This week, our experts found some incredible deals to Chicago. We recommend visiting towards the beginning of the travel window, as we are not sure whether the Cubs or White Sox will make it to October. Sorry Chicago fans! Only kidding! There are plenty of other places to explore to keep travelers of all ages entertained, like Navy Pier or the Magnificent Mile.
Cheap Flights to Chicago
The prices below represent a savings of up to $150 off 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 from August to November, unless otherwise noted (all prices roundtrip, including taxes):
- $78-$98 — Cleveland to Chicago (Oct.-Nov.)
- $98-$118 — Washington, D.C. to Chicago (Sept.-Nov.)
- $138-$178 — Denver to Chicago
- $148-$158 — Dallas to Chicago
- $198 — Orlando to Chicago
- $188-$198 — New York City to Chicago
- $238-$258 — San Francisco to Chicago
- More cheap flights to Chicago
More Cheap Flights
If Chicago isn’t for you, here is a selection of our favorite fares to destinations in the U.S. and around the world.
Availability varies by route. Click on the Fare Calendar links below to find the best dates to travel from August to November, unless otherwise noted (all prices roundtrip, including taxes):
- $97 — Charlotte to Washington, D.C.
- $128-$158 — Kansas City to Las Vegas
- $176-$196 — New Orleans to New York City (Sept.-Dec.)
- $458 — Portland to Honolulu
- $629-$655 — New York City to Milan, Italy (Sept.-Dec.)
Note: Most of the deals above are available in the opposite direction as well, so be sure to search.
For hotel suggestions, deals or offers, check out Fly.com/hotels.
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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 (Shutterstock.com)
