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.
See the Tony Award-winning "A Gentleman's Guide to Love & Murder" at the Bank of America Theatre from September 29 through October 11.
Attend Chicago’s inaugural Museum Week from October 1 to 7. Twelve museums, including the Adler Planetarium and Chicago History Museum, are participating.
Chicago proves New York isn't the only Fashion Week hub from October 4 to 12.
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.
The Whiskey Extravaganza on October 8 is the perfect excuse to dress up and taste an unlimited amount of whiskeys from around the globe.
Catch an indie film at the Chicago International Film Festival, running October 15 to 29.
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.
Drink like a German and enjoy traditional folk music at one of the city's many Oktoberfest celebrations.
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.
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.”
Sample domestic and international seasonal beers at the Chicago Beer Festival on October 24 at Union Station.
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.
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.
Rent a Divvy bike for $9.95 and ride along Lake Michigan on the 18-mile 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.
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.
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.
Check out one of the pop-up pumpkin patches or Halloween events in parks around Chicago throughout October, hosted by the Chicago Park District.
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.
Football and fall are synonymous. Watch a Bears game at Soldier Field, or venture to a sports bar.
See the 2015 Stanley Cup winners in action at a Blackhawks game.
And for those who prefer basketball over ice hockey, go to a Chicago Bulls game.
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.
Find a grassy spot on Millennium Park's Great Lawn and sprawl out for an afternoon picnic.
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.
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.