30 of the Best Things To Do in Chicago and the Suburbs in September 2023

Summer might be over but the fun and festivities around Chicago are always going strong. From food festivals and live music to performance art and community bonding — there’s always a new way to enjoy our great city. Check out our lineup of the best things to do in Chicago and the suburbs this September.

Don’t forget to tag us in your posts on Instagram @betterchicago

All Month

CLUE: A Walking Mystery

Was it the candlestick or the rope? In the Billiards Room or in the Library? Let’s find out! Now you too can be a part of the wicked mystery that surrounds CLUE — the beloved board game turned interactive fun in Chicago. By purchasing a ticket, you are becoming part of the hunt to find who the real killer is in a murder case gone cold. Are you up for the challenge? More details on just what to expect can be found on the CLUE: A Walking Mystery site, where tickets can also be bought — the event runs through October.

Block 37, 108 N. State St.

Art on the Mart

It’s come time for Art on the Mart to turn over its facade to the next artist installment — which beginning September 14 will belong to artists Yiyun Kang’s “Only in the Dark” and Charles Atlas’ “The Geometry of Thought.” Kang’s renowned work, which centers on the soon-approaching future, will be featured on the Mart for the first time ever, while Atlas’ project is a reprise once again gracing Chicago. For more details on these distinguished artists and to get a feel for the work that will be presented, visit Art on the Mart online.

222 W. Merchandise Mart Plaza


On show at the Red Orchid Theatre September 7 through the end of October is their latest production, Revolution, which “interrogates and celebrates the very nature of creating community and building friendships in our ever evolving, ever disconnecting world.” On her 26th birthday, Puff and her friends bring in her next chapter of her life with laughter, lightheartedness and maybe even a bit of danger. Sound intriguing? Catch the show while you can and visit the Red Orchid Theatre to secure your tickets.

1531 North Wells St.

Chicago Stories

This month, WTTW Chicago is ushering in a new kind of historic enlightenment with their series Chicago Stories, premiering September 22 with weekly episodes to follow. The eight-installment series takes a close examination of some of Chicago’s most iconic and impactful moments and figures — from the Great Chicago Fire to Ida B. Wells and much more. Tune in for the weekly episodes, sure to have all the nitty gritty details Chicagoan historians and locals alike can appreciate. Head over to WTTW for all the details on how to watch and what to expect.

Picasso: Fifty Years Later

Bacchanal with Kid Goat and Onlooker, by Pablo Picasso (1959)

In honor of the 50 year anniversary of Pablo Picasso’s death, around the world there are exhibits being held to showcase his work and his lasting impact on the world of art. One such exhibit will be held at the Elmhurst Art Museum — running September 9 through January. This three-part exhibition will include an introduction with works by Picasso and his contemporaries; as well as “a gallery dedicated to the demanding process of Picasso’s printmaking” and a presentation on “contemporary figurative artists today.” True art lovers will flock to an opportunity such as this, but it also welcomes anyone curious about the life and efforts of the late, great artist. Timed reservations can be made ahead of time by visiting the Elmhurst Art Museum.

150 Cottage Hill Ave., Elmhurst

Jack’s Pumpkin Patch Pop-Up

For many Chicagoans, fall means sweet treats, ciders, autumn-colored photo-ops and picking the perfect pumpkin. And luckily for us, Jack’s Pumpkin Patch Pop-Up is the annual opportunity to do all of that and more. On Goose Island, the seasonal festivities kick-off September 21 when Jack’s opens its doors to millennials looking for fun, parents seeking a family night out and anyone else who loves this season. Whether you plan on winding through the corn maze, having an inspired cocktail or just enjoying the fall air, you’ll want to head over to Jack’s Pumpkin Patch Pop-Up to grab your tickets first.

1265 West Le Moyne

American Psycho: The Musical

Wicker Park’s Chopin Theatre returns this season with yet another show ready to shock audiences. Join them from September 14 through the end of November for American Psycho: The Musical. Put on by Kokandy Productions, this “sexy and psychopathic new musical, based on the best-selling novel by Bret Easton Ellis” will delight audiences with its cruel intrigue and hit-like songs. Check out all the details, and secure your tickets, by visiting the Chopin Theatre online.

1543 West Division

September 1: Hollywood Nights: The Bob Seger Experience

Whether you love the deep tracks or just the hits, Hollywood Nights: The Bob Seger Experience is coming to Aurora to rock Chicagoland for one night only. Enjoy the music of one of America’s favorite rock legends while spending the last days of summer outside with the community. The show starts at 8pm at RiverEdge Park; reserve your tickets now by visiting the Hollywood Nights: The Bob Seger Experience.

360 N. Broadway, Aurora

September 1-3: Chicago Jazz Festival

All throughout Chicago, the city is overflowing with talented musicians. Countless outdoor festivals cater to a plethora of genres, but few do justice to jazz music like the Chicago Jazz Festival held at Millennium Park and the Chicago Cultural Center every summer. This four-day fest actually kicked off last month, but real fans know the event is still playing into the first week of September. If you fancy jazz music, there is no better place to be than the Chicago Jazz Festival — visit their website for entry details.

September 1-3: ARC Music Festival

House music was born in Chicago, so it’s no wonder the ARC Music Festival — held at Union Park and dedicated strictly to that genre — is returning for its third year just as strong as before. Dance to your heart’s content to some of your favorite local and international DJs all while you take in the final days of this Chicago summer. Tickets and programming information can be found on the ARC Music Festival website.

1501 W. Randolph St.

September 3: Bike the Drive

Among many things, Chicago is a city that supports an influx of bicyclists, especially in the summer months. In honor of that, Fifth Third Bank is sponsoring the annual Bike the Drive event — where riders can cruise along DuSable Lake Shore Drive, an extraordinarily rare opportunity. Riders are encouraged to bike as much or as little as they please along the 30-mile course, all in support of raising funds for Active Transportation Alliance. Reservations are cheaper when you purchase ahead of time, so ride over to Bike the Drive online for more information and to save your spot.

September 3: Illinois Mycological Association Display & Sale

Don’t let the name fool you, the Illinois Mycological Association Display & Sale at the Chicago Botanic Garden is nothing more than a wholesome way to peruse, purchase and learn about the many varieties of mushrooms that exist. If you fancy some fungi, you’ll want to stop by Burnstein Hall to view the “50 to 100 varieties of mushrooms foraged from area forests in the days prior to the show.” Sound up your alley? Visit the Chicago Botanic Garden for entry details.

1000 Lake Cook Rd., Glencoe

September 8-10: Taste of Chicago

While neighborhoods across the city have had their own pop-up Tastes throughout the summer, none compare to the mother of all foodie festivals, Taste of Chicago — held annually in Grant Park. Since 1980, Chicagoans have been flocking to this fest to sample an array of the best dishes in the city from countless vendors. Summer isn’t over yet, so hit the park to grab a bite and bring a friend or the family while you’re at it. Taste of Chicago online has all the details you need.

September 9: The 23rd Annual PAWS Chicago 5K

PAWS Chicago 5K - Photo by Brian Hlavacek (1)
Photo by Brian Hlavacek

Ready. Set. Bark! Bring your furry friend over to Montrose Harbor for the animal-friendly 23rd Annual PAWS Chicago 5k. The race is in support of making Chicago a no-kill city and helping homeless pets get a second chance. After the run, participants — both human and canine — are welcome to share in the lineup of fun for the afternoon, including: live entertainment, an interactive dog agility course, raffles and a whole lot more! Specifics about the race and registration are available on the PAWS Chicago website.

Montrose Harbor, Grove 16

September 9: Vintage Car Show

For car lovers, nothing beats a hot summer day where one can view polished classic cars as far as the eye can see. From vintage models to unique classics, muscle cars to hot rods and more, browse the variety at this free event, open to all ages — complete with live music, tasty bites and cool beverages. Plan your visit by checking out the Enjoy Highland Park website.

The Lot, 525 Central, Highland Park

September 9-10: Printers Row Lit Fest

Photo by Ken Carl

A long-standing, end-of-summer tradition in the South Loop is the Printers Row Lit Fest, this year celebrating its 38th anniversary. Endless tents and tables of literary finds sprawl across five blocks in addition to stages which will feature readings from authors, discussions, programming for kids and more. This family- and community-friendly series is free, and encourages people to come and go as they please. More details about the fest and its history are available in Better’s previous content; or visit the Printers Row Lit Fest.

From Dearborn St. to Ida B. Wells Dr.

September 9-10: Lakeview East Festival of the Arts

All over the city there are art and music festivals, but can you ever really get enough? Head on over to the Lakeview East and check out over 150 juried artists who will be displaying world-class art in a number of mediums, like painting, sculpture, jewelry, photography and more. Additionally, there will be multiple stages with live music, kids activities and, of course, wine, beer and food booths. Hours vary per day, more information can be found on the Lakeview East Festival Of The Arts website.

Along Broadway, Belmont to Hawthorne

September 10: Run for the Parks!

Chicago proudly supports its beloved park system, and if you want to be a part of that support too, then check out the upcoming Run for the Parks! 5K. The race — which is sponsored by Chicago Parks Foundation and encourages running, walking or rolling — will take place along the picturesque Lakefront Trail. Afterwards, enjoy a pancake breakfast, live DJ, refreshments and some community fun! All are welcome, secure your spot on the Run for the Parks! site.

3155 S Lake Shore Dr.

September 15-17: Riot Fest

Since 2015, Riot Fest has been rocking stages in Douglass Park with some of rock music’s grittiest, alternative, fan-loved bands. This year’s line-up boasts names like Foo Fighters, The Cure and many other classics of the genre. While dedicated fans may have already nabbed their tickets, there are still daily and weekend passes available to one of Chicago’s newer, favorite concert series. Additional information and tickets can be found on the Riot Fest website.

1401 S. Sacramento Dr.

September 15-17: Norwood Park Fall Fest

Unsure when to make that transition from summer to fall? Let the Norwood Park Fall Fest help you, with a weekend they describe as a “fall-themed haven” for delicious local food; tasty beer and beverages; live music with a range of genres; a children’s area with live entertainment; and tons of merchandise booths with local goods. Whether or not you’re ready for autumn, come share in this community fun! There is a $5 recommended donation for entry; this is a family-friendly event. More information is available on the Fall Fest site.

Northwest Highway (between Raven & Newark) and Centennial Park, Norwood

September 16-17: Ravenswood ArtWalk

In its 21st year, the Ravenswood ArtWalk (RAW) will be honoring its theme — “Tour of Arts and Industry” — with a weekend-long celebration of the local creative community. Guests can expect to see open studios and galleries; pop-up performances; and an outdoor arts market with 50+ local makers; live music and dance; food vendors; and a Malt Row beer garden. This family-friendly event is the perfect chance to take in a bit of the culture you may not otherwise have the chance to. Get all info at Ravenswood ArtWalk online. 

Ravenswood Industrial Corridor, Lawrence to Irving Park Rd

September 20: Forever Summer at LH Rooftop, LondonHouse Chicago

LondonHouse Chicago

Endless summer vibes await at the LH Rooftop of LondonHouse Chicago on Wednesday, September 20. Dive into “Forever Summer,” a day-long celebration from 11 AM till close, where the skyline views are just as breathtaking as the festivities. Start with a 25% off lunch (11 AM-2 PM) before toasting with passed Veuve Champagne at 5 PM. With all-day drink specials, live DJs setting the mood, and exclusive swag bag giveaways, summer might be ending, this should help take out the sting.

LondonHouse Chicago, 85 East Wacker Drive At North Michigan Avenue

September 21-24: Chicago Gourmet

If you, like many other Chicagoans, love the diverse, delicious food our city has to offer then you need to grab your ticket for Chicago Gourmet this month. The four-day event at various locations features a lineup of curated chefs and their expertly-crafted bites — including, Tacos & Tequila; Somm Sessions; Hamburger Hop; Late Night Gourmet; Grand Cru; Rise & Shine Gourmet; Prost! In the Park. This event is 21+ and recommended as an outing for friends or couples, but not for kids. Nab your ticket while you still can at Chicago Gourmet.

September 22-23: 312 Block Party

Goose Island may be known for their delicious beer, but how about block parties? This year they are back again, putting themselves to the test with the 312 Block Party, which will feature live music and plenty of oh so delicious brews on tap. Beer drinkers and local brewery lovers, this one’s for you! Purchase your ticket on the 312 Block Party site, and see the lineup — of both musicians and beverages — they have in store this year.

1800 W. Fulton St.

September 23: Beverly Art Walk

Throughout the Beverly and Morgan Park neighborhoods this month, you may find yourself at the Beverly Art Walk. This year’s event — held at various locations — will feature a lineup of over 150 artists exhibiting their works in shops, studios, bars, galleries and more. What’s more, there will be artist demonstrations, performances, art installations, live music and an exhibition of street art at the Beverly Arts Center curated by Won Kim, a local artist, chef and DJ. Visit Beverly Art Walk online for more specifics.

September 23: Chicago Water Lantern Festival

The Water Lantern Festival “is filled with fun, happiness, hope and great memories that you’ll cherish for a lifetime,” say the hosts of the event. And they’re not wrong, neither are the countless folks who turn up to Humboldt Park for the annual celebration. All are welcome to this unique event that is known for being family friendly. Visit the Water Lantern Festival online for details and early bird prices.

1400 N. Humboldt Dr.

September 23-24: Hyde Park Jazz Festival

Well-loved by jazz heads from near and far, the 17th annual Hyde Park Jazz Festival is back for another music-packed year. With over 30 acts ready to take the stage, attendees who range from devote jazz lovers to newbies of the genre will find something to love. More information on this celebration of all things jazz can be found on the festival website.

Venues across Hyde Park

September 23 & 27: The Flying Dutchman

For a limited run this month — and with select dates in October — the Lyric Opera in Chicago will be premiering Wagner’s The Flying Dutchman. The story follows a young woman’s obsession with the Dutchman, who’s cursed to wander the earth, only coming ashore every seven years in search of a woman who will be faithful to him until death. Watch the age-old tale unfold on one of Chicago’s favorite stages — reserve your tickets now while you still can at the Lyric Opera online.

20 N. Wacker Dr.

September 23 & 30: Barktoberfest at Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk, in collaboration with Pup’s Pet Club, presents Barktoberfest along the scenic Riverwalk. From 11 AM – 4 PM, visit the vibrant market where local pet businesses showcase their products and offer engaging, dog-centric activities to attendees. It’s a pup’s paradise with the chance to socialize, shop, and even indulge in the specially curated pup menu from the Chicago Burger Company. Choices include the tempting Barkuterie Board, Bark Burger, Cookie Treat, or Pup Cup. Don’t miss out on this tail-wagging event.

301 E North Water St.

September 28: The Walk with Little Amal 

Photo by Igor Emerich

Chicago Shakespeare Theater welcomes The Walk with Little Amal in partnership with Navy Pier, featuring Uniting VoicesA.B.L.E., Chicago Children’s Museum, and the Syrian Community Network. The 12-foot-tall puppet of a Syrian refugee child will make her first Chicago appearance at the Theater on September 28 as part of her journey across the United States. 

September 28-30: 6th Chicago International Latino Theater Festival

6th Chicago International Latino Theater Festival returns to Chicago again this year as the citywide festival showcasing local, national and international Latino theater artists and companies. The festival kicks off at the end of September but has an impressive run that lasts until November 12. The festival lineup includes 17 productions new to the city and remains a “cultural high point of Chicago’s Latino Heritage Month.” Find more details on the Chicago International Latino Theater Festival site.

September 30: AIDS Run & Walk Chicago

Since it began in 2001, nearly 25,000 participants have come together for the AIDS Run & Walk Chicago, raising $6 million to battle the HIV epidemic. While raising awareness and funds for AIDS Foundation Chicago and partners — with proceeds directly benefiting programs and services that improve people’s lives — the race is also an excellent way to get out and spend time with the community. AIDS Run & Walk Chicago online has all the race details you need as well as virtual registration. Your support could make a difference for countless people near and far!

Soldier Field, 1410 Special Olympics Dr.

September 30: Taylor Swift Bar Crawl

Hey T-Swift fans! If you want to hit the town while celebrating the best tracks of your favorite artist, then the Taylor Swift Bar Crawl is exactly where you need to be this month. By purchasing a ticket you are guaranteed admission to all bars on the crawl; a free brunch buffet; gift cards to use on the crawl; Taylor themed drink specials; giveaways; an after party; and enough Taylor Swift music to satisfy even the most dedicated of fans. What are you waiting for? Reserve your tickets online now.

More from Better:

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.