ORD - EYW

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

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ORD — EYW
Dec 2 — Dec 91
Round-trip
1 adult
Economy
0 bags
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Fri 12/2
Fri 12/9

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Good to know

Low season

September

High season

March

Cheapest flight

$90

Average price round-trip

$456

Good deal round-trip

$312

Good deal one-way

$512
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Chicago O'Hare Intl to Key West
(avg. price over the last 2 weeks)
or less
or less

When to book flights from Chicago O'Hare Airport to Key West

Estimated round-trip price
Average price per month
Flight prices as travel date approaches

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 $512 or less one-way and $312 or less round-trip.
  • The cheapest flight from Chicago O'Hare Airport to Key West was found 74 days before departure, on average.
  • Book at least 4 weeks before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly is September.
  • Morning departure is around 80% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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

Top airlines flying Chicago O'Hare Intl to Key West

Scores according to KAYAK customer reviews
7.2
American AirlinesOverall score based on 49282 reviews
7.5Boarding
7.1Comfort
7.9Crew
6.9Entertainment
6.7Food
Airline reviews
Cons: "Late and then mechanical issues."
Read more about American Airlines
Cons: "Late and then mechanical issues."
Pros: "Crew was great"
Cons: "Seat was uncomfortable. Flight was much too crowded"
Pros: "Flight was cancelled after multiple delays & I changed to United."
Cons: "Stop delaying & canceling flights, especially last minute"
Pros: "Really easy boarding and flight. Great in flight entertainment options."
Pros: "All was good"
Cons: "Nothing to complain about."
Pros: "Seat assignment process was great and considerate of my preferences."
Cons: "If AA could fix its luggage handling process that would be great. BOTH (!) of my bags have been lost on this flight. Both have been eventually located, recovered and delivered to me, but experience was not pleasant this time."
Pros: "Flight attendants were friendly and thoughtful."
Cons: "Seating is too tight. Hard to believe that in 2019, major airlines still have seats without any electrical or UBS outlets for charging devices."
Pros: "Crew was great."
Cons: "Plane was about 1000 years old and I don’t think I’ve sat in a more uncomfortable seat."
Pros: "Comfortable seats and snack / drinks service"
Cons: "Delayed flight departure and bumpy landing"
Cons: "I was apparently "flagged" by British Airways for extra security checks. As I understood it in London, I was randomly selected for this security check. This then apparently meant that I was to be flagged for all subsequent flights. This meant that in Chicago, after going through two other security checks that day (Zurich and London) and completing customs, I had to engage in a full Homeland security check. This involved removing protective covers from my laptop and phone that were hard to get off (not meant to be taken off regularly) and a full body search that I did not have to do in London. After many hours of traveling, this was very a frustrating experience."
Cons: "I will never, ever book with Kayak again"
Pros: "Flight crew was great. The plane was half full, so the attendants allowed us to move."
Cons: "Terrible landing in Charlotte. The plane was rattling and had an annoying whistle."
Cons: "British Airways/American Airlines lost/delayed luggage again! Then send an email in the middle of night with a link to schedule home delivery of the luggage that was valid for 4 hours only. It is clearly an attempt to cheat out of their responsibility of home delivery of the luggage that was delayed the second time. Poor, poor service by American Airlines."
Cons: "It was not clear that I needed a different 6 letter code to checkin using the AA website. I finally got frustrated and called AA only to find out the code was different. The codes should have been the same or you should have referenced it on the website when I tried to check in"
Cons: "Flight was delayed for more than 4 hours with little communication from staff as to why, gate was changed to a gate across the airport."
Pros: "The boarding was quick and easy as well as the crew was friendly and accommodating. Great end to a fun weekend away."
Pros: "Our plane was late getting to the gate. They kept us informed and turned it around pretty quickly. There were storms between Chicago and Rochester so we were rerouted. As a result the hour flight was an hour and a half. The pilot kept us informed and it was a very smooth flight. So even though I was over an hour late arriving I so appreciated the communications and the safer route. AA seems to be communicating more than other airlines and I appreciate that. Flying is absolutely no fun anymore so you take what you can get for the positives."
Cons: "WiFi wasn’t working so I couldn’t communicate my late arrival to family picking me up."
Cons: "On my first flight from SLC to ORD I asked 3 different American Airlines employees if I needed to pay for my carryon before I got on the plane. They all said no. I got on the plane, put my carryon under the seat in front of me and everything was great. I landed in Chicago, got to my gate, went to board and this very rude employee stopped me after I scanned my ticket and told me I couldn’t board with my bag. The EXACT bag I had boarded with in SLC. After harshly grabbing my bag and putting it in the carryon basket to check for size, she wouldn’t let me pass by her into the boarding bridge and told me I was going to have to pay. I tried explaining that I had asked I’m SLC if I needed to check it and they had all said no and that it fit under my seat. She said, “I don’t care what they said in SL, this is what I’m saying here.” And directed me to the front desk where I had to pay $50!! $50 for a carryon backpack that fit under my seat comfortably 20 minutes before!! Without saying a word (cause I didn’t want to yell at the poor girl behind the desk) I paid the $50 and proceeded to enter the bridge but before I passed through, the rude woman said, “have a nice flight ma’am” and scoffed!! An audible scoff. So I’m short, I hate American Airlines and I will do my BEST to not have to fly with them in the future."
Pros: "The fact that they re-booked without me having to contact customer service."
Cons: "The connecting flight was cancelled while boarding was in progress at the start of the journey."
Cons: "Flight was delayed by untold circumstances causing us to miss our connecting flight to Venice."
Pros: "On time departure and early arrival"
Cons: "Nothing"
Pros: "Nice crew Spacious plane"
Pros: "The crew was amazing, flight was very smooth, arrived early, plane clean, service was great."
Cons: "For being in first class, my seat did not recline so I couldn't sleep and audio for my entertainment center was not working"
Pros: "Good time for flight"
Cons: "Tight, hot inside plane, no refreshments"
Cons: "They left the lights on the whole flight"
Pros: "They alerted me to problems with our flight and we switched to an earlier flight. No problems with new flight. Good service."
Cons: "Great trip"
Pros: "Not turbulence"
Pros: "Was on time."
Cons: "Not eventful."
Pros: "crew was great, plane seemed newer and clean. individual screens worked better than others I've used in flights."
Cons: "newer touch screens were great except viewing angle couldn't be adjusted. standard food was horrible, esp for an international flight; not sure if specialty diets have better meals. kid movies were dubbed into many language options but Chinese was not one for ANY kid films. bathrooms with the same crappy mini sinks that you can't really wash your hands in, esp if someone pukes in it. they should all learn from Japan's ANA airliners with the motion sensor sinks with faucets raised up high enough for you to wash your hands without touching the gross basin."
Pros: "On time, good service."
Cons: "Luggage did not make the transfer on time (Chicago-Charlotte after Tokyo), although they had about 45 minutes to load it. Do not buy an international ticket with less than 1.5 hours transfer time. (It took 45 minutes to get through customs/immigration and retrieve luggage for transfer."
Cons: "Missed it."
Pros: "Nothing"
Cons: "An S80? Really? This plane was older than me! Horrible plane! The crew looked like they had been up since 4 am. Looked exhausted and unfriendly. I do want to clarify that this was an American Airlines operated plane, not etihad."
Cons: "The cramped space"
Cons: "All was excellent! Only the internet was not working good , payed for all flight access but most of the time the internet was not working. Anyway I contacted support team and they refunded me"
Cons: "The flight was delayed more times than I can count, we got a different reason each time. Weather I can understand, but telling us we are waiting on a specific crew to arrive and then announcing that crew is not for our flight was just terrible communication. No one seemed apologetic. The only thing they did was bring a snack cart over for us, and that got raided by children so many people didn't get anything. We had arranged transport from Orlando to Tampa for that evening, and our rides had to cancel because instead of 7pm we were now arriving at 130am. Your airline's mistakes put everyone at an inconvenience and we weren't offered assistance to fix it. My husband went to ask for help in arranging new transport home, but he couldn't even get to the front of the line. The customer service was terrible. We really enjoyed our first leg of the flight home with American Airlines, but after the second leg and all of the problems we had... we will not fly with American Airlines in the future."
Pros: "on time"
Cons: "very cold"
Cons: "This made the check in process extremely frustrating and confusing. Traveling with my elderly dad who had to squeeze between two large men for 7 hours because people who actually booked the airline got priority seating. We had to pay an extra $500 to upgrade to comfortable seats. Not pleased w Kayak."
Pros: "The crew was great and getting 2 meals was very nice."
Cons: "My headphone jack kept malfunctioning (loud popping noises in my earbuds) while watching the movie and all the reading lights came on and stayed on the majority of the flight so sleeping was difficult."
Pros: "An agent found me a window seat for the Chicago-Barcelona leg of the trip with extra leg room. That was amazing. Also, the lost luggage assistant for American Airlines was super helpful and nice. Also, the 787 (I think that was the Chicago-Barcelona craft) was a very enjoyable airplane. It was super smooth. It had high tech windows that adjusted the amount or type of light that could filter through the windows depending on the settings."
Cons: "When I arrived in Barcelona my Bag went missing. It showed up an two hours after my flight landed."
Pros: "I enjoyed the entertainment because I don't watch movies in the theater often. The movies I saw in-flight were recent films I've been wanting to see and made time pass fairly quickly."
Cons: "I'm not a giant, but there definitely was not enough leg room in the main cabin. I could not sit comfortably, especially in the middle seat."
Pros: "Good flight. Arrived on time"
Cons: "Jet bridge was broken and needed repair. Delayed departure."
Pros: "The crew were exceptionally friendly and helpful. They made the negatives about the flight much more bearably be their excellence service whether during boarding, in flight, or after landing."
Cons: "I booked the flight originally through british airways and expected your standard, modern plane for cross atlantic travel. Boarding to find myself on a 767 designed (and likely built) in the 80s was rather disappointing."
Pros: "Gate crew kept the door open as we dashed to our connection and welcomed us by name as they hustled us on board. Ground crew did an amazing job of transferring our luggage in the short 10 minutes or so that we had between planes. Thank you everyone!"
Pros: "Seats were really neither notably comfortable nor notably uncomfortable. I think they were slightly on the comfortable side."
Cons: "Would be nice to have more modern aircraft amenities, like power outlets for device charging, and display screens with at least some complimentary entertainment, or at least flight path tracking. Boarding counter lady was obnoxiously strict about not letting our carry-on bags to be carry-on. She made us test them in the size device and said they were too big, even though they could easy be pushed into the space, and regardless of the fact that we just flew on an American Airlines flight with them as carry-on and were only on a layover with them! Regarding the previous AA agent who let them be carry-on, she said "shame on them." Complete opposite of the positive experience we had with her counterpart in Phoenix. ಠ_ಠ"
Cons: "They cancelled the flight and put me to fly the next day"
Pros: "Everybody was nice my ride was comfortable and they treat me with respect"
Cons: "I like everything"
Pros: "Flight was smooth, boarding was smooth, made good time in the air despite slight delay"
Cons: "We sat on the plane at the gate and then on the tarmac for quite awhile after some delays, but the air conditioning wasn't working. It was incredibly hot, uncomfortable, and I felt sick due to the temperature in the cabin It's just unacceptable to have to sit there in that condition!"
Pros: "My back is probably even more worst than what it is ,I had poor back support...u had to sit up the wholetime and no pillows.Wish you all had reclining seats and a Lil pillow or something.Everytime I travel I'm never comfortable sleeping,if the trip is far."
Cons: "The seats,no cushion ,no pillows."
Pros: "They were friendly. Seats are rarely comfortable..."
Cons: "I think all planes need better leg room...."
Cons: "Everything was good!"
Pros: "The flight was on time and smooth."
Cons: "Too many people with carry on luggage."
Cons: "The Boarding was not fair. The most horrible experience in my life and the Customer Service made me felt like a delinquent."
Pros: "Friendly crew, tasty meals. Comfortable seats"
Pros: "Flight attendants were absolutely amazing!!!!! They made the trip very enjoyable!"
Cons: "Food!"
Pros: "Crew was nice; not out of their way, though."
Cons: "Food, movies, space"
Pros: "Great crew"
Cons: "Very uncomfortable seats"
Pros: "Crew was nice."
Cons: "The entertainment system for an international flight was lacking compared to other airlines."
Pros: "Corralled group lines allowed people to get in line when I was ready versus open entrance for each group"
Cons: "Plane arrived late to gate making my flight arrive in Austin an hour later. I have an ride home, too."
Cons: "Delayed Swiss flight 8 tue 12 dec 2017 led to catastrophe"
Pros: "Quick"
Pros: "Comfortable Flight"
Cons: "Inflight WI-FI doesn’t work, it kept on dropping in the middle of the movie or it went back to the beginning. Couldn’t see a movie."
Pros: "Nothing! I will make sure to never use United for any flight from now on."
Cons: "Everything! The customer service was terrible and cold. Non refundable tickets should state in huge red writing that they are non refundable!!!"
Cons: "You better get rid of basic economy."
Pros: "No delay, friendly crew"
Pros: "Boarding was fine, no delays. Crew was nice, no complaints there! I had an empty seat next to me, so could stretch out. Luckily I brought a blanket with me, since I know from previous experience it's always too cold on planes."
Cons: "The entertainment didn't work on my iPad or my iPhone. I kept getting an error. Also, the WIFI is way too expensive."
Cons: "United has new seats that have absolutely no leg room and are very uncomfortable. I will make sure never to fly United again. This was 3 hours of agony."
Pros: "Associates were nice and knowledgeable. The airplanes were comfortable. Love the onetime performance of scheduling."
Cons: "Unite Airline performance wasn't the good. Also, there was nobody in Chicago to help us with the transferring process."
Pros: "I had the exit window and that made a huge difference in my trip as I am a 6ft tall woman who is all legs."
Cons: "It was slightly turbulent and TSA at O'hare airport are the rudest and laziest humans on the planet."
Pros: "Snacks and drink"
Cons: "Average"
Pros: "Flight was on time."
Cons: "Seats are uncomfortable and cramped."
Cons: "The pilot's landing was way too fast. I was sure that the plane would come to a stop in Hwy 280 at the end of the Asheville runway. That plane probably needed a major brake job after that landing. We ended up at the absolute very end of the runway!"
Pros: "Wasn't thrown off"
Cons: "Another delayed flight with United"
Cons: "They might as well have thrown us in a car trunk the crew was very unaccommodating they didn't really care about us and the room legroom is ridiculously smal. On the connecting flight, the last flight the plane was two thirds empty and the crew made us sit in our assigned seats, crammed together telling us that if we want to sit in a seat with more legroom we have to pay $180"
Cons: "Too many seats too close together. The entire trip was too hot and stuffy. The flight attendants showed minimal care about the uncomfortable hot and stuffy environment."
Cons: "The United mobile app as well as my emails stated that the gate was B3. Upon arriving at gate B3 and attempting to board, I was alerted that I was at the incorrect gate. The gate was switched to C11. However, my app did not alert me nore did it reflect the gate change. I didn't receive a text or email update. I had to run to the different concourse nearly missing the fling."
Pros: "Crew was lovely."
Cons: "Seats BARELY reclined, and leg room was minimal. The whole flight was very uncomfortable even for someone who's only 5'3" who flys regularly. Also, no in flight entertainment for a long flight. Total fail."
Cons: "Turbulence was insane"
Pros: "We'll coordinated."
Cons: "The seats were terribly uncomfortable (including her flight to Chicago). The cushion made me slide down the seat and could not get comfortable."
Pros: "My flight in was smooth, seamless and amazing. The crew was so lovely."
Cons: "My flight out was a shot show that included a four hour delay and frantic running to gate changes. The staff was very unhelpful. The snack was awful."
Cons: "I went on this trip as an veterinary humanitarian out reach. I was also guardian to one high school student so that she might have an experience of such to guild her future. Her flight was missed booked to leave after mine, I attempted to rebook my flight with Luthansia but they would not let me me even partial rebook. I attempted a number of times to rebook the flight but their solution was extreme financial gain for them when more reasonable alternative could have been arranged. They canceled my entire return flight and left me stranded. I had to piece together a return flight on a shoe string budget. Thankfully American Airlines was understanding for it appears Luthansia and United are not."
Pros: "In flight entertainment worked. Staff was friendly."
Cons: "I had no issue with the delay, things happen. I was dealing with a knee injury and the gate plan had us all over the airport. It was quite frustrating to get to a gate in another terminal only to get told we were being moved back to the terminal we had just come from! Then that gate was changed again, involving another long walk on said bad knee!"
Pros: "The promptness on the flight -the friendly crew - arriving on time means the most, also the flight itself was smooth"
Cons: "There were no ticketing agents at the gate adding an hour to the flight."
Cons: "2.5 hour delay. No working bathrooms. Couldn't hear the tv and headphones that they gave out were useless."
Pros: "The crew was awesome and the flight wasn't bad at all"
Cons: "It was suggested that I didn't bring my carry on with me so I left it to be voluntarily checked and it came back ripped"
Cons: "flight was delayed for over 5 hours and gate was changed over 6 times"
Pros: "Over all it was a great flight aside from the rain delay but that's Mother Nature for you"
Cons: "Flight was delayed due to severl technical issues. Crew at least offer free drinks or snacks for the five hour delay."
Pros: "Nice clean planes and seat, on time performance"
Cons: "The flight attendant was hard to understand"
Pros: "Nothing"
Cons: "I was angry that I had to fly to Houston before heading to Phoenix which made my arrival in AZ much later than I had planned. My flight had been rescheduled since I missed my flight the night before because the first flight had been delayed. So the new flight was a longer trip because of the extra layover. The overall flight was a mess."
Pros: "Nothing"
Cons: "Multiple delays and gate changes; chaotic boarding; shabby plane condition (bathroom looked held together with duct tape)."
Pros: "That the plane actually took off and landed fine."
Cons: "Flight delayed almost 2 hours. I booked this flight on this airline as my previous flight on a different airline was delayed over 7 hours."
Pros: "Nice crew and boarding staff. The plane was repaired rather than the flight being cancelled."
Cons: "No airconditioning on the ground so the extra time on the tarmac was very uncomfortable. While taxiing, a screen went blank, so the plane returned to the terminal, deplaned, and there was a two hour delay for the repair."
Pros: "Tons of food and water. Movies good. Staff on plane were excellent. Clean bathrooms and peacful. Nice that headphones were provided."
Cons: "Seats should not be set to go back so far, if a person in front sets back all way, no space passenger behind. The seats should be calibrated to go back less of an angle."
Cons: "Some inspector idiot decided that the exterior cover stickers weren't "up to code" literally half an hour before my flight, delaying us 2 hours. I got onto a different flight at the last second, then the same thing happened to that plane. Brilliant on their parts. I almost lost a job interview thanks to your people."
Cons: "Boarding went quickly but then waited almost 35 minutes on the plane to take off. Once the plane landed there was again a wait to pull into the gate. Spent more time waiting on the plane than the flight itself."
Cons: "This flight was also delayed. It was bade enough the first flight was delayed almost an hour, but this flight also left late from the gate."

Book cheap flights from Chicago O'Hare Airport to Key West

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1/10Tue
1 stopMultiple Airlines
9h 50mORD-EYW
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16h 42mEYW-ORD
$240
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$242
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$245
4/11Tue
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3h 48mORD-EYW
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3h 30mEYW-ORD
$248
1/10Tue
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$254
3/29Wed
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5h 42mORD-EYW
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3h 30mEYW-ORD
$255
4/11Tue
1 stopAmerican Airlines
5h 42mORD-EYW
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$256
1/7Sat
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$257
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1/21Sat
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1/24Tue
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1/10Tue
nonstopUnited Airlines
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12/18Sun
1 stopUnited Airlines
24h 00mORD-EYW
12/25Sun
nonstopUnited Airlines
3h 27mEYW-ORD
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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:

$1,216
$1,497
$1,916
$226

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