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):

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):

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.

Fly.com News and Updates

For the latest information:

Featured Image: Chicago Skyline (Shutterstock.com)

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Fly.com regularly posts guest contributions from travel experts around the world. These articles are written by journalists, bloggers, travel enthusiasts, and specialists from within various segments of the travel industry. Each has an undeniable passion for travel that enables them to share a unique and valuable point of view. We hope you enjoy their stories and advice!

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