Looking for what to do in Chicago this September? Here are the best things to do in Chicago in September 2025 including all of the best September 2025 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 2025
Below are the top things to do in Chicago in September 2025 including all of the best September 2025 festivals and events.
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 2025 including: Taste of Polonia Festival (August 29-September 1, 2025), German-American Fest (September 5-7, 2025), Norwood Park Fall Fest (September 12–13, 2025) and Riot Fest (September 19-21, 2025).
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.
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.
Check out the new Flyover Chicago, an immersive flyover experience.
Other fun attractions at Navy Pier including a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line), restaurants, shops and the Chicago Children’s Museum.
In addition to Navy Pier’s attractions, visitors can enjoy free events and programs including Live on the Lake!, an outdoor live music series ending in September.
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.
See the Water Displays at Buckingham Fountain
Buckingham Fountain, a well known Chicago landmark in the center of Grant Park, is one of the largest fountains in the world. The water will be turned off for the season in October (depending on weather) and will not be turned back on until May. When the water is turned on, it produces a major water display for 20 minutes every hour with a center jet shoots water to a height of 150 feet into the air. Beginning at dusk, a spectacular light and music display accompanies the major water display.
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.
More Chicago September 2025 Events
In addition to the festivals mentioned above, other Chicago September 2025 events include: Renegade Craft Fair (September 6-7, 2025), Chicago Gourmet (September 25-28, 2025) and Randolph Street Market Festival (September 27-28, 2025).
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:
