Have a group visiting Chicago during the fall? There's no shortage of fun things to do, especially with this packed lineup of large-scale festivals and special events in Chicago on the calendar. From cultural celebrations to fine art productions to music festivals and special anniversary seasons, this is the hit list.


Chicago Gourmet

Chicago Jazz Festival
September 1 - 4, 2016
Millennium Park

As the largest free festival of its kind in the world, expect hundreds of thousands of attendees flocking to Millennium Park to watch top name jazz performers as they take the stage in Jay Pritzker Pavilion.

Chicago German-American Fest
September 9 - 11, 2016 
N. Western Ave. and N. Lincoln Ave.

This annual event celebrates all things German. Traditional interactive cultural programs, music, dancing, and of course great food and beverages are available at this three-day festival in the Lincoln Square neighborhood.

18th Annual World Music Festival Chicago

September 9 - 25, 2016 
Multiple Locations

Showcasing international musicians at venues throughout the city, the 18th Annual World Music Festival Chicago celebrates diverse music from around the world with free musical performances at Jay Pritzker Pavilion and an array of cultural performances, such as contemporary Moroccan music in the Gnawa tradition and Southern Slavic folk played by a tamburitza band.

3rd Annual Fifth Star Awards

September 14, 2016 
Jay Pritzker Pavilion

This free public celebration in the heart of Millennium Park honors outstanding Chicago artists and arts institutions with a lineup of tribute videos and captivating live performances.

September 22 - 25, 2016 
Navy Pier

Navy Pier's Festival Hall will be bursting with creative energy, as 140 prominent international galleries from 16 countries and 45 cities will present thought-provoking artwork, while expert panels, a lecture series, site-specific installations and a selection of forward-thinking film, video and new media works will give attendees plenty to see, do and think about during this four-day event.

Reeling: The 34th Chicago LGBTQ+ International Film Festival

September 22 - 29, 2016 
Landmark Century Centre Cinema

As the second longest-running LGBTQ film festival in the world, Reeling has established itself as a groundbreaking event, featuring diverse films and invaluable events. This year's festival will screen approximately 100 independent films, as well as special events, industry panels and seminars.

Oktoberfest Chicago
September 23 - 25, 2016
John C. Kluczynski Federal Plaza

Get ready to toast to the 30th anniversary of this free annual event — Chicago's largest and longest-running Oktoberfest party — which includes festivities such as a tapping of the keg, live music, dancing and classic German dishes such as bratwurst and Bavarian soft pretzels. 

Chicago Gourmet

September 23 - 25, 2016 
Millennium Park

Eat, drink and be merry at the nation's leading culinary experience, where chefs, master sommeliers, and wine, spirit, and beer-makers show off their skills and wares in a series of live cooking demonstrations, interactive wine and cocktail seminars, and — of course — plenty of tastings. Expect a star-studded lineup of celebrity chefs, including the likes of Jose Garces, Stephanie Izard and Richard Sandoval.



Open House Chicago

Chicago Architecture Biennial

Dates TBA
Multiple Locations

Over 100 participating architects and artists based in more than 25 countries will converge for this free event showcasing exhibitions, large-scale installations and programs throughout the city.

Historic Pullman House Tour
October 8 - 9, 2016 
Pullman Neighborhood

For one weekend, residents in the historic Pullman neighborhood open their doors to the public for this annual tour, where attendees can peek beyond the beautiful facades to see inside grand mansions, workers' cottages and unique apartment buildings.

Chicago International Film Festival
October 13 - 27, 2016 
AMC River East 21

A must for movie lovers, this annual festival screens more than 150 works from more than 60 countries, from narrative features and documentaries to short films.  

Open House Chicago
October 15 - 16, 2016 
Various Locations

For 48 hours, go behind-the-scenes of 150 buildings across Chicago — from hidden gems to architectural icons — in this free public festival by Chicago Architecture Foundation.

Chicago Ideas Week

October 17 - 23, 2016 
Multiple Locations

Get inspired at this empowering experience, where entertaining and accessible events, grassroots initiatives and fascinating content presented by innovative speakers (think: A-list actors, eminent entrepreneurs, tech moguls and politicians) move attendees to action. Many events cost only $15 per ticket, making it an affordable and accessible experience for community members.

The Halloween Gathering

October 22, 2016 
Balbo Street to Monroe Street
Harnessing the imagination of Chicago's creative community, artists from world-renowned institutions like the Field Museum, The Art Institute of Chicago and Chicago Symphony Orchestra will combine forces to produce an over-the-top Halloween parade featuring large-scale creations, costumed performers, music and dance as it moves north from Balbo to Monroe in a spectacular procession.

November 3 - 6, 2016 
Navy Pier
View sculptural objects, functional art and design at this annual gallery-presented art fair, where approximately 35,000 attendees peruse the wares of 80 dealers. This artistic gathering also offers a lecture series and special events examining the artwork on display.


Related Listings

Navy Pier
600 E. Grand Ave.
Chicago, IL 60611
(312) 595-5300

Steppenwolf Theatre Company
1650 N. Halsted St.
Chicago, IL 60614
(312) 335-1650

The Joffrey Ballet
Joffrey Tower, 10 E. Randolph St.
Chicago, IL 60601
(312) 739-0120

Lyric Opera of Chicago
20 N. Wacker Dr., Ste. 860
Chicago, IL 60606
(312) 827-5600

Featured Partners