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ORD - EYW

$100 Find cheap flights from Chicago O'Hare 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 5/22. 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
Thu 6/13
Thu 6/20

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 42,566,405 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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

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

 
These are the cheapest deals for flights from O'Hare Intl to Key West currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from O'Hare Intl to Key West

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from O'Hare Intl to Key West.

Recent one-way flight deals from O'Hare Intl to Key West

Only flying one-way? Below are some of the best one-way flight deals from O'Hare Intl to Key West found on KAYAK recently.

Recent last minute flight deals from O'Hare Intl to Key West

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from O'Hare Intl to Key West.

Recent direct flight deals from O'Hare Intl to Key West

The latest deals for direct flights from O'Hare Intl to Key West so you can sit back and relax without the need for a layover.

Cheap bus & train deals from O'Hare Intl to Key West

Find recent round-trip train or bus tickets from O'Hare Intl to Key West.

All round-trip flight deals to Key West

The cheapest plane tickets to Key West found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:00 am - 11:47 amORD-EYW
4h 47m1 stop
6:03 pm - 11:54 pmEYW-ORD
6h 51m1 stop
$248Delta
Find Deal
Sat, Jul 27 - Fri, Aug 2
12:22 pm - 7:40 pmORD-EYW
6h 18m1 stop
12:39 pm - 6:44 pmEYW-ORD
7h 05m1 stop
$268Delta
Find Deal
Fri, Jun 21 - Tue, Jun 25
6:00 am - 1:05 pmORD-EYW
6h 05m1 stop
7:00 am - 7:15 pmEYW-ORD
13h 15m2 stops
$281Delta
Find Deal
Mon, Aug 12 - Wed, Aug 21
9:32 am - 5:12 pmORD-EYW
6h 40m1 stop
6:10 pm - 11:54 pmEYW-ORD
6h 44m1 stop
$288Delta
Find Deal
Wed, May 29 - Wed, Jun 5
8:30 am - 3:54 pmORD-EYW
6h 24m1 stop
2:08 pm - 9:20 pmEYW-ORD
8h 12m1 stop
$330American Airlines
Find Deal
Sat, Jul 27 - Sat, Aug 3
9:45 am - 4:29 pmORD-EYW
5h 44m1 stop
2:40 pm - 9:37 pmEYW-ORD
7h 57m1 stop
$345American Airlines
Find Deal
Tue, Jun 11 - Mon, Jun 17
8:05 pm - 4:08 pmORD-EYW
19h 03m2 stops
2:43 pm - 7:05 pmEYW-ORD
29h 22m3 stops
Thu, Jun 27 - Thu, Jul 4
8:05 pm - 4:08 pmORD-EYW
19h 03m2 stops
2:43 pm - 10:01 amEYW-ORD
20h 18m2 stops
Thu, Jun 27 - Thu, Jul 4
6:40 pm - 2:25 pmORD-EYW
18h 45m1 stop
11:30 am - 9:21 amEYW-ORD
22h 51m1 stop
$418United Airlines
Find Deal
Tue, Jun 4 - Thu, Jun 6
2:25 pm - 2:25 pmORD-EYW
23h 00m2 stops
1:05 pm - 11:20 pmEYW-ORD
11h 15m2 stops
$430United Airlines
Find Deal
Wed, May 29 - Tue, Jun 11
6:40 pm - 9:17 amORD-EYW
13h 37m2 stops
Wed, May 22
9:32 am - 5:12 pmORD-EYW
6h 40m1 stop
$159Delta
Find Deal
Thu, May 30
5:37 pm - 4:18 pmORD-EYW
21h 41m2 stops
Wed, Jul 17
7:02 am - 4:18 pmORD-EYW
32h 16m3 stops
Wed, Jul 17
6:40 pm - 2:35 pmORD-EYW
18h 55m1 stop
$217United Airlines
Find Deal
Mon, Jun 17
9:22 am - 5:08 pmORD-EYW
6h 46m1 stop
$254Delta
Find Deal
Wed, Jul 17
7:00 am - 9:55 amORD-EYW
25h 55m2 stops
$257United Airlines
Find Deal
Thu, May 30
5:30 am - 12:06 pmORD-EYW
5h 36m1 stop
$258American Airlines
Find Deal
Thu, Jun 6
5:07 am - 2:06 pmORD-EYW
7h 59m2 stops
$264American Airlines
Find Deal
Thu, Jun 6
6:16 pm - 9:17 amORD-EYW
14h 01m1 stop
Wed, May 22
9:55 am - 5:25 pmORD-EYW
6h 30m1 stop
2:11 pm - 9:29 pmEYW-ORD
8h 18m1 stop
$435American Airlines
Find Deal
Fri, May 17 - Mon, May 20
9:55 am - 5:25 pmORD-EYW
6h 30m1 stop
5:09 pm - 9:29 pmEYW-ORD
5h 20m1 stop
$485American Airlines
Find Deal
Thu, May 16 - Sat, May 18
7:30 am - 3:18 pmORD-EYW
6h 48m2 stops
6:10 pm - 11:59 pmEYW-ORD
6h 49m1 stop
$490American Airlines
Find Deal
Thu, May 16 - Sat, May 18
7:00 am - 5:24 pmORD-EYW
9h 24m1 stop
11:45 am - 9:29 amEYW-ORD
22h 44m1 stop
$637United Airlines
Find Deal
Wed, May 15 - Sun, May 19
9:55 am - 4:08 pmORD-EYW
5h 13m1 stop
2:29 pm - 10:33 pmEYW-ORD
9h 04m1 stop
$672American Airlines
Find Deal
Thu, May 16 - Sun, May 19
7:30 am - 3:18 pmORD-EYW
6h 48m2 stops
2:29 pm - 10:33 pmEYW-ORD
9h 04m1 stop
$677American Airlines
Find Deal
Thu, May 16 - Sun, May 19
2:55 pm - 2:25 pmORD-EYW
22h 30m2 stops
11:45 am - 9:29 amEYW-ORD
22h 44m1 stop
$699United Airlines
Find Deal
Wed, May 15 - Sun, May 19
7:00 am - 4:31 pmORD-EYW
32h 31m3 stops
10:12 am - 6:17 pmEYW-ORD
9h 05m2 stops
Wed, May 15 - Sun, May 19
5:41 pm - 4:31 pmORD-EYW
21h 50m2 stops
10:12 am - 6:17 pmEYW-ORD
9h 05m2 stops
Wed, May 15 - Sun, May 19
7:10 am - 5:12 pmORD-EYW
9h 02m2 stops
7:05 am - 5:01 pmEYW-ORD
10h 56m2 stops
$2,818Delta
Find Deal
Thu, May 16 - Sun, May 19

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 $310 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $529 and $518 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 60 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 $248 on Delta, followed by American Airlines ($330). One-way flight deals have also been found from as low as $159 on Delta and from $217 on United Airlines.

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.

Good to know

Low season

September

High season

January

Cheapest flight

$100
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 13% 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 $100 for a one-way ticket and $248 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?

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

  • What is the most popular layover when flying to Key West from Chicago O'Hare Airport?

    Charlotte is the most popular layover city among KAYAK users traveling from Chicago O'Hare Airport to Key West.

  • 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 $357 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 $469 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 $408 or less round-trip.

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 9152 reviews
7.9Comfort
7.3Entertainment
8.6Crew
7.3Food
8.2Boarding
Airline reviews

They canceled my flight going back to SF after I was at the airport. Wanted me to take a flight 14 hours later. Not a happy camper.

2.0 MediocreRandy, May 2024SEA - SFO
Read more about Alaska Airlines reviews

They canceled my flight going back to SF after I was at the airport. Wanted me to take a flight 14 hours later. Not a happy camper.

I didn’t like not knowing my seat till I got to the airport - and my boarding group was F (last).

I have never flown Alaska Airlines before & would recommend them to anyone& will use again

Flight itself was great! Snacks are never really good; in this case, the "butter braids" and Biscotti cookie were both hard. The attendants' were good. We felt we found a good deal on the cost. The check-in process was very smooth: Alaskan Airlines always does a good job. Boarding was pretty timely, too. We fly Alaskan whenever possible and will continue to do so.

Wasn’t an Alaska plane so the seats were very thinly padded- glad I wasn’t going further.

Service was excellent. Staff at check in cleared hurdles for me so I could travel with my service animal.

Clean plane, relatively spacious in Main Cabin. One experience: I'm 79, with torn rotator cuff (R shoulder). I asked for help getting my carryon into the overhead bin and was told that the staff "does not help with this" (or some such phrase. On previous flights, help has been offered (and accepted). I prevailed on a fellow passenger for this. Also, why not board back to front?? Would this not help in the speed of boarding?

The process was professional and really informative. I personally did not find any issue with thr process from start to finish.

Flight was late but crew was very efficient and friendly.

Not a good experience, we were delayed by an hour due to maintenance issues.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

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.

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

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

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.
5/22Wed
2 stops
13h 37mORD-EYW
$100
5/30Thu
1 stopDelta
6h 40mORD-EYW
$159
7/17Wed
2 stops
21h 41mORD-EYW
$173
7/17Wed
3 stops
32h 16mORD-EYW
$181
6/17Mon
1 stopUnited Airlines
18h 55mORD-EYW
$217
7/17Wed
1 stopDelta
6h 46mORD-EYW
$254
5/30Thu
2 stopsUnited Airlines
25h 55mORD-EYW
$257
6/6Thu
1 stopAmerican Airlines
5h 36mORD-EYW
$258
6/6Thu
2 stopsAmerican Airlines
7h 59mORD-EYW
$264
5/22Wed
1 stop
14h 01mORD-EYW
$266

Search by stops

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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.
5/17Fri
multi-stopAmerican Airlines
6h 30mORD-EYW
5/20Mon
multi-stopAmerican Airlines
8h 18mEYW-ORD
$435
5/16Thu
multi-stopAmerican Airlines
6h 30mORD-EYW
5/18Sat
multi-stopAmerican Airlines
5h 20mEYW-ORD
$485
5/16Thu
multi-stopAmerican Airlines
6h 48mORD-EYW
5/18Sat
multi-stopAmerican Airlines
6h 49mEYW-ORD
$490
5/15Wed
multi-stopUnited Airlines
9h 24mORD-EYW
5/19Sun
multi-stopUnited Airlines
22h 44mEYW-ORD
$637
5/16Thu
multi-stopAmerican Airlines
5h 13mORD-EYW
5/19Sun
multi-stopAmerican Airlines
9h 04mEYW-ORD
$672
5/16Thu
multi-stopAmerican Airlines
6h 48mORD-EYW
5/19Sun
multi-stopAmerican Airlines
9h 04mEYW-ORD
$677
5/15Wed
multi-stopUnited Airlines
22h 30mORD-EYW
5/19Sun
multi-stopUnited Airlines
22h 44mEYW-ORD
$699
5/15Wed
multi-stop
32h 31mORD-EYW
5/19Sun
multi-stop
9h 05mEYW-ORD
$949
5/15Wed
multi-stop
21h 50mORD-EYW
5/19Sun
multi-stop
9h 05mEYW-ORD
$973
5/16Thu
multi-stopDelta
9h 02mORD-EYW
5/19Sun
multi-stopDelta
10h 56mEYW-ORD
$2,818

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Chicago O'Hare Airport - Key West Flights

Departure:

Chicago O'Hare Airport (undefined)United States

Destination:

Key West (EYW)United States

Return flight deals:

Key West - Chicago O'Hare Airport

Cabin classes:

$1,058
$1,053
$754
$342