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ORD - EYW

$103 Find cheap flights from Chicago O'Hare Intl Airport to Key West

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Key West departing on 7/17. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
vie. 5/24
vie. 5/31

Search hundreds of travel sites at once for deals on flights to Key West

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Key West, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Key West, as well as popular online travel agencies
In the last 7 days travelers have searched 45,119,101 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from O'Hare Intl to Key West (ORD-EYW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Key West that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:00 am - 1:49 pmORD-EYW
5h 49m1 stop
2:44 pm - 6:49 pmEYW-ORD
5h 05m1 stop
$216Delta
Find Deal
mar., jul. 16 - mar., jul. 23
6:15 am - 12:06 pmORD-EYW
4h 51m1 stop
5:04 pm - 10:34 pmEYW-ORD
6h 30m1 stop
$226American Airlines
Find Deal
mié., jun. 5 - mié., jun. 12
7:05 am - 1:20 pmORD-EYW
5h 15m1 stop
6:00 pm - 11:59 pmEYW-ORD
6h 59m1 stop
$232Delta
Find Deal
lun., jul. 1 - jue., jul. 4
7:30 am - 4:08 pmORD-EYW
7h 38m1 stop
5:09 pm - 11:59 pmEYW-ORD
7h 50m1 stop
$245American Airlines
Find Deal
mié., may. 15 - mié., may. 22
8:20 am - 3:08 pmORD-EYW
5h 48m1 stop
5:06 pm - 10:10 pmEYW-ORD
6h 04m1 stop
$246American Airlines
Find Deal
mié., ago. 21 - jue., ago. 29
7:10 am - 1:05 pmORD-EYW
4h 55m1 stop
7:00 am - 11:24 amEYW-ORD
5h 24m1 stop
$248Delta
Find Deal
mar., ago. 27 - dom., sep. 1
6:15 am - 12:06 pmORD-EYW
4h 51m1 stop
5:47 pm - 11:58 pmEYW-ORD
7h 11m2 stops
$250American Airlines
Find Deal
mié., jun. 5 - mié., jun. 12
8:10 am - 4:29 pmORD-EYW
7h 19m2 stops
12:46 pm - 5:32 pmEYW-ORD
5h 46m1 stop
$251American Airlines
Find Deal
lun., jul. 1 - jue., jul. 4
6:00 am - 2:09 pmORD-EYW
7h 09m1 stop
11:45 am - 9:51 amEYW-ORD
23h 06m1 stop
$398United Airlines
Find Deal
mié., ago. 14 - dom., ago. 18
6:00 am - 2:37 pmORD-EYW
7h 37m1 stop
8:10 pm - 9:35 amEYW-ORD
14h 25m1 stop
$427United Airlines
Find Deal
jue., oct. 17 - dom., oct. 20

Flights from O'Hare Intl to Key West - Travel Insights & Trends

Get data-powered insights and trends into flights from O'Hare Intl to Key West to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Key West?

The average price of all flights from Chicago O'Hare Intl Airport to Key West clicked on KAYAK for each day over the last 12 months.
For Chicago O'Hare Airport to Key West, Tuesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Key West back to Chicago O'Hare Airport, the best deals are generally found on Wednesday, with Saturday being the most expensive.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Key West?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago O'Hare Intl Airport to Key West, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago O'Hare Intl Airport to Key West is August, where tickets cost $308 on average. On the other hand, the most expensive months are March and February, where the average cost of tickets is $600 and $531 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Key West?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago O'Hare Intl Airport to Key West, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago O'Hare Intl Airport to Key West, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 82 days before departure.

Which airlines provide the cheapest flights from Chicago O'Hare Airport to Key West?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago O'Hare Airport to Key West found by KAYAK users in the last 72 hours was for $216 on Delta, followed by American Airlines ($226). One-way flight deals have also been found from as low as $103 on American Airlines and from $220 on United Airlines.

Which airlines fly non-stop between Chicago O'Hare Intl Airport and Key West?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago O'Hare Intl Airport to Key West.
There is just one airline that flies from Chicago O'Hare Intl Airport to Key West direct and that is American Airlines. The best one-way deal found from American Airlines for the route is $225.

How many flights are there between Chicago O'Hare Intl Airport and Key West per day?

There is a maximum of 1 nonstop flight a day that takes off from Chicago O'Hare Intl Airport and lands in Key West, with an average flight time of 3h 14m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 7 flights.

Which cabin class options are there for flights between Chicago O'Hare Intl Airport and Key West?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 3 cabin class options for the route. These are First, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago O'Hare Airport to Key West take?

Direct flights take on average 3h 05m to travel the 1,253 miles between Chicago O'Hare Airport and Key West.

What’s the earliest departure time from Chicago O'Hare Airport to Key West?

Early birds can take the earliest flight from Chicago O'Hare Intl Airport at 8:20 am and will be landing in Key West at 12:34 pm.

What’s the latest departure time from Chicago O'Hare Airport to Key West?

If you prefer to fly at night, the latest flight from Chicago O'Hare Intl Airport to Key West jets off at 10:58 am and lands at 3:03 pm.

Good to know

Low season

September

High season

January

Cheapest flight

$103
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Chicago O'Hare Airport to Key West

When to book flights from O'Hare Intl to Key West

Are your dates flexible? Find out the best times to travel from O'Hare Intl to Key West based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago O'Hare Airport to Key West flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Key West?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Key West was $103 for a one-way ticket and $216 for a round-trip.

  • Do I need a passport to fly between Chicago O'Hare Airport and Key West?

    A passport is not required to fly from Chicago O'Hare Airport to Key West.

  • Which airlines offer Wi-Fi service onboard planes from Chicago O'Hare Airport to Key West?

    American Airlines, and PSA Airlines offer inflight Wi-Fi service on the Chicago O'Hare Airport to Key West flight route.

  • Which aircraft models fly most regularly from Chicago O'Hare Airport to Key West?

    The Embraer 170 is the aircraft model that flies most regularly on the Chicago O'Hare Airport to Key West flight route.

  • Which airline alliances offer flights from Chicago O'Hare Airport to Key West?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago O'Hare Airport and Key West, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago O'Hare Airport to Key West?

    There are nonstop flights from Chicago O'Hare Airport to Key West on a daily basis.

  • Which is the best airline for flights from Chicago to Key West, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Key West are Delta and United Airlines. With an average price for the route of $382 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $470 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Key West?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago O'Hare Airport to Key West.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Key West?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Key West from Chicago O'Hare Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago O'Hare Airport to Key West?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Key West with an airline and back to Chicago O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and EYW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to Key West?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Key West from Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from ORD to Key West

  • Looking for a cheap flight? 25% of our users found flights on this route for $249 or less one-way and $388 or less round-trip.

Prefer to fly non-stop from Chicago O'Hare Airport to Key West?

Find which airlines fly direct from O'Hare Intl to Key West, which days they fly and book direct flights.

Nonstop departures

Chicago O'Hare Intl to Key West

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines

American Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Nonstop returns

Key West to Chicago O'Hare Intl

Monday

American Airlines, Qatar Airways, United Airlines

American Airlines, Qatar Airways, +1 more

Tuesday

American Airlines, Qatar Airways, United Airlines

American Airlines, Qatar Airways, +1 more

Wednesday

American Airlines, Qatar Airways, United Airlines

American Airlines, Qatar Airways, +1 more

Thursday

American Airlines, Qatar Airways, United Airlines

American Airlines, Qatar Airways, +1 more

Friday

American Airlines, Qatar Airways, United Airlines

American Airlines, Qatar Airways, +1 more

Saturday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Sunday

American Airlines, Qatar Airways, United Airlines

American Airlines, Qatar Airways, +1 more

See more direct flights
See more direct flights

Top 4 airlines serving from O'Hare Intl to Key West

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Key West. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from O'Hare Intl to Key West? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 9110 reviews
8.6crew
7.3food
7.3entertainment
8.2boarding
7.9comfort
Airline reviews

Flight was good. Glad it was delayed or I may have missed the connection since I got to Seattle at about the same time my connection was to leave. The snack was a small bag of pretzels and a small soda. Can’t really call that food. There was no entertainment available on the flight.

8.0 ExcellentAnonymous, Apr 2024SEA - TUS
Read more about Alaska Airlines reviews

Flight was good. Glad it was delayed or I may have missed the connection since I got to Seattle at about the same time my connection was to leave. The snack was a small bag of pretzels and a small soda. Can’t really call that food. There was no entertainment available on the flight.

It was much better than expected. Short flight and smaller plane so no entertainment or food.

It was so easy to board using my boarding pass on my iPhone, and I liked what I was given on the plane for food and drink, and everyone was very friendly.

It took around two hours to depart. Just sitting in the tamarack waiting. It impacted my traveling plans in a very dramatic way. When we returned, it took around two hours for us to be able to get our luggage. Ridiculous!!

The messaging about the change in flight destination and options for getting to SFO was poor. There should have been frequent updates. When I spoke to the boarding agent moment before we were supposed to board, he was flippant and offered no help before the announcement was made that transportation would be arranged. It was as poor of an experience that I've ever had.

I thought every thing was good with the acceptation of the long layover between Seattle and the Tampa trip.

My plane ride down landed 20 min late. Boarding at SFO was strange too. The people at the terminal were nice—but, boarding lacked direction, and was confusing . Coming back was worse—the plane was hours behind—and I barely caught the last Bart train back to San Francisco (3 min more and I would have been in trouble). It was a very stressful trip, and it didn’t need to be.

Same as the earlier flight. Bad boarding practices, uncomfortable seats, and no Wi-Fi service.

While the flight and the legroom was good boarding took a long time. The different groups Boarding made no sense as those in the back of the flight boarded last causing delays as people try to find room for their luggage in the upper bins. While there were plenty of seats on the flights We were spaced so that some rows were filled and others were empty. My first flight was very crowded and uncomfortable. On the way back both flights did not have Wi-Fi nor the entertainment package. We were only made aware of this a few hours before the flight. Since the flight was in the morning, I was asleep and was not able to download Books or other media to my phone. This is my first time flying Alaska airlines and I will admit to thinking twice before I do so again.

Our flight was delayed by six hours, our plane never left Portland the night before but the airline didn’t inform anyone till two hours before a six am flight. The plane, our plane never left the west coast! No plane no flight, simply let folks know when you know, not hours and hours later. No one apologized, no one said much of anything, we were just expected to wait quietly and await instructions.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Seat back monitors and outlets were dead and not working.

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Boarding super slow with people allowed to linger in aisles

There were choices for the snacks. Good choices and tasty lunch and breakfast as well.

First time travel in economy and the worst experience I ever had ! Shame on paying 600 dollars to be in a tuna can ! Service was terrible no even water no even class no even matters your flight attendants were lazy and sloppy very bad experience! After all these years traveling in first and once I try this cause I need to go to a destination for an emergency wow shame on you !

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Unfortunately our flight was delayed by 45 minutes due to Kate arriving aircraft. Once we stated everything was great.

For some strange reason I was put in zone 5 for boarding even though I had paid premium price for a premium seat right behind business class. This must have been a flaw because everyone else around me in the same zone (row) had been placed in zone 3.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We sat on the plane for 1 hour because the airline was short handed could not be unloading.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Book cheap flights from Chicago to Key West

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Key West found on KAYAK in the last 72 hours.
7/17mié.
1 stopAmerican Airlines
5h 09mORD-EYW
$103
5/14mar.
1 stopUnited Airlines
26h 42mORD-EYW
$220
7/17mié.
2 stopsAmerican Airlines
8h 15mORD-EYW
$236
9/2lun.
1 stopAmerican Airlines
6h 40mORD-EYW
$252
6/6jue.
1 stopAmerican Airlines
5h 46mORD-EYW
$253
5/23jue.
1 stopAmerican Airlines
7h 51mORD-EYW
$254
9/2lun.
2 stopsAmerican Airlines
6h 35mORD-EYW
$257
5/14mar.
2 stopsAmerican Airlines
6h 48mORD-EYW
$258
7/17mié.
3 stops
13h 35mORD-EYW
$358
4/29lun.
1 stopUnited Airlines
14h 35mORD-EYW
$418

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Last minute flights from O'Hare Intl to Key West

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Key West that are departing in the next 10 days.
4/25jue.
nonstopAmerican Airlines
3h 14mORD-EYW
5/1mié.
nonstopAmerican Airlines
3h 25mEYW-ORD
$409
4/27sáb.
nonstopAmerican Airlines
3h 14mORD-EYW
4/29lun.
multi-stopAmerican Airlines
8h 10mEYW-ORD
$417
4/27sáb.
nonstopAmerican Airlines
3h 14mORD-EYW
4/30mar.
multi-stopAmerican Airlines
6h 54mEYW-ORD
$418
4/27sáb.
multi-stopAmerican Airlines
5h 10mORD-EYW
5/4sáb.
multi-stopAmerican Airlines
6h 00mEYW-ORD
$425
4/26vie.
multi-stopDelta
7h 15mORD-EYW
5/1mié.
multi-stopDelta
6h 23mEYW-ORD
$428
4/26vie.
multi-stopDelta
7h 15mORD-EYW
4/27sáb.
multi-stopDelta
6h 05mEYW-ORD
$478
4/27sáb.
multi-stopUnited Airlines
8h 05mORD-EYW
5/1mié.
nonstopUnited Airlines
3h 28mEYW-ORD
$498
4/27sáb.
multi-stopUnited Airlines
9h 40mORD-EYW
5/1mié.
multi-stopUnited Airlines
7h 33mEYW-ORD
$513
4/27sáb.
multi-stop
16h 09mORD-EYW
4/29lun.
multi-stop
13h 27mEYW-ORD
$530
4/27sáb.
multi-stop
16h 49mORD-EYW
4/29lun.
multi-stop
13h 27mEYW-ORD
$562

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Chicago O'Hare Airport - Key West Flights

Departure:

Chicago O'Hare Airport (ORD)United States

Destination:

Key West (EYW)United States

Return flight deals:

Key West - Chicago O'Hare Airport

Cabin classes:

$2,368
$1,053
$754
$176