Looking for what to do in Chicago this September? Here are the best things to do in Chicago in September 2026 including all of the best September 2026 festivals and events.
I suggest bookmarking this blog post as I will be updating it regularly with new events and activities.
Chicago in September
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September is usually a great month to visit Chicago. I consider September to be the month with the best weather – temperatures are still usually warm so you can enjoy most of the same outdoor activities that you can in the summer without the crowds. Although Labor Day weekend is considered the end of summer, there are still plenty of outdoor events and festivals that take place the entire month of September.
For out of town visitors, please note that the weather in Chicago is very unpredictable and temperatures can vary greatly. Be prepared for both hot summer temperatures and fall temperatures as well as rain. Make sure to pack a travel umbrella, layers and check the weather right before your visit to know what to expect.
Things to Do in Chicago in September 2026
Below are the top things to do in Chicago in September 2026 including all of the best September 2026 festivals and events.
See the Last Summer Fireworks Show at Navy Pier
See the last free fireworks show of the summer season at Navy Pier on Saturday, September 5, 2026 at 10pm.
While you can watch the fireworks show from Navy Pier, you can also watch it from various spots along the Lakefront.
The most relaxing way to watch the fireworks is a fireworks lake or river cruise which will stop on the water for passengers to enjoy the show.
Balloon Museum’s EmotionAir Exhibition
Balloon Museum’s EmotionAir Exhibition is a limited time unique exhibition that explores the profound relationship between art and emotions through the captivating medium of inflatable art. This exhibition, first presented in London in December 2023, is committed to the work of emotions, transforming artworks into mirrors to explore the profound relationship between art and emotions, action, and reaction. This is manifested tangibly through Inflatable Art, which offers itself as a medium to express the most intimate nuances of human feelings. Through a mix of interactive installations, emotional projections, and performance art, EmotionAir aims to transport visitors on an unprecedented sensory journey.
When: Extended through September 7, 2026
Where: The Fields Studios – Gate 1, 2828 N. Pulaski, Chicago, IL 60641
Cost: Timed-entry tickets are required. Click here to purchase tickets.
Drunk Dracula
Step into a darkly enchanting adult-only adventure at Drunk Dracula where laughter, tipsy thrills, and the legend of Dracula collide. Each 90-minute session invites you to sip, shiver, and revel in the mischievous antics of a vampire gone delightfully rogue. Mingle with fellow thrill-seekers in a mysterious, adult-only setting. Must be 21+ with valid ID.
When: Opens September 17, 2026
Where: 182 North Wabash Avenue, Chicago, IL 60601
Cost: Prices start at $29 per person. Click here to purchase tickets.
Attend a Candlelight Concert
Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful indoor venues bathed in candlelight. Some of the concerts taking place this September include:
Tribute to Juan Gabriel on Strings
Tribute to TOOL
You can find the full list of candlelight concerts in Chicago here.
Take an Architecture River Cruise
Taking an architecture river cruise is a must on any Chicago bucket list. While you can go on an architecture cruise most of the year (except when the water is frozen), they tend to be less crowded and the weather tends to be more pleasant in September.
Take a Lake Cruise
If you enjoy being on the water, a lake cruise is also a fun activity. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views especially around sunset. Lake cruises depart from Navy Pier or the Michigan Avenue bridge.
If your time is short, you can do a combination river and lake cruise.
Go Kayaking in the River or Lake
A fun way to enjoy city views is to go kayaking in the Chicago River or in Lake Michigan. You can rent a kayak in the Chicago River here and Ohio beach here.
You can also join a guided kayaking tour in the downtown portion of the Chicago River including this history and architecture kayak tour and this sunset kayak tour.
Please note that you will get a little wet when kayaking so bring a waterproof case for your phone and water-resistant or quick-drying clothing.
Look for Street Art
September is a great month to walk around Chicago looking for street art.
One of the most well known Chicago murals is “Moose Bubblegum Bubble” by Jacob Watts which located at 33 E. Congress (South Wall). This famous mural is part of the Wabash Arts Corridor and is walking distance to Millennium Park, The Art Institute of Chicago and other well known tourist attractions.
Another famous mural is the Greetings From Chicago Mural at 2226 N Milwaukee Ave. You can see this mural and other street art on this street art tour.
Have Fun at Navy Pier
Navy Pier is a must do if you are visiting Chicago with toddlers or young kids.
Ride the large Ferris wheel (click here to purchase a fast pass ticket and skip the long line).
Other fun attractions at Navy Pier include Flyover in Chicago, an immersive flyover experience, the Chicago Children’s Museum, rides and games and several restaurants, bars and shops.
In addition to Navy Pier’s attractions, visitors can enjoy Live on the Lake!, an outdoor live music series through September 7, 2026.
Enjoy the Views from 360 CHICAGO Observation Deck
360 CHICAGO, the observatory on the 94th floor of the former John Hancock Building, has one of the best views of the Chicago skyline and Lake Michigan. (Click here to buy a skip the line ticket).
Where: 875 North Michigan Avenue, 94th floor, Chicago, IL 60611
Walk or Bike the Lakefront Trail
Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan. When the weather is nice and especially on weekends, the lakefront is packed with locals and visitors walking, running and riding bikes. Walking or biking all or part of the trail is a great way to see Chicago skyline, people watch and get some exercise. Here is a map of the trail as well as its access points.
See Famous Works of Art at the Art Institute of Chicago
Want to escape the heat and head indoors to cool off? The Art Institute of Chicago (111 S Michigan Ave) is one of best indoor attractions in Chicago. It is one of the largest art museums in the United States and is frequently found on lists of the top museums in the world. You must purchase your ticket online in advance.
Click here to buy a fast pass ticket if you want to avoid long lines.
Go to a Baseball Game
September is the last full month of the regular baseball season. Whether a fan of the Cubs, baseball in general or just a fun atmosphere, a day at historic Wrigley Field is a must for locals and tourists alike. You don’t need to enjoy baseball to enjoy a Cubs game – it is fun to just soak in the atmosphere.
When: You can buy tickets and see the Cubs schedule here. If you prefer the White Sox you can find their schedule and buy tickets here.
Hang Out on the Riverwalk
The Chicago Riverwalk is one of the best spots in Chicago for people watching and there are also restaurants, bars, shops and places to sit along the way. September is a great time to visit the Riverwalk as it is less crowded than during the summer.
Where: Along the south bank of the Chicago River in downtown Chicago from Lake Michigan to west of Franklin Street. You can see a map here.
Hours: Open daily from 6 a.m. to 11 p.m.
Visit Local Farmers Markets
September is a good month to visit farmers markets around Chicago. These markets are a great place to buy healthy, local, farm-fresh foods.
Some of the best farmers markets in Chicago include the Green City Market, the Logan Square Farmers Market and the Wicker Park Farmers Market.
Attend an Outdoor Festival
Some festivals are very well known and attract thousands of tourists, but there are many neighborhood festivals in Chicago where you will mostly find locals. Many music, art, food and other outdoor festivals take place in Chicago in September 2026 including: Chicago Jazz Festival (September 3-6, 2026), ARC Music Festival (September 4-6, 2026), North Coast Music Festival (September 4-6, 2026), Taste of Polonia Festival (September 4-7, 2026), German-American Fest (September 11-13, 2026), Throwback Music Fest (September 11–13, 2026), El Grito (September 12-13, 2026), Printers Row Lit Fest (September 12 & 13, 2026), Riot Fest (September 18-20, 2026), Old Town Oktoberfest (September 18-20, 2026), Retro on Roscoe (September 18-20, 2026), Chicago Live! Festival (September 19 & 20, 2026), World Dumpling Fest (September 19-20, 2026), Oktoberfest at St. Alphonsus (September 25-27, 2026), WingOut Chicago (September 26-27, 2026) and Hyde Park Jazz Festival (September 26-27, 2026).
More Chicago September 2026 Events
In addition to the festivals mentioned above, other Chicago September 2026 events include: Bike the Drive (September 6, 2026), Wicker Park Fine Art Fair (September 12, 2026), Ravenswood Manor Music Crawl (September 12, 2026), Ravenswood ArtWalk (September 12-13, 2026), Renegade Craft Fair (September 12-13, 2026), Move at the Shed (September 13, 2026), Chicago Gourmet (September 24-27, 2026), Top Shelf Tequila and Whiskey Tasting Festival (September 26, 2026), Randolph Street Market Festival (September 26+27, 2026) and World Music Festival (September 25-October 4, 2026).
For more September 2026 events, bookmark this post about the best weekend events which is updated every week.
As you can see there are many things to do in Chicago in September.
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
