How much is a ticket from Key West to Chicago O'Hare?

Depending on when you travel and how far in advance you book, fares between Key West and Chicago can differ a lot.

Choose a date to explore the best fares now.

If you’re flexible with timing, consider overnight flights — they often cost less and are less crowded. Exploring multiple date and time combinations can help you find the cheapest solution.

Are there multiple airports in Key West and Chicago?

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

• Airports in Key West: Only Key West - International operates in this city.
• Airports in Chicago: 3 airports are available in Chicago - Midway, O'Hare, Rockford.

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.

Plan your journey from Key West to Chicago O'Hare with ease

Use Jetcost to tailor your search — direct or connecting flights, round-trip or one-way, filtered by airline, price, travel time, or agency.

Other popular destinations

Exploring options in United States? These cities are trending: Atlanta, Los Angeles, Miami, New York City, Orlando.

Flight availability can change quickly — refresh the results if you’ve been away from the page for a while.