10+ Things to Do in Chicago in the Fall
There’s nothing like autumn in the Windy City.

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Architecture River Cruise - If you love the outdoors and can’t get enough of the cooler weather, then a boat cruise or tour is a smart idea. Try one now before the weather gets too cold!
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Art Institute of Chicago - Spend an afternoon at the Art Institute of Chicago, voted the #1 Museum in the World in TripAdvisor’s 2014 Traveler’s Choice Awards.
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Chicago’s Museum Campus - Take the kids to explore Chicago’s family-friendly Museum Campus, comprised of the perennially popular Shedd Aquarium, The Field Museum, and Adler Planetarium.
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SkyDeck Chicago - Formerly known as Sears Tower, the Willis Tower is the home of the famous Chicago SkyDeck Observatory.
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Go for a Relaxing Bike Ride - Enjoy the great outdoors before the chill of winter sets in. Chicago in the fall is perfect for invigorating walks, bike rides, and getting out on Lake Michigan.
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Chicago Botanic Garden Events - The beautiful garden is host to lots of fun events this fall season.
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Bacon and Beer Classic, Daley Plaza - This event is one for the bacon lovers — which, honestly, probably includes a lot of us.
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Great Highwood Pumpkin Festival, Highwood, IL - Check out The Great Highwood Pumpkin Festival, where they will attempt to break the Guinness World Records for the most pumpkins carved in one place.
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EXPO CHICAGO, Navy Pier - Chicago’s iconic Navy Pier, known as the lakefront playground, will play host to EXPO CHICAGO, the International Exposition of Contemporary and Modern Art.
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Apple Picking - You don’t have to go far outside of the city to suddenly find yourself on a farm or orchard. Just head an hour outside of the city and you’ll find lots of apple orchards, etc.
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Go to a Street Festival - Street festivals are the best festivals. Check out one of the many happening in September for a round-up of the ones you can’t miss!
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Take in a Cubs or White Sox game — their seasons are winding down this time of year and you never know who will be in the post-season!
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The NFL season has also just started, so if you’re a Chicago Bears fan, head to Soldier Field.
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Cheer on the runners (or log some miles yourself!) in the Chicago Marathon, held each year in October.
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Keep an eye on the concert schedule for the fall. Chicago attracts some pretty huge names so you’ve got a good chance of seeing your favs.
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The theatre scene in Chicago is practically unrivalled. Sign up for Gold Star to get discounted tickets on local shows.
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