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.
- $77-$81 — Atlanta
- $77-$87 — Boston
- $77-$87 — Dallas
- $81 — Houston (Sept.-Dec.)
- $87 — Baltimore
- $87-$127 — Los Angeles (Sept.-Dec.)
- $87-$127 — New York City
- $107-$127 — Denver
- $117-$147 — Miami (Sept. only)
- $127 — San Francisco (Sept. only)
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
- $97 — Boston to New York City (Dec.-April)
- $117 — Detroit to Orlando
- $127 — Washington, D.C., to Fort Lauderdale
- $137 — Houston to Miami (through Nov.)
- $267 — San Francisco to Fort Lauderdale (through Dec. 12)
- $277 — Los Angeles to New York City
- $279 — Seattle to New York City (Oct.-Nov.)
Cheap International Flights
- $330-$333 — Denver to San Juan, Puerto Rico (Sept.-Jan.)
- $388 — Denver to Charlotte Amalie, St. Thomas (Sept.-Jan.)
- $564 — New York City to Tokyo, Japan
- $593 — New York City to Phuket, Thailand
- $594 — Chicago to Dubai, U.A.E. (Sept.-Oct.)
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.
Fly.com Updates
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- Fare Calendars – This tool shows the best deals from the nearest major airport and allows users to create a custom fare calendar for any route (scroll to the bottom for this functionality).
Featured Image: Chicago Skyline from North Avenue Beach (Shutterstock.com)