How to estimate the price of a flight from Chicago to Key West?

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

Select your dates to check current offers.

Checking fares across several nearby dates can help you see which days offer the best deals. Jetcost lets you track price changes and grab the best opportunities.

Airport options between Chicago and Key West

Even for routes around 1998 km, using different airports might affect flight cost and travel time.

• Airports in Chicago: You can fly from 3 airports in Chicago - Midway, O'Hare, Rockford.
• Airports in Key West: Key West - International is the only functioning airport.

Checking the average travel time to the airport can help you plan better. For some routes, changing your arrival or departure airport might also affect the price.

Adjust your flight filters for Chicago – Key West

Jetcost gives you tools to search smarter. Pick your ideal price range, airline, departure time, and flight type — then compare offers from agencies like Expedia, eDreams, and more.

Other popular destinations

Planning a trip to United States? These cities are popular too: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Sorting options let you see the most affordable flights first. Some results may include extra fees shown only at checkout — always read carefully to see what’s included.