Cheap flights from Chicago to Key West from $136

In general, August is the cheapest month to fly from Chicago to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $364. If you are unable to visit Key West during the month of August, then departing from Chicago during the month July is also very affordable. Most momondo users find prices during this month for around $373.

On average, the least expensive day to fly to Key West from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $362. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Key West for around $511.

According to our data, the cheapest time of day to fly to Key West is in the morning. momondo users have found flights departing from Chicago to Key West in the morning for as low as $447. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Key West are more costly in the afternoon, with an average ticket price of $449. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

Fly from Chicago O'Hare Intl to Key West for the best Chicago - Key West flight prices

You are more likely to see cheaper flights to Key West from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Key West for around $425 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Key West from Chicago for as low as $398 on momondo.

There are 4 cabin classes available to choose from on Chicago to Key West flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 32% on your flight if you consider stops on a Chicago to Key West flight.

As of September 2026, prices for Chicago to Key West flights are approximately 37% more expensive when compared to flights at the same time last year.

United Airlines and Delta are the most popular carriers operating from Chicago to Key West

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Key West from Chicago according to our data. American Airlines is the first choice among our users, with 56% of people opting to fly with this airline when traveling to Key West. Keep in mind that there are 3 different airlines that fly to Key West on a routine basis, so you have a few additional options to choose from.