CHI - EYW

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CHI — EYW
Sep 29 — Oct 61
Round-trip
1 adult
Economy
0 bags
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Thu 9/29
Thu 10/6

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Good to know

Low season

September

High season

March

Cheapest flight

$120

Average price round-trip

$455

Good deal round-trip

$431

Good deal one-way

$283
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Chicago to Key West
(avg. price over the last 2 weeks)
or less
or less

When to book flights from Chicago to Key West

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

Top tips for finding a cheap flight out of Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $283 or less one-way and $431 or less round-trip.
  • The cheapest flight from Chicago to Key West was found 61 days before departure, on average.
  • Book at least 3 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 15% 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 flights from Chicago to Key West

Top airlines flying Chicago to Key West

Scores according to KAYAK customer reviews
7.9
DeltaOverall score based on 31457 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.5Food
Airline reviews

All was well on this flight.

Read more about Delta

All was well on this flight.

All staff very friendly and accommodating

It was orderly and on time and the staff was friendly.

Cons: "Wearing a mask was difficult."
Pros: "Great crew."
Pros: "Crew not so much!"
Cons: "A bit friendlier ...had no ice??"
Pros: "Good"
Pros: "I have used Delta long time. Used to be really bad. Today. Good good."
Cons: "Free beer"
Pros: "Exit row seating for no extra charge"
Cons: "Seat mate not friendly"
Pros: "Safe and fast journey."
Cons: "Vegan options for everything."
Pros: "pilot was great... made the landing at key west seem easy!"
Cons: "Flight attendants seemed to really like their jobs!"
Pros: "Entertainment was good and there was a choice of food."
Cons: "The crew sucked."
Pros: "surprisingly spacious seats. plane felt brand new. on screen entertainment was great, and relieved to have charging inputs for my device in the seat."
Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."
Pros: "The website delivered everything I needed."
Cons: "More discounts for frequent users."
Pros: "great crew!"
Cons: "luggage. what a nightmare. I waited 30min for my luggage (after a delayed flight) only to be told by a fellow PASSENGER that some of our luggage was directed to a FRONTIER CAROUSEL. I then had to wait by that carousel till I found it. so much for "bags in 20min guaranteed""
Pros: "Entertainment choices were plentiful."
Cons: "The flight attendants were borderline rude. No eye contact, no smile, not helpful when asking a question (overhead compartments were full in my section; I asked what I should do, response: „ I don’t know either“ and walked off. I went to find a spot further up the aisle..."
Cons: "Not enough seat room on plane. Hot not enough air flow"
Pros: "the people were Awesome!!flight crew were very personable and easy to get along with, as well as get in touch with."
Cons: "where to start, I am not a huge overweight person. I have 26-28" shoulders and longer legs then most 5'-10" people have. That said, you should not be required to hold your arm out and hold the seat back in front of you so that you are not elbowing or shouldering the people beside you. sitting sideways on a seat I paid extra for doesn't seem like a great flight to me."
Cons: "At least one hour late"
Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."
Pros: "The movies kept my daughter busy."
Pros: "Pleasant."
Cons: "It was scheduled so late at night."
Cons: "My flight was delayed, which would have caused me to miss my connecting flight. The customer service person was not at all helpful, and told me there were no other flights available on any airline until the next day. However, I was able to go online and book another flight immediately...which means that she was either being disingenuous or actively undermining efforts to get me home in a timely fashion. Very disappointing and as a SkyMiles member would have thought there would be some level of common courtesy dealing with a non-weather related delay that drastically impacted my travel plans."
Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."
Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"
Pros: "Once we hit the coast we skirted down the coas of Florida which provided a spectacular view. The approach and landing at Key West airport was thrilling and absolutely perfect. We’ve flown Delta many times but this was our first but not last time to Key West."
Cons: "Nothing"
Pros: "spacious comfortable seats"
Cons: "I waited in line at Virgin Australia for 35 minutes only to be told that I was actually on a Delta flight even though my itinerary said Virgin Australia. good thing I was early to airport or I would of missed my flight because I had to go find Delta check in"
Pros: "My experience with Delta was excellent. Everything from checking in, boarding, flight, and landing was simple. Everyone I came into contact with was extremely helpful and courteous."
Pros: "Our Delta plane was brand spanking new. Everything worked and the inflight entertainment system was fantastic with many movies to choose from, free headphones, games, tv shows, etc. The crew was polite and the seating at least as comfortable as expected for a 4 hour flight."
Cons: "The restrooms in the rear of the plane were remarkably small, even by airline standards. I'm a somewhat larger person and I fit, but I know a lot of people who would literally not be able to fit on the toilet without touching both of the sidewalls or risk getting stuck in there. The boarding process at San Jose Del Cabo was the most ridiculous setup I've ever experienced. There were numerous flights boarding out of the same gates and at least 3 or 4 lines for different destinations forming on a ramp just outside the gates. There were guys with signs trying to herd people into the correct lines and then loading the people onto buses which took you out to the planes. The planes were loading from both the front and rear doors and people were getting tangled up inside because of the haphazard loading process. Very easy for a person to end up on an incorrect plane!!"
Pros: "Delta seats are comfortable and media ststem is good."
Cons: "Flight was late and the staff wasn't kind Neither at JFK gate neither on both flights. Looks like they are doing you a favor to listen to you when you ask them something."
Pros: "What can I say...I love Delta!"
Pros: "Smooth and easy."
Cons: "Not applicable"
Pros: "On time departure; good updates by flight deck; luggage arrived unscathed."
Cons: "Once beverage service was complete, flight attendants retreated to the back of the plane. On a 4-hour flight, it would have been nice to have someone come by and ask if we needed anything, such as water, coffee, or juice. Granola bar was good."
Cons: "Hard to get comfortable even in easy comfort but easy comfort is better than typica arats."
Cons: "Late flt"
Pros: "Staff hospitality"
Cons: "Deboarding delay, seems typical"
Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."
Pros: "Great entertainment, good food, nice staff."
Cons: "You have to pay for the ckecked baggage ($25 per piece) and the airfare was not cheap."
Pros: "The staff was great. The plane was the cleanest of MD-88s I'd been on recently."
Cons: "The old plans have your too cramped or squeezed in. The connecting flight from ATL to MKE made this one look good."
Pros: "Ease in finding another connecting flight get to Miami when our connection was delayed."
Cons: "Time between connection should be 2+ hours"
Pros: "Food in first class was quite good. Flight was smooth, and arrived early."
Cons: "The boarding agents lost control of the crowd form the get go. The first class cabin crew on our side of the plane was inattentive, though it appeared on the other half of the plane the crew was very attentive. This is one of the poorer first class seats in the industry. The "lie flat" seat is just that, a lie. It is pitched at an angle, though not as steep as some. Foot cubby is narrow and constrictive, bordering on claustrophobic."
Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."
Cons: "The "Delta Comfort" seats were not comfortable: the armrest didn't raise, so the seats were narrow. The handle of our suitcase got broken."
Pros: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."
Pros: "Both the crew in the plane and the groundcrew were helpful. Particularly the people in Key West, in terms of finding our luggage and helping us get a taxi."
Cons: "Offer offer healthier food choices, and larger amounts for beverages, particularly water."
Pros: "Some entertaining choices but not all clear which ones were in my flight"
Cons: "The food I wanted had sold out by the time I ordered it"
Pros: "Aisle seat; leaving on time"
Cons: "Sat next to family with 3 small children; kids and parents did very well. Wished Delta could have arrange for family to have 3 seats together. Would have been family friendly."
Pros: "The plane ROCKED"
Cons: "The crew on this flight were very "eh", no smiles or anything, just handing coffee and snacks out to burdensome passengers"
Cons: "Plane was late for no particular reason, uncomfortable seats, small leg room, cheap entertainment system, crew forgot my meal."
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: "Free upgrade to business class"
Cons: "Nothing"
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: "Overall service at was very satisfactory on all the sectors. In-flight service was excellent. Lounges were good at Mumbai and Frankfurt. Pl. see my comments about United lounge at Chicago."
Cons: "I was denied an entry to the UNITED LOUNGE at Chicago Air port. The lady stated that this lounge is only for the departing passengers! She scanned my boarding card.and I said to her that I am departing to Detroit. She said I can enter if I am a GOLD card member or purchase a day pass for $59.00. I declined. I am under the impression that United is a partner of Lufthansa.and that they should honor the same Business class privileges as Lufthansa. I found it rather discriminatory act on the part of this particular employee of the United lounge at Chicago airport. Pl. bring it to the attention of the Lufthansa and United . I will appreciate follow up on this matter."
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: "Because we missed our connecting flight with United, we had to fly American from Dallas to Cancun."
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: "The crew of this flight were amazing, attentive, and so positive. They certainly made the long flight an enjoyable one. The only challenge was that the in-flight entertainment stopped working 5 hours into the flight. That said, the crew informed us of how United would compensate us for that. As for the landing, that was perfect. We eased onto the tarmac so gently it barely felt as though we had landed."
Cons: "I wasn't too excited that the in-flight entertainment quit working about five hours in, but the crew did their best to remedy the situation. It did stink that we were delayed in disembarking, but that wasn't the fault of the crew. Lastly, I do wish that food came complimentary with it being a 9-hour flight. The options presented were tasty looking but it felt a little like we were being nickeled and dimed."
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."
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: "The crew was very nice, the plane seating and room was comfortable, no complaints."

Book cheap flights from Chicago to Key West

Recent round-trip flight deals

10/18Tue
1 stopMultiple Airlines
11h 36mORD-EYW
10/19Wed
1 stopMultiple Airlines
16h 00mEYW-ORD
$228
1/11Wed
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8h 22mORD-EYW
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3h 28mEYW-ORD
$257
1/7Sat
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3h 28mEYW-ORD
$259
10/23Sun
1 stopDelta
6h 05mMDW-EYW
10/28Fri
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5h 45mEYW-MDW
$266
1/21Sat
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8h 37mORD-EYW
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7h 20mEYW-ORD
$266
1/7Sat
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7h 22mORD-EYW
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6h 56mEYW-ORD
$268
10/18Tue
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$281
10/23Sun
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6h 25mORD-EYW
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6h 42mEYW-ORD
$282
1/3Tue
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10/15Sat
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11/1Tue
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1/8Sun
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8h 29mORD-EYW
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$300
1/21Sat
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3h 10mORD-EYW
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11/4Fri
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$305
1/10Tue
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10/25Tue
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12/7Wed
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12/10Sat
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11/1Tue
1 stopDelta
5h 11mMDW-EYW
11/9Wed
1 stopDelta
6h 53mEYW-MDW
$322

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21h 34mORD-EYW
$120
12/14Wed
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16h 24mORD-EYW
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11/1Tue
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11/16Wed
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11/18Fri
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21h 44mORD-EYW
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10/11Tue
1 stopMultiple Airlines
13h 57mMDW-EYW
$191
11/26Sat
1 stopMultiple Airlines
17h 28mMDW-EYW
$192
10/18Tue
2 stopsUnited Airlines
22h 05mORD-EYW
$223
12/19Mon
nonstopUnited Airlines
3h 22mORD-EYW
$244
11/1Tue
1 stopDelta
4h 30mMDW-EYW
$253
12/19Mon
1 stopDelta
6h 05mMDW-EYW
$309
11/21Mon
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9h 04mMDW-EYW
$328
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2 stopsDelta
6h 45mMDW-EYW
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Flights to Key West

Destination:

Key West (EYW)United States

Return flight deals:

Key West - Chicago

Cabin classes:

$639
$1,255
$2,046
$278

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