Cheap flights from Chicago O'Hare Intl Airport to Key West from $92

In general, June is the cheapest month to fly from Chicago O'Hare Intl Airport to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $352. If you are unable to visit Key West during the month of June, then departing from Chicago O'Hare Intl Airport during the month July is also very affordable. Most momondo users find prices during this month for around $363.

On average, the least expensive day to fly to Key West from Chicago O'Hare Intl Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $385. 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 O'Hare Intl Airport to Key West for around $530.

According to our data, the cheapest time of day to fly to Key West is in the afternoon. momondo users have found flights departing from Chicago O'Hare Intl Airport to Key West in the afternoon for as low as $460. 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 at noon, with an average ticket price of $471. Departure times at noon 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 O'Hare Intl - Key West flight prices

You are more likely to see cheaper flights to Key West from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Key West for around $429 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 O'Hare Intl Airport for as low as $366 on momondo.

There are 3 cabin classes available to choose from on Chicago O'Hare Intl 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 6% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Key West flight.

Spirit Airlines and Delta are the most popular carriers operating from Chicago O'Hare Intl to Key West

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Key West from Chicago O'Hare Intl Airport according to our data. American Airlines is the first choice among our users, with 57% of people opting to fly with this airline when traveling to Key West. Keep in mind that there are 4 different airlines that fly to Key West on a routine basis, so you have a few additional options to choose from.

Atlanta (ATL) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Atlanta (ATL) offer the lowest average round-trip price of $196.

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 4h 54m.

Charlotte (CLT) has the shortest average layover time for this route: 1h 19m.

As of February 2026, 3 flights take off from Chicago O'Hare Intl Airport and land in Key West each day. The most common flight departure time for this route is 10:00AM, with 100% of daily flights taking off at noon.

As of February 2026, there are 25 flights per week flying from Chicago O'Hare Intl Airport to Key West. The most common day of the week flights depart is Mon, with 16% of flights taking off on this day.