Cheap flights from Key West, FL to Chicago, IL

Travelers frequently search for route combinations, such as Key West and London, Orlando, Hamilton, New Orleans, Nashville, Las Vegas, San Juan, Glasgow, Manchester, Denver, New York, Miami, Los Angeles, Atlanta, Mexico City, Bogotá, Dallas, Phoenix, Philadelphia, San Francisco.

Travelers frequently search for route combinations, such as Chicago and London, Dublin, Manchester, Toronto, Athens, Orlando, San Francisco, Hyderabad, New York, Las Vegas, Edinburgh, Denver, Bangkok, Minneapolis, Riga, Glasgow, Austin, San Juan, Edmonton, Tallinn.

The main airport in Key West is Key West International. It is also served by Miami International, Key West International.

The main airport in Chicago is O Hare International. It is also served by Gerald R. Ford International, General Mitchell International, Dane County Regional, South Bend International, Fort Wayne International, Quad City International, General Wayne A. Downing Peoria International, Central Illinois Regional, Muskegon County, University of Illinois Willard.

Yes, it's possible to combine different modes of transport between Key West and Chicago thanks to our Virtual Interlining technology. Making use of not only flights but also trains and buses between Key West and Chicago can give rise to new adventures. Read more about how Virtual Interlining works on Kiwi.com Stories.

Virtual Interlining provides a revolutionary way of traveling. You can combine different modes of transport like flights, trains, and buses into one itinerary. And this often saves money. Thanks to the world's largest carrier database, the Kiwi.com search function enables anyone to mix and match different modes of transport easily.

Currently, you can fly between Key West and Chicago with United Airlines.

If you don’t have specific dates for your trip between Key West and Chicago, you can enter a date range into the departure and return fields. Most carriers on the Kiwi.com website allow you to search and book up to six months from the day of your search. Order the search results by the best, cheapest, or fastest route, or find the cheapest outbound and return combination in the pricing table.

Traveling between Key West and Chicago, you can choose between direct (nonstop) flights or flights with one or more stops. You can select the number of stops on your journey, including an overnight stopover, and the duration of the stopover. What's more, you can also select where you want to have your stopover. Want to say "Hi" to a friend in another city en route to your destination? Or fancy a quick round of shopping? Go Multi-City or Nomad and add places to your search that you wish to visit.