BEST Things to Do in Chicago in September (From a Local!)

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. Although Labor Day weekend is considered the end of summer, there are still plenty of events and festivals that take place in 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.

I suggest bookmarking this blog post as I will be updating it regularly with new events and activities.

Things to Do in Chicago in September

Below are the top things to do in Chicago in September including all of the best September festivals and events.

Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.

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

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.

Listen to Concerts Under The Stars

Enjoy classical music concerts on a rooftop before the temperature gets too cold to be outside. Upcoming Concerts Under The Stars this September include:

Sinatra Under the Stars at AIRE

You can find the full list of Concerts Under The Stars here.

Attend a Candlelight Concert

Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Some of the concerts taking place this September include:

Candlelight: A Tribute to Bad Bunny
Candlelight: A Tribute to Adele
Candlelight: A Tribute to Juan Gabriel
Candlelight: The Best of Hans Zimmer at Music Box Theatre

You can find the full list of candlelight concerts in Chicago here.

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.

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

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 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.

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.

Watch Classic Movies on a Rooftop

Watch classic movies against the backdrop of the Chicago skyline with Rooftop Cinema Club, an outdoor screening series on a rooftop located on the fifth floor terrace of The Emily Hotel (311 N Morgan St) in Fulton Market. Rooftop Cinema Club is a high end movie experience complete with tropical decor, lawn games, state-of-the-art LED screens, individual wireless headphones and a range of seating options including lounge chairs and loveseats. Guests can also order drinks and snacks. You can purchase tickets in advance here.

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.

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 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.

Attend an Outdoor Festival

Many music, art, food and other outdoor festivals take place in Chicago in September. 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. Outdoor festivals scheduled for September include: Chicago Jazz Festival, North Coast Music Festival, ARC Music Festival (September 1, 2024), Taste of Polonia Festival (September 1-2, 2024), Throwback Music Fest , German-American Fest, Riot Fest, Edgewater Arts Festival, Hyde Park Jazz Festival, Oktoberfest at St. Alphonsus and Lincoln Square Ravenswood Apple Fest.

More Chicago September Events

In addition to the festivals mentioned above, other Chicago September events include: Fifth Third Bike the Drive, Printers Row Lit Fest, 26th Street Mexican Independence Day Parade, Chicago Gourmet and Beverly Art Walk.

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:



Leave a Reply

Your email address will not be published. Required fields are marked *

CommentLuv badge

This site uses Akismet to reduce spam. Learn how your comment data is processed.