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Things to Do in Chicago in September (2022)

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This post covers the best things to do in Chicago this September including free events, family-friendly activities and things to do at night, updated for 2022.


Chicago is a lovely place to visit in September.

Check out the suggestions below for a variety of activities, including sports, theatre, music, and of course, seasonal festivals.

For some of the more popular things to do in Chicago, read the following posts:

Some of the things we’ve listed here are included in one of the available tourist attraction discount passes.

Tourist Passes Reviewed

1. Go to a Sporting Event

There are plenty of sports events in September.  You've got football, baseball, women’s basketball, and soccer. More details about Chicago teams are below the video.

If you are looking for evening plans, seeing a game is an option. For more things to do at night, check the section on nighttime activities below.

Fun fact: Softball was invented in Chicago in 1887 on Thanksgiving Day!

2. Go on a Sightseeing Tour

There isn’t a better way to experience a city than on foot with one of our history-loving Chicago-adoring tour guides!

We offer pay-what-you-like walking tours multiple times each week.

If you’d prefer to enjoy a bus tour, we have a read our comparison post of Chicago’s best bus tours

Another way to see the Chicago River on an architecture-focused river cruise.

3. Go to a Stand-Up Comedy Show

There are several stand-up performances scheduled for September of 2022.

Here are just some of the great shows playing this month.  

TIP: Check out our self-guided theatre tour to admire the exterior of some of the oldest movie palaces in the Loop.

4. Go to a Concert

If you are a music lover or a fan, be sure to check out a concert while in Chicago.  There are many venues from giant spaces to intimate bars.  

Below we list a few of Chicago's best music venues to check out.

5. Chicago Jazz Fest

Join the rest of the foot-tapping crowd in Millennium Park throughout September to enjoy Chicago’s annual free Jazz Festival.

There will be many local artists and some guests as well. Either get there early to snag an up-close seat or bring a blanket and a picnic lunch to enjoy in the lawn space.

This is a free festival and family-friendly! Get more details are here.

TIP: Learn more about Millennium Park on our Pay-What-You-Like walking tour of the Loop & Millennium Park.

Or if you prefer to move at your own pace, use our self-guided Millennium Park Tour.


Eat, drink, and be merry!  You can’t miss the beginning of Oktoberfest in Chicago (September 9th - 11th, 2022). 

Head to Lincoln Square for the opening ceremony at 8 pm on Friday. 

For beer-connoisseurs, see our post where to find Chicago's best craft beer

7. Stroll the Riverwalk

September's comfortable weather is ideal for exploring the Riverwalk.

This beautiful stretch will bring you below the busy streets and right along the river’s edge, lined with restaurants, art, and fountains.

Learn more about the river and the riverwalk itself on our Riverwalk and History Tour.

8.  Take a Boat Tour

September weather is quite nice to enjoy the views of the city from a boat. There are all kinds of ways you can get out on the water in Chicago.

There are architecture cruises, sightseeing tours, speedboats, sailboats, kayaks, and water taxis.

See our comparison post of Chicago’s best boat tours to find out what options you have. 

TIP: Many tourist passes include a boat ride or cruise. If you want to save some money, consider getting a tourist pass if you plan on taking a cruise in addition to other top activities in Chicago. 

9. Attend a September Festival

There is always a fun festival to attend when the weather is nice in the Windy City. Below we've listed a handful of festivals that are free, family-friendly, or just plain fun.

These festivals take place all over the city, so why not learn more about the neighborhood on one of our pay-what-you-wish walking tours or our self-guided tours

For even more festivals, check out Choose Chicago for a full event calendar.

10. Save Money with a Chicago Tourist Pass

Many of Chicago’s biggest attractions have entry fees. While you do pay for a tourist discount pass, it can give you a bulk discount and free admission into some interesting tours and museums, saving you up to 55%.

They can also save you time with skip-the-ticket-line privileges at select attractions.

Each Chicago Tourist Discount Pass includes a variety of fun family-friendly activities and attractions.

Here are a few examples of what you can visit with a tourist pass, for a discount or for free.

Chicago Travel Tips and Hacks

For more details, make sure to read our full post covering Chicago tourist passes.


There are many free activities to take advantage of in Chicago including some we have mentioned some above like taking a pay-what-you-like walking tour, hearing live jazz in the park, or attending a festival.

Check out our comprehensive post about the Top Free Things to Do in Chicago.

Movies in the Park

For the past 20 years, Chicago’s Movies in the Park series has been lighting up the skies with free film screenings.

Parks dotted all across the city will be showing recent films, and along with some classics.

Check out the schedule here.

World Music Festival 

This year would be the 43th Annual World Music Festival Chicago.

This city-wide, multi-venue festival is perfect for music lovers and artists! 

It has a unique blend of different countries and cultures which makes it a great experience for locals and visitors.

The festival takes place from September 30th to October 30th, 2022.

Under the Picasso

There are many free events at Daley Plaza throughout the year by the Picasso Statue.

Most often the events include music, dance, or public art. Look at the upcoming calendar to see what events are scheduled.  

TIP: Our Loop & Millennium Park Tour goes through Daley Plaza!

Mexican Independence Day Parades

You'll have two chances to enjoy a Mexican Independence Day Parade in September. These parades will be musical, colorful, and festive. 

These make for a great family-friendly activity! You can find more family events below.

TIP: To find some of the best Mexican food in Chicago, try our Self-Guided Mexican Pilsen Food Tour.

Free Museum Day

On September 17th, 2022, many top museums in Chicago are offering free admission for two people.

Find out all the museums that participate at the official website for Museum Day Live

If you arent here on that date, don't despair. There are some museums in the city that are always free and others that are sometimes free. 

See our post on free museums to find out more.

Von Steuben German Parade 

This German parade on September 10th at 2 pm honors Baron Friedrich von Steuben, who came to America to assist General George Washington. 

This fun and celebratory parade will have many participants who dance and play music.

Located in the German neighborhood of Lincoln Square, this parade leads to the annual Oktoberfest. (See German)

This year is also the 100th Anniversary of the German-American Day Festival which runs from September 9th - 11th, 2022.

Check out the Chicago Cultural Center

This beautiful and historic building is free and open for the public to explore.

Beyond the art that lines the walls, you will find free traveling films, lectures, and performances here. 

This is also a great place for children’s programming. 

Check out their calendar of events to see what is going on during your visit.

Explore the Farmers Market

Enjoy local produce before the summer ends! From tasty veggies to locally made jams to homemade crafts and baked goods, you will definitely find something interesting or delicious.

Markets are open almost every day of the week on Tuesdays, Wednesdays, Thursdays, Saturdays, and Sundays.

Find a list of the city’s markets and their schedules here.

For even more free activities, see our post on the top free things to do in Chicago.


Many of our top ten activities are perfect for the evening hours, such as seeing a sporting event, going to the theater or attending a concert.

Below are some more ideas. Be sure to read our post about the top things to do in Chicago at night for even more suggestions.

Take a Night Tour

Looking to see a different side of Chicago? Take a walk with some spooky history on our evening Ghost Tour.  

You can expect to laugh more than you scream as you learn about past hauntings. You will also learn some of the dark history of The White City.

For a lovely view, check out our  Twilight Chicago Riverwalk & History Tour which ends a 10-minute walk from Navy Pier.  

Also, several bus tours operate night versions of their day tours.

LGBTQ+ International Film Festival

The Cultural Center hosts the LGBTQ+ International Film Festival on September 22nd - October 2, 2022

This year they are celebrating their 40th anniversary!

Chicago Horror Film Fest

Join the other horror film fans at the Chicago Cultural Center to indulge in spooky movies!

The 23rd annual Chicago Horror Film Festival takes place from September 24th - 25th.

See an Improv Show

Chicago is well known for comedy and improv. Just ask Tina Fey, Amy Poehler, or Steve Carell.

Below are just a few places to catch an evening show.  

You may be seeing seasoned Chicago improvisers or you might catch a group of students, but who knows? One of them could be the next Chris Farley.

Take in the Local Music Scene

There are plenty of local musical experiences at night.  If you’re looking for even more opportunities to check out the local music scene, take a look at some of the more popular venues:

Admire Art at the Mart

While strolling along the Riverwalk in the evening, be sure to walk along the south side of the Chicago River so that you can see a newer art installation called “Art of the Mart”.  

It is a series of non-sponsored projections on the side of a historic Chicago building called the Merchandise Mart. 

Find out more from their website, Art at the Mart.

Go to a Game Bar

Whether you want to try an arcade bar with some pinball and Pac-man or try a classic board game, Chicago has a game bar for you.

Check out our favorite game bars across the city.

Batting Cages

Practice your baseball skills right outside of historic Wrigley Field at the batting cages at Sluggers.

Beyond the batting cages, you can participate in other games such as skee-ball, and catch some games on the TVs at this beloved sports bar.

Go Out for a Cocktail

Chicago has speakeasies – fitting for the mobster history of the Windy City, some of the Best Rooftop Bars.

In our Guide to Chicago Bars you can find out about historic bars, game bars and where to have a pint while playing some trivia.

If you’re looking for more than just atmosphere and want to find one of the best Craft Beers, we can make sure you find a local pint.

Be sure to check out our post on top things to do in Chicago at night for even more suggestions.


Throughout this post, we have listed several activities that are suitable for kids, such as seeing an outdoor movie, going to a sports game, or seeing a musical. 

Below you will find several great options to keep your children entertained this month, including parks, museums, and theater!

Be sure to check out our post about family-friendly activities in Chicago for a more complete guide.

Check Out a Museum

In September, local kids are back in school which means fewer crowds at the children's museums!

Chicago's museums are very interactive and ideal for kids. The number one choice is the Children’s Museum (see the video above).

Also, try the Peggy Notebaert Nature Museum, a lovely nature museum with many kid-friendly events.  Check their special event calendar to see what is happening throughout the summer!

Other museums that are enjoyable to kids are The Field Museum and Museum of Science and Industry.

Go to a Baseball Game

We have two baseball teams here, so there are plenty of options for families to go catch a game!

The Cubs play north of downtown at Wrigley Field, and the White Sox play south of the skyscrapers at the Guaranteed Rate Field.

Tour both stadiums, or just enjoy the fresh air while cheering on our Chicago teams!

Children’s Theatre

Check out a family-friendly kid show with Emerald City Theatre or Chicago’s Children Theatre.

Both are well known for wonderful family programming. 

Check their websites for updated show schedules and ticket information.

Spend the Night at Museum

Many of the museums offer special events where the kids can spend the night amongst the exhibits - whether it is dinosaurs or butterflies depends on the museum.

They offer kid friendly activities and tours of the museums and an unforgettable way to experience some of the iconic sites of Chicago.

Visit the Shedd

Head to the Shedd Aquarium with your little ones

You can wander around and view the aquatic wildlife that live at the zoo.

There's also a 4-D Experience covering sharks, one covering the Octopus, and a third covering Spalsh and Bubbles, some very colorful fish.

You can also book a guided tour or book a private meeting with a Beluga Whale or some penguins!

Visit the Shedd's website for more information.

Go to the Zoo

The Lincoln Park Zoo is one of the oldest zoos in the country, and one of the last few free zoos.

Home to over 1,000 animals, this is a great stop during your time in the city.

While you are in the area, you can also explore the Lincoln Park Conservatory and the park itself.

Play in a Park

Chicago is full of green grass and playgrounds for kids to get out their energy.

One of the best parks, Maggie Daley Park, is nestled between downtown and Lake Michigan. It has lots of different playgrounds for kids of all ages, a rock climbing wall, mini-golf, and tennis courts.

Find out about this park and more by reading our post, Chicago's Beautiful Parks.

See our post about family-friendly activities in Chicago for even more great things to do.

About The Author


Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!
Updated: September 21st, 2022
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