$128 Find Cheap Flights from Chicago O'Hare Airport to Key West - Compare and Save

When flying from Chicago O'Hare Airport to Key West, you should consider leaving on a Tuesday and avoid Thursdays if you are looking for the best rates. For your return to Chicago O'Hare Airport, you’ll find the best rates on Wednesdays and the most expensive ones on Mondays.

The cheapest month for flights from Chicago O'Hare Intl Airport to Key West is July, where tickets cost $365 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is $540 and $532 respectively.

No, with an average price for the route of $435, prices are generally cheapest when you fly direct.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Key West, you should book around 2 weeks before departure, which saves you about 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

In the past 5 days, the cheapest round-trip tickets from Chicago O'Hare Airport to Key West were found on American Airlines ($309) and Delta ($329).

There are 2 airlines that fly nonstop from Chicago O'Hare Intl Airport to Key West. They are American Airlines and United Airlines. The cheapest airline for this route is United Airlines, with the best round-trip deal found costing $249. On average, the best prices for this route can be found at United Airlines.

Miami (MIA) is the top choice – 46% of KAYAK users who clicked on 1-stop flights from Chicago O'Hare Airport to Key West picked an itinerary connecting there.

Flights via Miami (MIA) offer the most affordable fares, with an average round-trip price of $468.

Consider flying via Atlanta (ATL) for the shortest journey. The average one-way travel time for flights connecting there is 5h 16m.

If you prefer a quick connection, Philadelphia (PHL) often has the shortest layovers from Chicago O'Hare Airport to Key West, with an average of 1h 05m.

There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Each day, there are 2 nonstop flights that take off from Chicago O'Hare Intl Airport and land in Key West, with an average flight time of 3h 21m. The most common departure time is 11:00 am and most flights take off in the morning. Each week, there are 14 flights and there are the same amount of flights each day (2).