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 2021.
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.
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.
- Football | Chicago Bears (August - December)
- Baseball | White Sox or Cubs (April - October)
- Women’s Basketball| The Chicago Sky (May - October)
- Soccer | Fire (March - October)
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
While there are usually at least a few musicals to see in Chicago at this time of year, most of those theatrical events have been pushed to October/November.
With that being said, there are several stand-up performances scheduled for September of 2021.
Here are just some of the great shows playing this month.
- TJ Miller | Sept 9th, 10th, 11th
- Jo Koy | Sept 9th, 10th, 16th
- Terry Fator | Sept 17th
- Ron White | Sept 18th
- Mick Foley | Sept 18th
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.
- Greta Van Fleet | Sept 3rd
- Kiss | Sept 4th
- Megadeth and Lamb of God | Sept 9th
- Brad Paisley | Sept 10th
- 311 | Sept 10th
- Alanis Morissette | Sept 11th
- Jonas Brothers | Sept 12th
- Primus and Wolfmother | Sept 21st
- Harry Styles | Sept 24th
- Alice Cooper | Sept 24th
- Enrique Iglesias | Sept 30th
In addition to these concerts, there are also a handful of music festivals you may want to attend.
- North Coast Music Festival | Sept 3rd - 5th
- ARC Music Festival | Sept 4th
- Pitchfork Music Festival | Sept 10th - 12th
- Riot Fest | Sept 17th - 19th
- Chi-Town Blues Festival | Sept 18th
Below we list a few of Chicago's best music venues to check out.
5. Chicago In Tune Festival
Join the rest of the foot-tapping crowd in Millennium Park throughout September to enjoy Chicago’s annual free Jazz Festival (starts August 19th).
This event was renamed to Chicago In Tune for 2021.
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 10th - 12th).
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.
- Ravenswood Artwalk | Sept. 14-15 (Could be postponed)
- Artfest Michigan Avenue | Sept 18th - 19th
- Andersonville’s Arts Week | Sept. 19th - 22nd
- West Town Art Walk | Sept. 24th - 25th
- Chicago SummerDance | Official Dates TBD
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.
Here are a few examples of what you can visit with a tourist pass, for a discount or for free.
- Shedd Aquarium
- Skydeck Chicago
- Adler Planetarium
- Art Institute of Chicago
- The Field Museum
- Museum of Science and Industry
- 360 Chicago Observation Deck
For more details, make sure to read our full post covering Chicago tourist passes.
FREE THINGS TO DO
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 19 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.
NOTE: Dates and titles have yet to be confirmed for 2021.
World Music Festival
This year would be the 23rd 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.
NOTE: Dates for this event have yet to be announced.
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.
- 26th Street Mexican Independence Day Parade on 26th St. (Albany Ave. to Kostner)
- Pilsen Mexican Independence Day Parade on 18th Street (Newberry St. to Wolcott)
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.
NOTE: Dates for these events have yet to be determined for 2021, but there are indications that each parade will take place.
Free Museum Day
On September 18th, 2021, 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 7 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 above)
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.
Dessert Fest at the Zoo
Try out some of the best desserts in Chicago while visiting the zoo’s permanent residents.
Tickets include admission, dessert tastings, live entertainment, giveaways, and more! A portion of the proceeds benefits Lincoln Park Zoo.
Find out information and buy tickets from the Dessert Fest website.
NOTE: It has not yet been confirmed whether or not this event will take place again in 2021.
Oktoberfest on the Beach
This September, head to North Avenue beach to enjoy a beer tasting to celebrate Oktoberfest with the Shore Club.
For more information and to purchase tickets, check the website.
NOTE: Dates for this event haven't been confirmed for 2021.
LGBTQ+ International Film Festival
The Cultural Center hosts the LGBTQ+ International Film Festival on September 23rd - Oct 3rd.
Chicago Horror Film Fest
Join the other horror film fans on September 17th - Oct 1st at the Chicago Cultural Center to indulge in spooky movies!
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.
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.
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
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).
Go to a Baseball Game
We have two baseball teams here, so there are plenty of options for families to go catch a game!
Tour both stadiums, or just enjoy the fresh air while cheering on our Chicago teams!
Check their websites for updated show schedules and ticket information.
Juice Box Concerts at the Cultural Center
Head to the Cultural Center with your family of little ones every first and third Friday and Saturdays at 11:00 am-11:45 am for an engaging musical event!
While this will be enjoyable for the whole family, it is geared to kids between the ages of 1-6.
See their website for more.
NOTE: This event was cancelled for 2020 and has not yet been rescheduled.
Attend Stories, Songs and Circle Games
In September, Lurie Garden presents an interactive and free event for your little ones.
Kiddos between 4-6 will sing like sparrows and play pretend! For more details or to register, click here.
NOTE: This event has yet to be scheduled for 2021.
Events at the Library
Check out the Harold Washington Library with the kids! The children’s library is large and full of books, storytime and activities.
There are special events that range from tummy time class to crafts for toddlers.
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.