chicago, 312-662-4562

Sept. 14: Russell Peters

The Canadian stand-up comedian and actor hits the Chicago Theatre stage with all new material, including plenty of entertaining interactions with the audience. The Chicago Theatre, 175 N. State St., Chicago, 312-462-6300

Thursdays: “Dreamboat

This show highlights solo performances from LGBTQIA+ identifying performers and culminates in an improv set by the all-LGBTQIA+ team Dreamboat. iO, 1501 N. Kingsbury St., Chicago, 312-929-2401


Through Sept. 2: Chicago Jazz Festival

Since 1979, this festival’s mission has been to showcase Chicago’s vast jazz talent alongside national and international artists to encourage and educate an audience of all ages. Millennium Park, 201 E. Randolph St., Chicago, 312-744-3316

Sept. 7: Stars of Lyric Opera at Millennium Park

Pack a picnic basket and bring your friends to enjoy a performance featuring acclaimed artists Michael Fabiano, Maria Agresta, and Danielle de Niese, in performance with the Lyric Opera Orchestra and Chorus. Jay Pritzker Pavilion, Millennium Park, 201 E. Randolph St., Chicago, 312-827-5600

Sept. 7-23: World Music Festival

This citywide, 11-day festival has attracted more than 650,000 concertgoers and has presented more than 650 artists from over 80 countries since it began in 1999. Various locations, 312-744-8523

Sept. 14: Gipsy Kings featuring Nicolas Reyes and Tonino Baliardo

Chicago Events in September 2018: Gipsy Kings
Gipsy Kings (Photo courtesy of Ravinia Festival.)

Spend an evening with this internationally beloved band, which has become best known for its iconic marriage of traditional flamenco styles with Western pop and Latin rhythms. Ravinia Festival, 200 Ravinia Park Road, Highland Park, 847-266-5100

Sept. 30: 4u: A Symphonic Celebration of Prince

Experience Prince’s extensive musical catalog at this musical celebration, which will be performed with a full symphony orchestra. The Chicago Theatre, 175 N. State St., Chicago, 312-462-6300

Sept. 30: Madeleine Peyroux

Sway to the rhythms of this American singer-songwriter, whose repertoire spans jazz standards in English and French, American country classics, and blues. Thalia Hall, 1807 S. Allport St., Chicago, 312-526-3851


Sept. 15: Prime Time: #FutureSelf

Experience the MCA museum as a lively and immersive backdrop for works by Chicago artists and key cultural groups in the city with this after-hours series, which features live music, performance art, and interactive programs. Museum of Contemporary Art Chicago, 220 E. Chicago Ave., Chicago, 312-397-4010

Sept. 21: Singers & Songwriters: Dessa

Rapper, singer, and essayist Dessa talks poetry, lyrics, and her new book, “My Own Devices.” American Writers Museum, 180 N. Michigan Ave., Chicago, 312-374-8790

Opens Sept. 26: Hairy Who? 1966-1969

Presented on the 50th anniversary of their final Chicago show, Hairy Who? is the first major comprehensive retrospective dedicated solely to the original exhibition of the same name. The Art Institute of Chicago, 111 S. Michigan Ave., Chicago, 312-443-3600

Closes Jan. 6, 2019: Antarctic Dinosaurs

Chicago Events in September 2018: Field Museum
Photo courtesy of the Field Museum.

This exhibit features life-size models of dinosaurs so new to science, they haven’t yet been assigned species names. Their real fossils are also on display. Field Museum, 1400 S. Lake Shore Drive, 312-922-9410


Aug. 31 to Sept. 3: African Festival of the Arts

Attendees of this festival are transported to cultures across the diaspora with interactive engagements, drumming, collectible artifacts, and a variety of program spaces. Washington Park, 5531 S. King Drive, Chicago, 773-955- 2787

Sept. 1-30: Cindy’s x Doors Open Dishes

Dine for a cause with the debut of Doors Open Dishes, a fundraising initiative supporting essential programs for individuals with developmental disabilities by creating client-inspired dishes at restaurants around town. Join them for their first partnership at Cindy’s, where proceeds from chef Christian Ragano’s dish will benefit Lincoln Square’s Gateway to Learning. Cindy’s at the Chicago Athletic Association, 12 S. Michigan Ave., Chicago, 312-792-3502

Sept. 8: Adler Planetarium Celestial Ball

Chicago Events in September 2018: Adler's Celestial Ball
The Celestial Ball raises money for Adler education programs. (Photo courtesy of Adler Planetarium.)

Hosted by the Adler Women’s Board, this annual black-tie gala raises funds for a variety of the venue’s year-round programming. Adler Planetarium, 1300 S. Lake Shore Drive, Chicago, 312-553-2000

Sept. 8-9: Lakeview East Festival of the Arts

This fest showcases more than 150 juried artists featuring paintings, sculpture, photography, furniture, and jewelry, all alongside live demos, entertainment stages, and family activities. Broadway Street between Belmont and Hawthorne, Chicago, 773-348-8608

Sept. 10: Chef Takeover for Charity Dinner Series at MFK

Chef Alisha Elenz welcomes guest chef Diana DaVila of Mi Tocaya for a five-course dinner with drink pairings. All proceeds go to United We Dream, the largest immigrant youth-led community in the country. MFK, 432 W. Diversey Parkway, Chicago, 773-857-2540

Sept. 14: Friday Night Flights at Chicago Riverwalk

This scenic promenade and urban recreation waterfront park will host more than 15 award-winning breweries from across the city — all against the backdrop of Chicago’s iconic skyline. Chicago Riverwalk between Clark Street and Franklin Street, Chicago, 312-567-8500

Sept. 14-16: Fulton Market Harvest Festival

Curated by Chef Stephanie Izard, this neighborhood fest unites the city’s top culinary talent with notable chefs from around the country for three days of popup dinners, classes, and demos. Fulton Market and Halsted Street, Chicago

Sept. 15: Dance-Scape

The final outdoor Ragdale Ring performance is an interactive movement piece inspired by the beauty of Ragdale’s prairie landscape and the dynamic Ring design. This family-friendly program includes long-legged stilt dance, live music, and students from the Hubbard Street Pre-Professional program. Ragdale, 1230 N. Green Bay Road, Lake Forest, 847-234-1063

Sept. 15-16: Ravenswood ArtWalk

The Ravenswood ArtWalk moves into its 14th year ready to again welcome hundreds of artists and thousands of visitors from across the Midwest. North Ravenswood Avenue between Lawrence Avenue and Irving Park Road, Chicago, 773-728-3890

Sept. 22: YAS! Fest

Chicago Events in September 2018: Ravyn Lenae
Ravyn Lenae, a graduate of Chicago High School for the Arts, will open for the fest’s headliner, Desiigner. (Photo by Sam Kfare.)

The new YAS! Fest will showcase teen artists in dance, theater, music, spoken word, the visual arts, and more. Millennium Park, 201 E. Randolph St., Chicago, 312-744-3316

Sept. 26: National Geographic Live — “When Women Ruled the World”

Dr. Kara Cooney, professor of Egyptian art and architecture at UCLA, takes “a look at a time in ancient history when women ruled the world.” Auditorium Theatre, 50 E. Congress Parkway, 312-341-2300

Sept. 26-30: Chicago Gourmet

Each September, celebrity chefs headline cooking demos on two stages, popular wine and mixology seminars serve up the coolest trends in a glass, and a serious lineup of food, wine, spirits, and beer tastings keeps the crowd hungry for more. Millennium Park, 201 E. Randolph St., Chicago, 312-380-4129

Sept. 27-30: EXPO Chicago

EXPO CHICAGO, The International Exposition of Contemporary and Modern Art
Photo courtesy of EXPO Chicago.

Opening the fall art season each September, EXPO Chicago hosts leading international art galleries presented alongside one of the highest-quality platforms for global contemporary art and culture. Navy Pier, 600 E. Grand Ave., Chicago, 312-513-4002

Sept. 27-30: Disney on Ice: Frozen

Anna and Elsa will take to the ice along with Kristoff, Sven, and everyone’s favorite snowman Olaf as Disney on Ice this time brings the full story of Frozen to Chicago. And don’t worry, there will still be plenty of special appearances by your other favorite Disney pals, including Mickey, Minnie, Buzz and Woody! Allstate Arena, Rosemont

Sept. 30: Blocktoberfest

Dusek’s Board & Beer is bringing its free, family-friendly community block party back to Pilsen, featuring craft beer and cocktails, German-inspired food, and a special fun zone for kids. 1227 W. 18th St., Chicago

Sept. 24: Leon Bridges

Chicago Events in September 2018: Leon Bridges
Leon Bridges (Photo by Jack McKain.)

Hear the tracks that helped to quickly land this American gospel and soul singer-songwriter on the map, in addition to works from his newest album release, “Good Thing.” Aragon Ballroom, 1106 W. Lawrence Ave., Chicago


Media Sponsorships

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

Sept. 7: Children’s Home & Aid Woman’s Board 98th Annual September Gala

This year’s gala will raise funds for three incredible early childhood centers in the Chicago area. The Union League Club of Chicago, 65 Jackson Blvd., Chicago

Sept. 9: Butler International & Prince of Wales Cup

Don your best hat and enjoy a day of polo and people-watching (spoiler alert: this event is really fun) as the Wales Polo Team returns to Oak Brook for the final match in the International Polo Series. Oak Brook Polo Club, 2606 York Road, Oak Brook

Sept. 16: Rock the Boat Against Sex Trafficking

Support Selah Freedom’s work to end sex trafficking as you cruise around Lake Michigan on the Anita Dee II yacht. The afternoon will also include a live auction, entertainment, and more. The Boat Docks at DuSable Harbor on the Chicago River, 111 N. Lake Shore Drive, Chicago

Sept. 24: After School Matters Gala 2018

This annual gala will feature a cocktail reception, teen performances, dinner, and more, all to support After School Matters’ work providing after-school and summer programs to more than 15,000 teens every year. Wintrust Arena, 200 E. Cermak Road, Chicago

Sept. 26: Moving Forward Together

Support Philanthropy Award winner Mercy Housing Lakefront during this evening of networking, dinner, awards, and more. The Drake Hotel, 140 E. Walton Place, Chicago

Additional events Make It Better is proud to support:


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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