The Ultimate Chicago Fall Festival Guide  image


The Ultimate Chicago Fall Festival Guide

Because the "we-have-all-four-seasons" Midwestern superiority complex is real.

Summer may be over, but we still have a few months before it’s dark at 4pm and we can’t be outside without 29 layers of clothes. And because Chicagoans will take every opportunity to enjoy the time we have left before being plunged into wintery darkness, street festivals are still a thing. From Halloween parades, to food fests, to open houses in some of the city’s most historic buildings, here’s our guide to the Best Fall Festivals In Chicago.

This is a running list so check back in for the latest details. For more autumn-related stuff, check out this list of fall things to do and eat around the city, and our fall road trip guide.


October 2022

The Ultimate Chicago Fall Festival Guide  image

Lincoln Square Apple Fest

Lincoln Square, October 1-2

Pumpkins may get a lot of the spotlight during the fall, but Lincoln Square’s Apple Fest is back to remind us that it’s also the season for your doctors’ favorite fruit. It’s the iconic festival’s 35th year, and in addition to plenty of apple-based food and drinks, there will be local produce and merchandise for sale, and live music.


Old Town, October 1-2

WingOut is a chicken wing festival taking place in the parking lot of St. Michael’s Church. In addition to food from restaurants like Jake Melnick’s, Woodie’s, and El Campéon, there will be live music and you can vote for The Best Kick, Most Original, or Best Overall. Both general admission and VIP tickets with an AYCE option can be purchased here.

Publican Oktoberfest 

Fulton Market, October 2nd

On October 2nd, The Publican is serving a prix fixe meal in honor of Oktoberfest. The dinner is $120 per person and will have dishes like beer cheese pretzels, smoked whitefish dip, pork schnitzel, and German apple cake. Reservations can be made here.

Chicago Beer Fest 

Field Museum, October 8

Ben Stiller won’t be making a cameo and taxidermied animals won’t be coming to life, but you can spend a night at The Field Museum during The Chicago Beer Festival on October 8. From 7pm-11pm you can sample 65 breweries’ seasonal beers and check out exhibits that will remain open during the festival. Click here for tickets.

Dovetail and Begyle Oktoberfest

Ravenswood, October 8-9

For the sixth year, Dovetail and Begyle breweries are hosting their annual Ravenswood street fest, Ocktoberfestiversary. They’ll have beer, live music, and food trucks from restaurants like Happy Lobster, Donermen, and The Fat Shallot.

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Time Out Market Oktoberfest

Fulton Market, October 7-9

Also in the second weekend of October, Time Out Market will be hosting its own Oktoberfest celebration. In addition to their usual line-up of restaurants, they’ll have kid-friendly events like storytime and face-painting, live polka, and a stein-hoisting competition.

Lincoln Park Wine Fest

Lincoln Park, October 7-9

For more booze-related fun, you can check out the Lincoln Park Wine Fest in Jonquil Park. In addition to the 27 different wine-makers that will be featured (some are only available if you have VIP admission), there will also be a few tents serving food. Registration can be found here.

Open House Chicago

Across Chicago, October 15-16

Open House Chicago is a citywide event organized by the Chicago Architecture Center that highlights some of Chicago’s most historic and culturally significant buildings. People will be able to get a special inside look into buildings across the city like the Willis Tower, The Cliff Dwellers Club, or Apollo’s 2000 Theater, and can follow self-guided tours using their app.

Music Box Theatre's Scared Stupid Movie Festival

Lakeview, October 1-31

For the entire month of October, The Music Box Theatre is hosting a horror movie series called Scared Stupid. Every night, they are showing a different movie, from old films like Nosferatu to newer cult classics like Jennifer’s Body. Get tickets and check out the full lineup here.

The Ultimate Chicago Fall Festival Guide  image

photo credit: James Richard IV

Upside Down Arts Parade 

Logan Square, October 22

The Upside Down Arts Parade is a “reverse” parade where visitors walk down a stretch of Washington Square Park and visit 20-25 performance stations with everything from acrobats to musical acts to puppet shows. People are encouraged to wear costumes, but either way, you’ll get a candy-filled goody bag just for showing up.

Arts In The Dark Parade

The Loop, October 29

The Arts in The Dark Parade is also hosted by the same team behind the Upside Down Arts Parade, but is an actual parade. You can expect floats and performances from Chicago institutions like the Looking Glass Theater Company, Joffrey Ballet, and local music groups.

Haunted Halsted Halloween Parade

Northalsted, October 31

Instead of spending Halloween trying to keep track of which of the 18 Top Gun pilots you’ve already talked to, you can check out Northalsted’s annual Halloween Parade. Expect typical parade stuff—floats and music, along with a costume contest with over $4000 in prizes.

November 2022

Thanksgiving Day Parade

The Loop, November 24

You know what this is. There will be giant balloons, lavishly decorated floats, and live musical performances—but if you’re on dinner duty (or don’t want to deal with crowds of strangers) you can always just watch the whole thing on TV.

Suggested Reading

17 Things To Do For Halloween In Chicago If You Haven’t Made Plans Because Life Is Scary Enough image

17 Things To Do For Halloween In Chicago If You Haven’t Made Plans Because Life Is Scary Enough

Make the most of the weekend with pop-ups, parties, bar crawls, and more.

Where To Do Fall Stuff Within 90 Minutes Of Chicago image

Because everyone likes pumpkins and fresh air.

The “F*ck It’s Almost Fall” Guide image

Where to go when you realize summer is slipping away and you’ve completely wasted it.

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