Find out what a flight from Chicago Midway to Key West might cost

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

Select your dates to check current offers.

Try shifting your departure forward or backward by a day to find better options. If you’re looking for a good deal, consider flying outside peak hours as well.

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.

Filter and compare flights from Chicago Midway to Key West

Jetcost helps you manage complex searches with simple filters. Sort by airline, duration, number of stops, or even time windows for outbound and return flights.

Other popular destinations

Want more ideas for your trip to United States? Check these: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Advanced filters help you skip long layovers or inconvenient times. The “airlines” filter is handy if you want to collect miles or prefer a certain onboard experience.