Best Things to Do in Chicago in September

Looking for what to do in Chicago this September? Here are the best things to do in Chicago in September (from a local).

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.

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

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Take an Architecture Cruise

Taking an architecture river cruise is a must when visiting Chicago.  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

skyline from lake cruise in Chicago in the summer
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. If your time is short, you can do a combination river and lake cruise. Lake cruises depart from Navy Pier or the Michigan Avenue bridge.


Take a Kayak Tour

September tends to be the month with the best weather in Chicago, making it a great time for kayaking. Taking a guided kayaking tour in the Chicago River is great way to explore the city.

If you are an experienced kayaker, you can rent a kayak on the Chicago River or Lake Michigan.

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

Moose Bubblegum Bubble by Jacob Watts one of the most famous street art murals in Chicago

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.

Other neighborhoods that have a high concentration of street art include Pilsen as well as West Town.

Walk or Bike the Lakefront Trail

Chicago lakefront

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.

Listen to Free Music at Millennium Park

One of the best things to do in Chicago is listening to free concerts at the Jay Pritzker Pavilion in Millennium Park.

The Millennium Park Summer Music Series will feature a wide variety of genre-defying music from established and emerging artists on Mondays and Thursdays from 6:30–8:30pm until September 16, 2021.

The new Chicago In Tune festival will present new and reimagined programs in place of this year’s Gospel music, Jazz, House, and Blues festivals in Millennium Park. Four special evenings at Jay Pritzker Pavilion will honor music born and innovated in Chicago, presented by the Millennium Park Foundation, on the following dates and times:

Gospel: Friday, September 3, 5:30–8:30pm
Jazz: Saturday, September 4, 5:30–8:30pm
House: Saturday, September 11, 5:30–8:30pm
Blues: Saturday, September 18, 5:30–8:30pm

Go to a Baseball Game

what to see in Chicago

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

best things to do chicago travel blog

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.

Hang Fun at Navy Pier

rides at Navy Pier Chicago
Navy Pier can be somewhat of a tourist trap but it is a must do if you are visiting Chicago with toddlers or kids. Fun attractions include a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line), rides and games, restaurants, shops and the Chicago Children’s Museum.

Navy Pier will have a free fireworks show on select Saturday nights in September (09:30p.m.-09:40p.m. on September 11 and 18, 2021).

Navy Pier is also the starting point for many boat rides and lake cruises.


Watch Fireworks

Navy Pier puts on free fireworks shows in the summer but they have extended their fireworks show into September this year. You don’t have to visit Navy Pier to enjoy the fireworks, you can see them from the lakefront and various restaurants. You can also see fireworks from the water on fireworks lake cruises.

When: September 11 and 18, 2021 from 09:30-09:40 p.m.


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.

Where: 875 North Michigan Avenue, 94th floor, Chicago, IL 60611

Cost:  $25 for adults, $15 youth.


See the Immersive Van Gogh Exhibit

From the creators of the blockbuster show at Atelier des Lumières seen by over 2 million visitors in Paris and Toronto and featured in Emily in Paris (one of my favorite travel shows on Netflix), the Immersive Van Gogh Exhibit, is a massive indoor digital presentation of Vincent Van Gogh’s artwork. Tickets must be purchased online in advance and they are selling quickly! There are also yoga sessions which include a 35 minute Yoga class + 45 minutes thereafter to enjoy the exhibit.

Where: Lighthouse ArtSpace at Germania Place, 108 W. Germania Pl, Chicago, IL

Cost:  Tickets start at $39.99 plus fees for off peak times. See https://www.vangoghchicago.com/ for full prices and to purchase tickets in advance.

See the Water Displays at Buckingham Fountain

Buckingham Fountain is a must see Chicago attraction in September
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 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.

Watch Free Movies in the Park

You can watch free movies in various Chicago public parks until September 14, 2021. The annual Movies in the Parks series brings Hollywood movies and local films to local parks- from classics and retro childhood favorites to the best family-friendly box office favorites from recent years. Movies start at dusk.

Walk Through a Sunflower Field

Visiting sunflower fields was a popular activity for Chicagoans this summer. Many sunflower fields and mazes are still in bloom and open for visitors in September. Here is a list of the best sunflower fields near Chicago with locations, dates, hours, prices and all the information you need to plan your visit.

Go Apple Picking

Looking for a fun outdoor activity in the Chicago area? Take a day trip to a nearby apple orchard to go apple picking or indulge in fresh apple cider donuts. There are many apple orchards are located in the Chicago suburbs about an hour or less from downtown. Some apple orchards also offer kid friendly attractions and activities like pumpkin patches, corn mazes, kid farms and more.

September is apple picking season but different types of apples are available for picking throughout the month.  Here is a list of the best apple orchards near Chicago for apple picking with locations, dates, hours, prices and all the information you need to plan your visit.

Sundays on State

Chicago Theatre instagram photo spot

In an effort to bring people safely back to the Loop, Chicago Loop Alliance will transform State Street from Madison to Lake into an open street on select Sundays. This portion of the street will be closed to vehicle traffic for a free, interactive block party to give pedestrians a chance to experience arts and culture, active recreation, retail, restaurants, and bars against the backdrop of State Street’s iconic architecture like the Chicago Theatre (one of the best Chicago photo spots).

Where: State Street from Madison to Lake

When: September 5 and 12 from 11 a.m.-8 p.m. Click here for more information.

Other September Events

Many music, food and other outdoor festivals and events take place in Chicago in September. Some festivals are very well known and attract thousands of tourists, but there are many smaller outdoor festivals and events in Chicago where you will mostly find locals. Festivals and events scheduled for this September include:
Roscoe Village Burger Fest (September 4-5, 2021), ARC Music Festival (September 4-5, 2021), Pitchfork Music Film Series (September 6-8, 2021), Pitchfork Music Festival (September 10-12, 2021), Lincoln Park Greek Fest (September 10-12, 2021), German-American Oktoberfest (September 10-12, 2021), Chicago Vegandale (September 11, 2021), Printers Row Lit Fest (September 11-12, 2021), Riot Fest (September 17–19, 2021), Fall Fest Norwood Park (September 17–18, 2021), Craft Brews at Lincoln Park Zoo (September 18, 2021), Fall Nature Fest @ LaBagh Woods (September 18, 2021), Run Your Sox Off (September 18, 2021), Lakeview Taco Fest (September 18-19, 2021), Renegade Craft Fair (September 18-19, 2021), Artfest Michigan Avenue (September 18-19, 2021), West Loop Art Fest (September 18-19, 2021), Oktoberfest Chicago (September 24-26, 2021), Hyde Park Jazz Festival (September 25-26, 2021) and Chicago Gourmetthings to do in Chicago in September.

Planning a trip to Chicago? Check out my Chicago guides and itineraries:



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