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Chicago’s September Calendar of Events

September is one of the best times of year to be in Chicago. The weather is warm and the event calendar is full.

Things to Do in Chicago in September:

Chicago Jazz Festival

When: September 1-4, 2022
Neighborhood: The Loop
Address: Millenium Park
Cost: Free

An all-ages music festival featuring jazz legends and up-and-coming performers.

ARC Music Festival

When: September 2-4, 2022
Neighborhood: West Loop
Address: Union Park
Cost: $279 for a 3-day pass

A house and techno festival with a lineup that includes Fatboy Slim, Mike Dunn, DJ Tennis, and Kasablanca.

Great American Lobster Fest

When: September 2-4, 2022
Neighborhood: Streeterville
Address: Navy Pier

The Midwest’s largest lobster and seafood festival has live music, family-friendly activities, an artisan market, plus food and drinks.

Taste of Polonia

When: September 2-5, 2022
Neighborhood: Jefferson Park
Address: The Copernicus Center

Taste of Polonia is a family-friendly event with four stages, over 35 bands, kids activities and play areas, carnival rides and games, a beer garden, and food vendors.

West Loop Art Fest

When: September 3-4, 2022
Neighborhood: West Loop
Address: Fulton and Peoria

Shop art representing diverse mediums at a wide range of price points at this festival.

Sundays on State

When: September 4, 2022, 11 am – 6 pm
Neighborhood: The Loop
Address: State Street Between Lake and Monroe
Cost: Free

An interactive block party with shopping, outdoor dining, art, entertainment, and recreation.

Bike the Drive

When: September 4, 2022
Neighborhood: Lakefront neighborhoods
Address: DuSable Lake Shore Drive

On the morning of Bike the Drive, all lanes of traffic, in both directions, on DuSable Lake Shore Drive are closed so that cyclists can bike a 30-mile course. The event does require prior registration and tickets. Bike rentals are available.

Samosa Stroll

When: September 8, 2022
Neighborhood: Rogers Park
Address: Devon Avenue between Damen and Kedzie

A one night food event in Chicago’s Little India neighborhood.

Renegade Craft Fair

When: September 10-11, 2022
Neighborhood: West Town/Wicker Park
Address: Division between Paulina and Damen

A massive market featuring art, crafts, clothing, and artisan goods that takes over Division Street along the border of West Town and Wicker Park.

River North Design District Fall Gallery Walk

When: September 9, 2022, 5 pm – 8 pm
Neighborhood: River North
Address: Starts at Altalia Furniture, 410 W Grand Ave.

An event that brings together fine art galleries and design showrooms. The event takes place across dozens of galleries and showrooms and top designers select their favorite artworks.

Chicago German American Oktoberfest

When: September 9-11, 2022
Neighborhood: Lincoln Square
Address: Lincoln and Western

A fest that includes live music, carnival games, performances from traditional dance groups, the Von Steuben Parade, and German food and beer.

Throwback Music Festival

When: September 9-11, 2022
Neighborhood: Gladstone Park
Address: Milwaukee between Elston and Peterson

A celebration of music from the ’50s, ’60s, and ’70s with food, an arts and crafts market, a vintage car display, a pet parade, and a Miss Throwback contest.

Edgewater Arts Festival

When: September 10-11, 2022
Neighborhood: Edgewater
Address: Granville between Broadway and Sheridan

An arts festival featuring arts working in the mediums of ceramics, glasswork, clothing and textiles, jewelry, painting, photography, and mixed media. In addition to art, the fest has live music including performances from the Andersonville School of Rock.

Celestial Ball

When: September 10, 2022
Neighborhood: Museum Campus
Address: Alder Planetarium

The Adler Planetarium’s largest annual fundraising event.

Moon Festival / Mid-Autumn Festival

When: September 10-12, 2022
Neighborhood: Chinatown
Address: Ping Tom Memorial Park

The Moon Festival (also called the Mid-Autumn Festival) takes place on the 15th of the 8th lunar month and falls sometime between mid-September to early October. This is the time of harvest and when the moon is believed to be its fullest and brightest. The event takes place at Ping Tom Memorial Park and traditional Chinese folk dancing, storytelling, lantern making, music, moon cakes, and a lantern parade.

Lakeview East Festival of the Arts

When: September 10-11, 2022
Neighborhood: Lakeview
Address: Broadway between Belmont and Hawthorn

A juried art fair featuring works from over 150 artists in the mediums of painting, sculpture, photography, furniture, jewelry, and more. This event is an art sale, with live music, and family-friendly activities.

Printers Row Lit Fest

When: September 10-11, 2022
Neighborhood: South Loop
Address: South Dearborn Street

This is the largest free outdoor literary showcase in the Midwest. During the event, hundreds of booksellers sell antique, new, and used books. The Printer’s Row Lit Fest is an opportunity to support independent bookstores and to hear talks from authors and journalists.

Ravenswood ArtWalk

When: September 10-11, 2022
Neighborhood: Ravenswood
Address: Ravenswood and Lincoln Square

A weekend-long celebration of Ravenswood’s artists and creative community that includes open studios and galleries, dance performances, and an outdoor arts market featuring over 50 local artists.

Chicago House Music Festival

When: September 16, 2022
Neighborhood: The Loop
Address: Millennium Park
Cost: Free

House music originated in Chicago and this festival features live performances and DJs.

Riot Fest

When: September 16-18, 2022
Neighborhood: North Lawndale
Address: Douglass Park
Cost: $100 and up

A three-day rock music festival with five stages and over 80 bands. The lineup includes My Chemical Romance, Nine Inch Nails, Yellowcard, Yeah Yeah Yeahs, Ice Cube, Jimmy Eat World, and Alkaline Trio.

Lakeview Taco Fest

When: September 17-18, 2022
Neighborhood: Lakeview
Address: Southport between Addison and Roscoe

Sponsored by Sam Adams, Lakeview Taco Fest takes place in September and involves local restaurants competing for the title of “Best Taco”.

Andersonville Vintage Market

When: September 21, 2022, 10 am – 3 pm
Neighborhood: Andersonville
Address: Catalpa Street between Ashland and Clark

During the Andersonville Vintage Market the neighborhood’s vintage and antique stores take over a stretch of Catalpa Street between Ashland and Clark.


When: September 22, 2022
Neighborhood: The Loop offers the best viewpoints
Address: Any East-West Street

Chicagohedge is an event when the sunrise and sunset happen to align with the skyline. It happens twice a year, usually around the spring and fall equinoxes. This event the perfect way to say farewell to summer and hello to fall.

Chicago Gourmet

When: September 22-25, 2022
Neighborhood: The Loop
Address: Millennium Park

A weekend-long event showcasing some of Chicago’s best restaurants. Guests can try bites from dozens of restaurants, taste wines, and watch cooking demonstrations from well-known chefs. Purchase tickets in advance since events do tend to sell out.

Hyde Park Jazz Festival

When: September 24-25 2022
Neighborhood: Hyde Park
Address: Midway Plaisance Park
Cost: $10 suggestion

An event dedicated to supporting jazz music. The 2022 has not been announced yet but the 2021 event showcased over two dozen bands.

West Town Art Walk

When: September 23-24, 2022
Neighborhood: West Town
Address: throughout West Town

An event hosted by West Town galleries, home stores, and garden shops that celebrates local art with walking tours and special events.

Buen Provecho! Taste of Pilsen

When: To Be Announced
Neighborhood: Pilsen
Address: Plaza Tenochtitlan

An event held in conjunction with Mexican Independence Day that invites participants to taste bites from over 20 neighborhood restaurants, cafes, and bakeries. This event is different from other Chicago neighborhood food events because participants walk from restaurant to restaurant, instead of having the restaurants set up booths at a central location. 

Revolution Brewing Oktoberfest

When: September 24-25, 2022
Neighborhood: Logan Square
Address: 2323 North Milwaukee Ave

This beer-centric street festival features live music and Revolution Brewery’s seasonal Oktoberfest beer. In the past, metal bands played on Friday.