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

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

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.

Best airport options between Key West and Chicago

If you're open to flying into or out of more than one airport, you’ll have more routes to compare.

• Airports in Key West: Key West - International is the only operating airport.
• Airports in Chicago: In Chicago, 3 airports are available - Midway, O'Hare, Rockford.

Some airports offer extras like lounges, fast track, or self check-in — good to keep in mind. Comparing airports by services offered helps you balance cost and comfort.

Explore flights from Key West to Chicago Midway your way

On Jetcost, you can filter by round-trip or one-way, time of day, airline, number of stops, and even by agency like eDreams or Expedia. Options include Delta, United, American, and more.

Other popular destinations

Also interested in United States? Check out: Las Vegas, Los Angeles, Miami, New York City, Orlando.

If you’re flexible with dates, try checking the days before and after to see if prices vary. Some routes are offered by multiple agencies — comparing fares can really pay off.