What’s the price of flying from Chicago Midway to Key West?

It depends. Prices for flights from Chicago to Key West fluctuate based on several factors.

The lowest fare seen in the past 15 days was $134.

Checking flights with stopovers can sometimes lead to big savings, especially on longer routes. Also, airfare often depends on availability — it’s wise to track price changes regularly.

Which airports are most convenient between Chicago and Key West?

Whether it’s cost or connection time, the right airport combination can make a difference.

• Airports in Chicago: There are 3 airports in Chicago - Midway, O'Hare, Rockford.
• Airports in Key West: Key West - International is the only functioning airport for now.

In some cases, flying into a secondary airport can also reduce transfer costs. Connections from multiple airports give you more flight options and airlines.

Find flights from Chicago Midway to Key West that suit your schedule

Use Jetcost to sort and filter results based on your preferred flight time, number of stops, price range, or airline. View deals from Delta, United, American, and booking sites like Expedia and eDreams.

Other popular destinations

Interested in United States? These cities are also in demand: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Connecting flights can be cheaper but often mean longer layovers. You can easily select either direct or connecting flights with a single click using the filters.