Cheap flights from Chicago to Key West

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How much is a flight from Chicago to Key West?

There’s no fixed price — fares between Chicago and Key West can vary a lot by day or time.

Pick a travel date to see today’s available fares.

Flying during the week can be more affordable, as weekend flights tend to be pricier. Also consider demand and availability: the last remaining seats often come at higher fares!

Flying between Chicago and Key West? Consider these airports

Depending on your destination and where you’re starting from, it might make sense to look beyond the main hubs.

  • Airports in Chicago: Chicago has 3 airports - Midway, O'Hare, Rockford.
  • Airports in Key West: The only active option is Key West - International.

Check if your destination airport has a rail link — it can make getting around easier. Jetcost lets you view options from all Chicago airports in a single search.

Explore flights from Chicago to Key West your way

On Jetcost, you can filter by round-trip or one-way, time of day, airline, number of stops, and even by specific travel agency.

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.
Frequently Asked Questions

Frequently asked questions about flights from Chicago to Key West.

How much does an airline ticket from Chicago to Key West cost?

Flight prices can vary a lot depending on the period and destination. At the moment, this information is not available for flights from Chicago to Key West.

How far is Chicago from Key West?

Chicago is about 1998 km from Key West.

What are the airports in Key West?

Key West has one airport: Key West - International.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the most popular cities in United States?

The most popular cities in United States according to our users' searches are: Las Vegas, Los Angeles, Miami, New York City, Orlando.

When should I book a flight from Chicago to Key West?

The best time to book a flight from Chicago to Key West is 1 month in advance, while the worst time is 1 week in advance.

What is the cheapest month to fly from Chicago to Key West?

This information is not available at the moment.

What is the most expensive month to fly from Chicago to Key West?

This information is not available at the moment.

What is the best day of the week to fly from Chicago to Key West?

This information is not available at the moment.