Cheap flights from Chicago O'Hare Intl Airport to Key West from $110

In general, August 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 $329. If you are unable to visit Key West during the month of August, 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 $377.

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 $366. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Thursday, 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 $515.

According to our data, the cheapest time of day to fly to Key West is at noon. momondo users have found flights departing from Chicago O'Hare Intl Airport to Key West at noon for as low as $439. 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 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 $428 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 $416 on momondo.

There are 4 cabin classes available to choose from on Chicago O'Hare Intl Airport 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 23% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Key West flight.

As of October 2026, 1 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 11:00AM, with 100% of daily flights taking off at noon.

As of October 2026, there are 8 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 25% of flights taking off on this day.