How much is a flight from Key West to Chicago?

Prices vary based on date, airline, and availability. Compare several options if you're flying between Key West and Chicago.

Pick a travel date to see today’s available fares.

Fares change often — checking several times throughout the week can make a big difference. Booking in advance often means access to lower prices for the Key West - Chicago route.

Are there multiple airports in Key West and Chicago?

If your departure or arrival city has more than one airport, it's worth comparing all of them for timing and pricing.

• Airports in Key West: Only Key West - International operates in this city.
• Airports in Chicago: 3 airports are available in Chicago - Midway, O'Hare, Rockford.

If you're traveling with a group or bulky luggage, look into parking or transport options. Alternative airports may offer faster transfers or better rates.

Flight filters for the route Key West – Chicago

Customize your search on Jetcost to focus only on flights that suit your needs. Whether you want a direct connection, specific airline, or shorter layover, filters help you find it faster.

Other popular destinations

Flights to United States are often searched alongside: Las Vegas, Los Angeles, Miami, New York City, Orlando.

The cheapest flights might leave at odd hours or arrive at less central airports — keep that in mind. If you travel often, you can always select your trusted airlines from the available options.