Head on over to the Windy City this fall, which is probably the best season to be in Chicago. That’s when the summer crowds have dispersed, the weather’s cooled down making exploring the city a breeze and flight and hotel deals start popping up. And if you’re in the mood for leaf-peeping, you don’t have to travel too far from downtown, as places such as the Lincoln Park North Pond Sanctuary just north of the city, or you can even head outside the city to the Chicago Botanic Garden with their ever changing landscape of foliage based on the season.

And with flights the deal experts at Fly.com have found, now’s a great time to start planning your fall getaway.

If the Midwest is not for you, we have also found some hot deals to Florida, New York City, Asia & more!

Cheap Flights to Chicago

The prices below represent a savings of up to $125 on typical roundtrip prices. These fares are not part of an airline sale and may disappear at any time, so book ASAP.

Availability varies by route. Click on the Fare Calendar links below to find the best dates to travel September to November, unless otherwise noted (blackouts may apply). All prices roundtrip, including taxes.

More Cheap Flights

Chicago’s deep dish pizza not doing your waistline any favors? We have more great deals to Florida, New York City, Asia & more!

The prices below represent a savings of up to $350 on typical roundtrip prices. These fares are not part of an airline sale and may disappear at any time, so book ASAP.

Availability varies by route. Click on the Fare Calendar links below to find the best dates to travel September to December, unless otherwise noted (blackouts may apply). All prices roundtrip, including taxes.

Cheap Domestic Flights

Cheap International Flights

Don’t see fares from your hometown? Browse Today’s Best Fares from your city. And for hotel suggestions, check out Fly.com/hotels for deals and offers.

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Featured Image: Chicago Skyline from North Avenue Beach (Shutterstock.com)

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Kim has been hunting flight deals and writing travel articles for over 13 years. His articles have appeared in the Boston Herald, Chicago Daily Herald, and Frommer’s Budget Travel, among other publications. Amsterdam, Bangkok, Rome, and Sydney are some of his favorite destinations and he aspires to one day live in Italy. La dolce vita!

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