27 awesome things to do in Chicago this fall

caption
Nothing beats the quiet of daybreak at The Cloud Gate (aka “the bean”) in Millennium Park
source
Flickr/Mike Warot

Ah, Chicago in the fall. That fleeting moment before the temperature drops below zero and snow blankets the city.

Whether you’re a resident or are just passing through on business, it’d be a shame to let the fair season fly by without a bike ride along Michigan Lake or a visit to one of the city’s pop-up pumpkin patches, not to mention a slew of cultural events, beer festivals, and more taking place just about every weekend.

Keep scrolling for the 27 best ways to soak up fall in the Windy City.


Watch performers from all over the world at UniverSoul Circus in Washington Park from September 22 through October 18.

source
Facebook/UniverSoul Circus

Click here to purchase tickets and learn more »


See the Tony Award-winning “A Gentleman’s Guide to Love & Murder” at the Bank of America Theatre from September 29 through October 11.

source
Facebook/A Gentleman’s Guide to Love and Murder

Click here for dates and show times »


Attend Chicago’s inaugural Museum Week from October 1 to 7. Twelve museums, including the Adler Planetarium and Chicago History Museum, are participating.

source
Wikimedia Commons

Click here for the list of participating museums »


Chicago proves New York isn’t the only Fashion Week hub from October 4 to 12.

source
Flickr/mainstream

Click here to learn more about Chicago’s fashion week »


Outdoor music festivals may have ended, but indoor concerts are in full swing. Check out performers like Ariana Grande on October 2, The Who on October 15, and Stevie Wonder on October 16.

source
Brad Barket/Getty Images

Click here for Time Out Chicago’s must-see fall concert list »


The Whiskey Extravaganza on October 8 is the perfect excuse to dress up and taste an unlimited amount of whiskeys from around the globe.

source
Flickr/Dominick

Click here to purchase tickets »


Catch an indie film at the Chicago International Film Festival, running October 15 to 29.

source
Facebook/Chicago International Film Festival

Click here for a sneak peek at this year’s festival »


If you enjoy bacon and beer, you’ll love the Bacon and Beer Classic on October 10. It’s a day full of craft brews and bacon-inspired bites from local restaurants at Soldier Field.

source
Facebook/Bacon and Beer

Click here to purchase tickets or learn more »


Drink like a German and enjoy traditional folk music at one of the city’s many Oktoberfest celebrations.

source
Flickr/46137

Click here for a list of Oktoberfest events »


Stop by McCormick Place for the Abbott Health & Fitness Expo — featuring over 200 exhibitors on October 9 and 10 — leading up to the Chicago marathon on October 11.

source
Flickr/josiahmackenzie

Click here to learn more about the expo »


Head to Harris Theater on October 23 or 24 to see the world-renowned Giordano Dance Chicago. Says the Chicago Tribune: “The mood is pure joy, the energy unstoppable.”

source
Facebook/Giordano Dance Chicago

Click here to read the Chicago Tribune article »

Click here to purchase tickets »


Sample domestic and international seasonal beers at the Chicago Beer Festival on October 24 at Union Station.

source
Facebook/Chicago Beer Festival

Click here to purchase tickets and learn more »


Burn off all the Halloween candy you’ve been eating during the Trick or Treat Trot 6k on October 25 in Evanston. Costumes are welcome at this family-friendly event.

source
Facebook/Trick or Treat Trot

Click here to learn more about the Trick or Treat Trot »


Try 250 different types of wine from around the world in four hours during Wine Riot on October 16 to 17 in the Great Hall at Union Station.

source
Facebook/Second Glass

Click here to purchase tickets and learn more »


Rent a Divvy bike for $9.95 and ride along Lake Michigan on the 18-mile Lakefront Trail.

source
Facebook/Divvy Bikes

Click here to learn more about Divvy »

Click here to learn more about the Lakefront Trail »


Over 20 entrants from around Chicago will compete in the 7th Annual Charitable Chili Cook-Off on November 7, hosted by Arts of Life. Chilis are separated into two categories: vegetarian-friendly and meat lovers.

source
Vanessa Escobeda Barba

Click here to learn more about the chili cook-off »


Take a day-trip and go apple picking at one of the surrounding orchards, many of which offer fresh baked goods and warm apple cider.

source
Flickr/jenniferboyer

Click here for a list of local orchards and farms »


Savor a long Sunday brunch at Cindy’s, located in the trendy Chicago Athletic Association Hotel. The rooftop boasts beautiful panoramic views of the city.

source
Facebook/Chicago Athletic Association Hotel

Click here to learn more about Cindy’s »


Check out one of the pop-up pumpkin patches or Halloween events in parks around Chicago throughout October, hosted by the Chicago Park District.

source
Flickr/lizwest

Click here to see the schedule »


Test out Hyde Park’s newest dumpling spot, PACKED, opening at the end of September. Chef Michael Sheerin elevates the humble morsel with ingredients like king crab and brown butter wrappers.

source
Facebook/PACKED: dumplings reimagined

Click here to learn more about Chicago’s newest dumplings restaurant »


Football and fall are synonymous. Watch a Bears game at Soldier Field, or venture to a sports bar.

source
Wesley Hitt/Getty Images

Click here to see this year’s schedule »


See the 2015 Stanley Cup winners in action at a Blackhawks game.

source
Facebook/Chicago Blackhawks

Click here to see this year’s schedule »


And for those who prefer basketball over ice hockey, go to a Chicago Bulls game.

source
Jonathan Daniel/Getty Images

Click here to see this year’s schedule »


No Shave November just got fancy. On November 13, attend the Mustachio Ball for a formal night of live performances, gourmet food and cocktails, costumed dancers, and more.

source
Flickr/garryknight

Click here to learn more about the Mustachio Ball »


Find a grassy spot on Millennium Park’s Great Lawn and sprawl out for an afternoon picnic.

source
Flickr/lasequencia

Click here for a list of things to see and do at Millennium Park »


Indulge in a night of Shakespearean magic with “The Tempest,” adapted and directed by Aaron Posner and Teller. Catch the show at the Chicago Shakespeare Theater through November 8.

source
Facebook/Chicago Shakespeare Theater

Click here for tickets and show times »


Celebrate the city’s architectural innovations at the first-ever Chicago Architecture Biennial. The multi-platform event runs from October 3 to January 3, 2016.

source
Flickr/allenmcgregor

Click here to learn more about the Chicago Architecture Biennial »