Cheap flights from Chicago O'Hare Intl Airport to Key West from $153
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to Key West departing on 6/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Key West
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Key West?
In general, September 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 $361. If you are unable to visit Key West during the month of September, then departing from Chicago O'Hare Intl Airport during the month October is also very affordable. Most momondo users find prices during this month for around $398.
What is the cheapest day to depart on your flight to Key West?
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 $362. 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 $552.
What is the cheapest time of day to depart on your flight to Key West?
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 $338. 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 evening, with an average ticket price of $822. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.
What is the cheapest Chicago O'Hare Intl to Key West flight route?
Fly from Chicago O'Hare Intl to Key West for the best Chicago O'Hare Intl - Key West flight prices
How far in advance should I book a flight to Key West?
You are more likely to see cheaper flights to Key West from Chicago O'Hare Intl Airport when booking 7 weeks ahead of your departure date. In general, you can expect to find flights to Key West for around $439 when searching 7 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 $368 on momondo.
What cabin class options are available on Chicago O'Hare Intl to Key West flights?
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.
Can stopping save me money on Chicago O'Hare Intl Airport to Key West flights?
No. A direct flight is the cheapest option for a flight between Chicago O'Hare Intl Airport to Key West.
How have Chicago O'Hare Intl Airport to Key West flight prices changed over time?
As of June 2025, prices for Chicago O'Hare Intl Airport to Key West flights are approximately 7% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Chicago O'Hare Intl to Key West?
United Airlines, Delta, and American Airlines are the most popular carriers operating from Chicago O'Hare Intl to Key West
What airlines fly 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 50% 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.
When to book flights from Chicago O'Hare Intl Airport to Key West
Cheap Chicago O'Hare Intl Airport to Key West (ORD to EYW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Key West
How far is Chicago O'Hare Intl to Key West by plane?
Key West is 1252.7 mi away from Chicago O'Hare Intl. A reasonable flight in good conditions will take 3h 11m.
When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Key West Airport?
Prices for flights from Chicago O'Hare Intl Airport to Key West Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Key West Airport?
The number of operators available for flights from Chicago O'Hare Intl Airport to Key West Airport is 3 as of June 2025.
How old do you have to be to fly from Chicago O'Hare Intl Airport to Key West Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago O'Hare Intl Airport to Key West Airport.
What documentation or ID do you need to fly to Key West Airport?
The required travel and health documents for your Key West Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Key West Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago O'Hare Intl Airport to Key West?
Based on momondo bookings for flights between Chicago O'Hare Intl Airport and Key West, the leading plane model is Embraer 170, making up 48.75% of the total bookings. Other popular models include Boeing 737-700 with 36.67%, Embraer 175 with 5.62%, and Embraer 175 (Enhanced Winglets) with 2.92%.
What is the most popular airline from Chicago O'Hare Intl Airport to Key West?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago O'Hare Intl Airport to Key West is American Airlines (50% of total bookings). The next most popular airlines are United Airlines (45%) and Delta (6%).
Best airlines flying from Chicago O'Hare Intl Airport to Key West
Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Key West with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $216 | Free Cancellation | Rating 8.0 7,950 reviews | |||
| PriceFrom $263 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $283 | Free Cancellation | Rating 7.2 10,000 reviews |
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Why should I use momondo to find a flight deal from Chicago to Key West?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Key West. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Chicago to Key West with flexible booking policies on momondo?
All flight searches from Chicago to Key West on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to Key West?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Key West.
I’m not ready to book a flight from Chicago to Key West right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Key West, momondo offers a useful price alert feature which will track prices for flights to Key West from Chicago and alert you when they change.