Chicago in September: 6 Things to Do and 14 Famous Events to Explore the Windy City

Summers are veritably at the apex of the tourist months in Chicago, but the time between the summer and the winter also entails quite a lot. Children are back to school, Chicagoans are gearing up their business for the fall,  the summer heat is dissipated, which means fewer crowds and ideal weather conditions calling out to the tourists all over the world! Every month in Chicago is magical and has something to offer for its tourists. But September primarily elicits music fests, concerts, culinary feasts, and more. From the boat tours to the Jazz fests, tourists can explore Chicago's rich history or enjoy the varied events with friends/family on their trip to Chicago in September!

How Is the Weather in Chicago in September?

September is the perfect month to visit Chicago as it experiences pleasant weather. With the temperature varying from 11 to 25 degrees Celsius, leaves turning amber and gold, September in the Windy City is magical. Chicago also witnesses rainfall during September, which might prolong for 7-10 days. The high point of the fall season is the celebration of Labour Day, which entails implausible events and fests that are hard to miss. With the weeks of exquisite food, art exhibits, music fests, and more, September in Chicago is the best off-season month for a trip!

6 Things to Do in Chicago in September

1. Boat Tour

Chicago looks explicable in September. Therefore, opting for a boat tour is pertinent during fall. Boat tours help you to explore Chicago in a short amount of time. From a speedboat ride to kayaking, some of the best Chicago Boat Tours include:
Tall Ship Windy - Lakeside Architectural Sail
Mercury - Urban Adventure Cruise
Wendella Boats - Chicago River Architecture Tour
Shoreline Sightseeing - Classic Lake Tour
Urban Kayaks - Historic Chicago Tour
Seadog Cruises - Lakefront Speedboat Tour
Chicago Architecture Foundation Center River Cruise

2. Riverwalk Stroll

Chicagoans and tourists love leisure walks along the riverfront, which is ideal throughout the year. There are still few attractions and boat excursions that come to life during fall, like fishing at The Jetty, as well as bird-watching with the National Audubon Society, and more!
Where: Chicago Riverwalk, Chicago, IL 60601
Open Hours: 11.00 AM to 9.00 PM

3. Are You a Sports Fan? Attend a Sporting Event

Attend a game of football, baseball, or soccer as Chicago hosts many sports events in September. It is the perfect way to spend a fun evening in Chicago.
Baseball-White Sox or Cubs (April – October)
Football- Chicago Bears (August – December)
Women’s Basketball-The Chicago Sky (May – October)
Soccer-Fire (March – October)
Soldier Field: 1410 Museum Campus Dr, Chicago, IL
Wrigley Field: 1060 W Addison St, Chicago, IL
Guaranteed Rate Field: 333 W 35th St, Chicago, IL
Buy Tickets at:

4. Immerse Yourself in a Variety of Musicals/Plays

The onset of the fall season opens the gate to various musicals and plays in Chicago in September. To name a few, the highlights here include The Lion King, Hamilton, The Book of Mormon, and more!
Cadillac Palace Theatre: 151 W Randolph St, Chicago, IL
Broadway Playhouse: 175 E Chestnut St, Chicago, IL
CIBC Theatre: 18 W Monroe St, Chicago, IL 60603
James M. Nederlander Theatre: 24 W Randolph St, Chicago, IL 60601
The Auditorium Theatre of Roosevelt University: 50 East Ida B. Wells Drive, Chicago, IL 60605

5. Sip Cocktail at the Rooftop Bars

Rooftop bars are an ideal way to spend an evening any time of the year. Chicagoans love drinking at the high above the city streets. Anyone who experiences it for the first time would love the rooftop bar the Chicago nestles. With a spectacular view of the city's skyline, these outdoor patios are perfect for a pleasant evening.
Cindy's: 12 S Michigan Ave, Chicago, IL 60603
London House Rooftop Bar: 85 East Wacker Drive At, N Michigan Ave, Chicago, IL 60601
VU Rooftop Bar: 133 E Cermak Rd, Chicago, IL 60616
The Up Room: 2018 W North Ave, Chicago, IL 60647
Devereaux: 1112 N State St, Chicago, Illinois 60610

6. Enjoy a Day of Free Admission to the Famous Museums

Throughout the year, Chicago offers free admission to the museums/zoo across the city called the Free Museum Day. Illinois Holocaust Museum & Education Center, Loyola University Museum of Art, Swedish American Museum, Clarke House Museum, National Museum of Mexican Art all offer free admission days throughout the year. 
Illinois Holocaust Museum & Education Center:9603 Woods Dr, Skokie, IL 60077
Loyola University Museum of Art:  820 N Michigan Ave, Chicago, IL 60611
Swedish American Museum: 5211 N Clark St, Chicago, IL 60640
Clarke House Museum: 1827 S Indiana Ave, Chicago, IL 60616
National Museum of Mexican Art: 1852 W 19th St, Chicago, IL 60608

Add Grandeur to Your Trip with These Chicago Events/Festivals in September

Chicago in September is flooded with events and celebrations that one would not want to skip! From the Jazz fests to food feasts, and more Chicago embraces the fall with ardor.

All about Labour Day Celebration in Chicago:

While some parts of the world celebrate Labour Day in May, Chicago commemorates it every first Monday in September. Labour Day is a federal holiday in the US hailed in reverence of the laborers' work in the development of the States. Not only does this day entail an unofficial end of the summer season, but also the onset of the fall! The fall season in Chicago brings forth many events for tourists. Hence we have penned down famous events to help you explore the city like a Chicagoan.

14 Famous Events in Chicago in September

1. Chicago Jazz Festival

The Chicago Jazz Festival is a 4-day annual fest hosted at Millennium Park. It is an admission-free fest, run by the Department of Cultural Events and Special Events in collaboration with the jazz Institute in Chicago. This fest entails performances of Jazz music by world-famous and local artists. 
Address: 78 E Washington St, Chicago, IL 60602(312) 744-3315
Where: Millenium Park
When: September 1st week

2. African Festival of the Arts

Immerse yourself in the African culture and heritage with the African Festival of Arts. This festival is a 4-day admission-free annual event that features African music, art, dance, history, and much more. More than 300 African artisans and vendors organize a display of artifacts, textiles, crafts, and art. If you are an artist or an art-lover, spend your September in Chicago immersed in artwork combined with great food because it is the best way to go. 
Address: 6200 S Drexel Ave, Chicago, IL 60637
When: 1st week of September

3. North Coast Music Festival

The North Coast Music Festival is an annual event held in Huntington Bank Pavilion on Northerly Island. The festival features EDM, hip hop, rock acts, and several installation artists. The festival first started in the year 2010 and received positive reviews. Since then, the festival is organized every year during the fall. Disclosed several weeks before the festival is the lineup that includes artists like Major Lazer, SG Lewis, Cashmere Cat, Bif Wild, etc.,
Location: Huntington Bank Pavilion on Northerly Island
When: Labour Day Weekend
Buy tickets at:

4. Riot Fest

Rock, Punk, Hip-Hop, and alternate Rock are the specialties of the Rio Fest. The Rio fest is a 3-day annual fest that started in the year 2005. It has since become an outdoor fest expanding to Toronto and Denver as well. While being amply mesmerized by the music, visitors can also enjoy rides, games, and food from different vendors. The lineup includes several artists, which are revealed weeks before the fest on their website.
When: September 2nd week 
Where: Douglass Park
Book Tickets at:

5. Oktoberfest

Get ready to celebrate Chicago German-style with the Octoberfest. Experience the beer festival with Oktoberfest Chicago Cruise, or dive-into into the pith of Oktoberfest with beer, live german-band music, food by Paulina Market, and more. This three-day annual fest will leave the visitors with a thoroughgoing unforgettable experience!  
Where: St. Alphonsus Church
When: September 3rd week, dates may vary.

6. Ravenswood Artwalk 

Over 10,000 tourists enjoy the Ravenswood Artwalk every year as they traverse through a weekend of food, arts, and music. Started by Judith Roth- estimable art advocate, the first Ravenswood Artwalk was in the year 2005. Over the next few years this tour of the arts and industry expanded at no-bounds and is now officially an extension of the Greater Ravenswood Chamber of Commerce.
Where: Deagan Building
When: September 14-15

7. Andersonville Arts Week  

Andersonville Arts Fest is hosted by the Andersonville Chamber of Commerce and produced by Amdur Productions. Andersonville arts week is an augment of Ansersonville's artwork plus fest with the fest that spans between Winona and Argyle street. It features over 50 local businesses and 100 artists with a display of numerous genres of art. 
When: September 19-22

8. Chicago Horror Film Fest

If you are a fan of the horror genre like me, get ready to embark on a spooky adventure with Chicago Horror Film Fest. It is an independent film festival that promotes horror films, both short and feature-length films from several media houses. All-in-all, the festival leaves no stone unturned to elicit the talented works of people from the industry.
When: 2nd week of September

9. Great Food Expo, Chicago


If you want to share your love for food and cooking, do not miss out on the Great Food Expo, as it is a paragon of culinary arts. With a perfect blend of entertainment, cooking secrets, kitchen decor, and more, the event welcomes cooking-enthusiasts of all ages and skill levels. Visitors can sample, sip and shop some of the best foods and beverages here. Unravel the cooking secrets of the Celebrity Chefs, elevate your home decor, or bring home the tasty products the Great Food Expo, will irrefutably crystallize as the highest point of your trip to Chicago!
Address: Donald E. Stephens Convention Center, 5555 N. River RoadRosemont`, IL 60018
When: 2nd week of September

10. Polonia Festival

The Polonia Festival is the largest Polish 4-day annual fall fest in the USA. With days of live music, good food, games, and entertainment, checks-off the Polonia Festival as a must-visit festival during your trip to Chicago in September!
When: 1st week of September
Where: Copernicus Center
Buy Tickets at:

11.West Town Art Walk  

Experience the artworks of residents and local businesses as they take over the neighborhood shops during the West Town Art Walk. The festival celebrates all kinds of art, which include music, culinary, visual, fashion, etc.,
When: September 27 to 28

12. Festival de la Villita  

Commemorate Mexico's independence in the Little Village neighborhood of Chicago. This three-day-long fest features Mexican food, dance, music, topped-up with the Mexican Independence Parade!
When: September 6 to 8 

13. ChicaGO Gourmet

The Chicago Gourmet fest features an amalgamation of local restaurants and cuisines commemorating the city's diverse cuisine. Moreover, the fest also hosts a Hamburger hop to kick-off the September month. It allows tourists to sink their teeth deep into their favorite burgers at over 100 restaurants across the city.
When: Third week of September
Buy Tickets at

14. Dessert Fest at the Lincoln Park Zoo

As the Lincoln Park Zoo is open all-year-round, therefore, to benefit the zoo, it hosts the Dessert Fest every September. The fest features dessert tastings from some of Chicago's famous locations with live entertainment, games, giveaways, and more! 
Where: Lincoln Park Zoo
When: 2nd week od September

6 FAQs on Chicago in September:

1. What to Pack?

As the weather is fickle in Chicago, always carry summer as well as winter clothes with you. We are not asking you to cover in layers, but to pack up a sweater or two causes no harm. As Chicago in September also experiences rainfall and sometimes storms, don't forget to carry an umbrella and a raincoat.

2. Where Should You Book Your Accommodation?

Hotel prices decrease as it is the end of the tourism month in Chicago. Hence, there is a good chance that tourists can book their accommodation at their favorite hotels at affordable prices.

3. What Are the Flight Rates?

Flight rates preempt high hotel rates as many people travel to Chicago in September for work. There might also be flight delays sometimes due to the storm, but the Chicago Airport is quite accommodable.

4. Is September as Fun as the Rest of the Months in Chicago?

Yes, Chicago in September is no less than the rest of the months. From the drive-in movies to the evening at the outdoor patios, Chicago has something for its tourists every month.

5. Are Chicago Passes worth It?

Chicago city pass and Go Chicago card are a few options to explore Chicago on a budget and not squander your money away. It is especially paramount during the tourist months in Chicago. But any time of the year carrying a Chicago Pass works in your favor. Tourists are allowed to visit the main attractions in Chicago with an entry fee. Therefore, these passes will help you skip-the-line and save up to 50 percent and more!

6. What Souvenirs Should You Carry?

Lastly, do not forget to enjoy your trip to Chicago in September and bring back your friends and family some souvenirs. While the Chicago skyline snow globe, Blue's CD, sport's jerseys are all too banal as souvenirs, there are certainly other options. Do not forget the Chicago seasonings, Pork Chocolates, old town oils, and last but not least, a bottle of White Blossom Mead and Half Acre Beer.

Chicago in September is a cornucopia of festivities. Varied events decorate the Windy City in September, welcoming artists, musicians from all over the world to indulge in art walks, culinary feasts, live music, beer fests, and more. Do not miss out on these cardinal events for a fun and unforgettable experience while in Chicago during the fall!

This post was published by Akshita Dhiman

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