Planning a flight from Chicago Midway to Key West?

Flight prices from Chicago to Key West change depending on demand and time of booking.

The lowest fare seen in the past 15 days was €339.

Many users find better fares by booking several weeks in advance. In fact, for many routes, booking early is one of the best ways to save.

Are there multiple airports in Chicago and Key West?

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

• Airports in Chicago: 3 airports are active in Chicago - Midway, O'Hare, Rockford.
• Airports in Key West: Key West - International is the only airport currently running.

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.

Find the best flight from Chicago Midway to Key West

With Jetcost, you can filter results by flight time, airline, price range, and layovers. Choose direct or connecting flights, round-trip or one-way, and compare offers from Ryanair, Easyjet, British Airways, and more.

Other popular destinations

Searching for flights to United States? Travelers also looked at: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Use filters to exclude options that don’t match your budget or travel preferences and personalize your search for Chicago Midway – Key West flights.