Fall Events in Chicago

Summer may be the best time in Chicago, but the season of fall is a close second. This time of year marks a lot of annual cultural and architectural events that really define the city around them. Knowing that, here are the best fall events in Chicago.

Historic Pullman House Tour

October 8 – 9, 2016
Pullman Neighborhood

The fall season is certainly a great time for marvelling in Chicago’s amazing architecture and history (make sure to check out Open House Chicago later on in this list if that’s your thing). The Historic Pullman House Tour takes place in (where else) Pullman and members of the public invite people into their gorgeous mansions to see how the other half lives.

Rocktober Beerfest
October 7 – 9, 2016

Enjoy the great outdoors before the bitter winter sinks in! Rocktober Beerfest takes place under a heated tent at Randolph and Ogden. You’ll enjoy the opportunity to indulge in beer and bratwurst while enjoying local live music.

Chicago International Film Festival

October 13 – 27, 2016
AMC River East 21

Chicago’s International Film Festival is a series of screenings not to be missed by the true film buff. This annual festival features films from over 60 countries, for a total of more than 150 movies to choose from. Regardless of what you’re into, there’s something for everyone – features, documentaries, short films, and more!

Open House Chicago

October 15 – 16, 2016
Various Locations

Architecture buff? Or just like feeling like a VIP? At Open House Chicago, you get behind-the-scenes access to 150 historical buildings across Chicago. But you’ll have to act fast – this event only happens once a year for 48 hours. If you miss it, you potentially miss access to these hidden gems and architectural icons until Open House Chicago next year!

Chicago Ideas Week


October 17 – 23, 2016
Various Locations

A number of events that go on for a week mid-October, featuring people of interest and thought leaders across multiple industries (A-list actors, entrepreneurs, tech moguls, and politicians). Events range from talks to hands-on “labs” and are extremely accessible, starting at just $15/ticket.

The Halloween Gathering


October 22, 2016
Balbo Street to Monroe Street

Artists from the local creative community and beloved institutions (The Field Museum, Art Institute, and more) put together a Halloween parade to put all others to shame. You can expect music, dance, costumed performers, and detailed creations from the minds of these creatives.

With so much to do, good luck choosing from the best fall events in Chicago. Is there something we missed? We’d love to hear about the events you’re attending! Let us know where you’ll be in the comments.

Author: Maddy Osman, an SEO Content Strategist who has a passion for blogging. Her lifestyle blog, ChicagoCheapAss, shows young adults how to find the best deals and values in Chicago!