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.

Exploring all airports near Key West and Chicago

Checking all the airports available in the area can give you more departure and arrival options for your trip.

• Airports in Key West: Key West - International is currently the only one operating.
• Airports in Chicago: Chicago is served by 3 airports - Midway, O'Hare, Rockford.

Looking at expected traffic to the airport can help avoid surprises on departure day. On busy routes, flying from a quieter airport might also save you money.

Refine your flight search from Key West to Chicago Midway

With Jetcost, it’s easy to narrow down results to find flights that match your schedule and preferences. You can filter by airline, price, trip type, and more — including offers from the best airlines and travel agencies.

Other popular destinations

Also looking at United States? These cities are trending: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Online agencies can show different offers for the same flight — it’s worth comparing. Filters let you narrow things down further, like selecting a specific time slot to find flights that suit you best.