Find cheap flights from Chicago to Key West

CHI - EYW

Find cheap flights from Chicago to Key West

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Chicago (CHI)
Key West
Fri 1/15
Fri 1/22
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Good to know

Low season

August Best time to beat the crowds with an average 19% drop in price.

High season

December Most popular time to fly with an average 18% increase in price.

Average price round-trip

$428 (avg. price over the last 2 weeks)

Good deal round-trip

$299 or less

Good deal one-way

$212 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
-1 day
-2 days

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $212 or less one-way and $299 or less round-trip.
  • The cheapest flight from Chicago to Key West was found 56 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November, December and January. The cheapest month to fly is August.
  • Morning departure is around 96% 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

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Top 4 airlines serving Chicago to Key West

Scores according to KAYAK customer reviews

8.1
JetBlue
Overall score based on 19,351 reviews
8.3
Boarding
8.2
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews

Pros: "Service was awesome, 100% recommended"

Pros: "Seat space for each passenger"

Pros: "crew was supportive. wifi in the flight"
Cons: "the wait time and the boarding, off boarding of the flight. No electricity in the aircraft."

Pros: "Nothing!"
Cons: "IT WAS TWO BOURS LATE!"

Pros: "More leg room Affordable prices Snacks dunkin donut coffee Pleasant flight attendant Punctuality"
Cons: "Nothing"

Pros: "This flight is 3 + hours delayed, and I think it’s because Jet Blue didn’t have a full flight for the 8:30 am departure, this is unacceptable and I need to be compensated for my time Winston White"
Cons: "This flight is 3 + hours delayed, and I think it’s because Jet Blue didn’t have a full flight for the 8:30 am departure, this is unacceptable and I need to be compensated for my time Winston White"

Pros: "The crew talked a big game. They were ready for anything, including loss of cabin pressure, paid snacks, and even a water landing."
Cons: "No water landing! I was excited to float around on a hot day, go down an awesome slide, and catch some sick waves, but come on people, we never even got a chance!"

Cons: "could not make it in time. Then we got on plane and pilot said it was an electrical problem on the flight but the generators were now up and at em again. Very hair raising ride for me - got in at 2:30 am with another hour to drive home - and I lost a LOT of confidence which I have always had in Jet Blue. I hope this is not the future we can expect with you"

Pros: "How easy it was to board"
Cons: "When I asked if there was any chance I could sit with my family they were nice enough to change are setting. Just a thought if the setting is random when you check in for your flight somewhere the computer should at least work with putting the last names together just a thought."

Pros: "The crews were very friendly A lot of options from direct tv and other entertainment programs The seats were wide enough Free Wifi"
Cons: "The plane got 2 hours delayed The screen was too small There was no charger on the plane Food option was limited"

Pros: "Entertainment, food, crew, and cleanliness were 100000% on point. Loved it."
Cons: "Turbulence and the flight was longer than necessary because we had to go around bad weather. Not the fault of JetBlue!"

Pros: "Cheerful, efficient service. No hidden costs. Free gate to gate WiFi. Comfortable seats. Never flown them before and they are now at the top of my list."
Cons: "Nothing yet."

Pros: "The seats were comfortable."
Cons: "Flight was very late leaving Chicago. We sat on the plane for quite a while (over 30 min) shut up tight with little air circulation AND no information about why we were not leaving the gate. Flight crew were not very friendly - almost "marched" up and down the aisle and barked at people."

Pros: "Adequate leg room and ability to take a carry on we if your extra charge"

Pros: "Easy boarding, friendly staff, nice choice of snacks and beverages. The JetBlue app is very useful."
Cons: "My in flight entertainment never worked. All I had available to look at was the JetBlue commercial channel showing me all of the entertainment I wasn’t able to watch. Not even the live view map worked. One of the attendants said something about resetting the system but I didn’t notice a change. I said something to one of the attendants a little later and she tried doing a reset again, but still no success. I could see other screens working fine and people were watching various programs while I just stared at a static map of the continental United States. Oh well, at least I was able to stream Netflix because of the free inflight WiFi."

Pros: "comfortable seats TV great beverages--actually get can or bottle"
Cons: "when we checked it, did not put us together"

Cons: "The flight was delayed and we would have missed our connection in NYC. So we had to cancel the trip."

Pros: "Good snacks, entertainment and excellent WiFi. Boarding was efficient and seats were comfortable."

Cons: "We arrived later for almost 2 hours"

Pros: "Per usual crew and plan itself were nice"
Cons: "Flight was delayed about 3 hours from scheduled take off"

Cons: "my flight was delayed for 2 hours and there was no compensation for it"

Pros: "Our flight attendant Jeramy was FABULOUS!!"

Pros: "The comfort of the seats are amazing. I was able to sleep through almost all of the flight."

Pros: "Bring her own earphones as then u can listen to their varied entertainment channels. Gave free snacks & there was quite an assortment so I wasn’t stuck w pretzels again. Free soft drinks; nice flight attendants & smooth ride from Chicago to NY"

Pros: "No gate, waited 2 hours in plane"

Cons: "Late boarding with little communication. Equipment failure delayed the flight after pushing from the gate. Additional delay of 10 mins one we got to the destination gate."

Pros: "Everything is ok"
Cons: "Not a thing"

Cons: "When I scanned my boarding pass the Jetblue staff member told me my carry on was too big and had to be checked. This was puzzling to me because I travel often and do not have a problem with that bag. As I was sitting on the plane I saw everyone's bag's were bigger especially the man next to me. His was significantly larger and he had a large duffle bag between his legs causing him to manspread into my area. and yet i was told "make sure your purse is under the seat" seriously?! What about his giant duffle bag and huge carry on roller?!"

Pros: "Captain and crew"
Cons: "Luggage handling"

Pros: "You took great care of my wife who needed a wheelchair. the flight itself was delayed due to weather. I totally understand. I love the extra legroom"

Cons: "Movies didn't work and we were one hour delayed on the runway."

Pros: "The only good things about this flight were: - The crew at the gate were very friendly and attentive - We arrived safely without incident"
Cons: "We were delayed 2 times before boarding. We were delayed 1 more time while on the plane. The pilot told us there was equipment trouble that had been fixed, but there was paperwork to fill out and it would only be a few minutes...and then radio silence for 30 minutes before pulling back. The flight attendants rushed through the pre-flight announcents and I could only understand about 60% of it due to speed, volume and accent. Despite asking me for my drink order, it never came...and I only heard a few soda cans pop open at all. Did they just decide not to serve us? She even gave me a napkin for it. Luckily when they put the snack basket in front of me, there was a tiny bottle of water, which I grabbed...little did I know, that was all I would get. The flight attendants were just tapping in the back of the plane the rest of the flight. They didn’t even bother collecting garbage until we were on final approach. They also never did the normal checks before landing."

Cons: "flight was delayed 2 hours :("

Pros: "Crew was happy and friendly"
Cons: "Can’t think of anything"

Pros: "They refund me the money"
Cons: "I almost lost my international connection, had to pay double to get my destination on time"

Pros: "Ez check in with kiosk"
Cons: "I would like to see an organic food option, even with a fee if necessary. Recommendation, fruit like banana or apple. Certified organic."

Pros: "Boarding system efficient. Lots of leg room. Choice of snacks. Good service."

Pros: "Entertainment on board"
Cons: "My flights was delayed"

Pros: "Gave me my refund!"
Cons: "Flight was delayed 5 times without sufficient reason. Weather was clear. Had to ask for a refund after the 6th delay. Missed an important event."

Pros: "Extra leg room"
Cons: "On both legs of our vacation, going and coming we experienced long delays , 2 hours Boston.to Vhicago and 3 hours Chicago to Boston"

Pros: "This was my first time with JetBlue and I was pleasantly surprised with the size of the plane. It was pretty comfortable"

Pros: "Friendly staff and the on board entertainment and snacks"
Cons: "The last time I took JetBlue the flight was delayed by almost 3 hours"

Cons: "Both ways my flight was significantly delayed. Although Jet Blue sent me notices, none of those came before I was on my way to the airport."

Pros: "L.L Bean crew was amazing!! The tv channels and movies!!"

Pros: "the plane was good!"
Cons: "the plane boarded late"

Cons: "waiting for my luggage"

Pros: "Crew was great. Captain provided lots of updates and provided useful site information prior to landing"
Cons: "TV kept on blacking out"

Pros: "The staff is great, the seats are comfortable, and the food is good"

Pros: "Very helpful customer service, really appreciate their help."
Cons: "I took two JetBlue flights within 4 days, both with delays > 2 hr for mechanical issues. I can count on one hand the number of times I've been significantly delayed in the past 5 years, especially when not in the winter. JetBlue, please fix whatever is wrong with your planes. I've otherwise had nothing but positive experiences with them."

Pros: "Short lines"
Cons: "Seating arrangements"

Cons: "The carrots were hard and the bread was cold."

Pros: "Comfortable plane due to few passengers"
Cons: "7 hour delay after flight postponed."

Cons: "I would ask that the gate does not share in detail reason for delay in seat assignment is related to getting a family sitting together when the basic rules should apply unilaterally."

Pros: "Got to my destination without any issues"
Cons: "Seats/seating area are too small, and I'm not a big person."

Pros: "No"
Cons: "The flight was delayed almost 6 hours, the crew was rude and the “comfort +” seats had very little leg room ."

Pros: "pilot was great... made the landing at key west seem easy!"
Cons: "Flight attendants seemed to really like their jobs!"

Pros: "The flight was on time, the crew was pleasant and looked like they enjoyed working in the air."
Cons: "Our second time on a 787 Dreamliner across the Atlantic as about the same as the the first. The seat pitch is very tight so when a passenger reclines into the next row the seatback nearly touches your face. The Dreamliner seats seem to be very hard and it's difficult to get comfortable."

Cons: "Flight was delayed a bit due to a couple passenger booking/misc issues. 1st class didn’t get gate bevfood service. Oven was busted so my meal wasn’t available. Entertainment console had all channels functional except — not really an issue I just really wanted to have ESPN playing in the background"

Pros: "Son got wings, so was happy."
Cons: "No entertainment."

Cons: "It was late"

Pros: "Crew was nice and welcoming"
Cons: "Well, if our plane had been leaving on time it would've been superb."

Pros: "N/A"
Cons: "Chinese Eastern did not try to help and solve my problem."

Pros: "There was a bit of a mixup in boarding the plane but otherwise the flight was good. There was no entertainment system on this short flight. The flight attendants were very pleasant & efficient. They only served snacks on this short flight but were very good at ensuring everyone had at least one or more beverages. The premium seats were very comfortable ."

Pros: "Short flight"
Cons: "Flight attendant was not willing to go above and beyond as he stated he would. My husband asked for a coke and the flight attendant told him he could only get water."

Pros: "On time departure/arrival despite weather in Atlanta. Always a fan of free messaging and choice of snacks."
Cons: "Delta needs to invest in their gate area at ORD. Understand it’s not a hub but it’s a key business/leisure destination. The MD-80s are ok for a short hop but over 1 hour unless you’re in Comfort+, it’s tight."

Pros: "Snacks, cleanliness and crew"
Cons: "N/A"

Cons: "From the begging they changed the flights for something totally different. It was a 14 hour trip. Awful"

Pros: "Nothing"
Cons: "They take them forever to find me another fly ,make miss my other fly, my work my time and my sleep"

Pros: "It was a normal flight as well expected."

Pros: "I was with my friend"
Cons: "Delayed 12+ hours"

Pros: "We had a 2 1/2 delay due to mechanical issues but the crews, flight and ground, did a great job. Thanks."

Pros: "I was given a complimentary upgrade."

Pros: "The crew and pilot were absolutely amazing."
Cons: "This is my 3rd delta flight in a row that has been delayed. I understand these things happen, just extremely frustrating."

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"

Cons: "It takes time and worries to find the air train and Aeroflot registration."

Pros: "My flight was great. Boarding was easy and the seats were comfortable."

Pros: "The service was amazing , the staff was honestly friendly and nice"

Pros: "What can I say...I love Delta!"

Pros: "Great service, nice agent friendly"

Pros: "Very friendly and professional gate agent and flight attendant"

Cons: "I was unable to fly at all due to a spelling error on my ticket. The airline refused to alter the ticket. Worst experience of my life, ruined my Christmas"

Pros: "Very nice flight and attentive staff. Enjoyed the view of NYC as we flew up the East River, then looped over Nassau County to approach LGA."
Cons: "The male flight attendant who handed out the complimentary drinks and snacks acted a bit strangely. I was very thirsty, and I asked him if I could keep the rest of the can of soda. He neither said yes nor no, but rather completely ignored what I said and just poured my drink and moved on. I was a mildly annoyed, but figured maybe it was policy and he was shy and didn't want to debate the matter. When he took care of the older couple behind us, however, things got really strange. He asked them whether they wanted pretzels or peanuts, but they misheard him and asked for a ginger ale. I happened to know that he did have ginger ale, since my wife had just gotten one, but rather than just pouring the old folks a drink, he repeated himself. "Peanuts or pretzels?" They misheard again and asked him whether he had a diet ginger ale. Again, rather than just pour them the drink, he repeated himself. "Peanuts or pretzels?" This went round and round a few more times -- like a poorly designed computer UI that refuses to accept anything except the correct input -- before the old couple finally figured out the disconnect and picked their snacks before their drinks. Very weird."

Cons: "Layover"

Pros: "Short flight"
Cons: "Too cold Not friendly boarding agent"

Pros: "N/A"
Cons: "2.5 hour delay for no apparent reason at first (supposed mechanical issues with plane) and then waited on plane at gate for a missing pilot who never got picked up from his airport and got stuck in Chicago traffic trying to get to O'Hare. Eventually had to take pilot from another flight before leaving at 8:45 when flight was scheduled for 6:00am."

Cons: "Had a death in the family and no one would help me get back home"

Pros: "Seats were comfortable. Snacks!!! Nice flight crew."
Cons: "I liked everything."

Pros: "The Gogo Inflight wifi and entertainment did not work for even a minute. I choose flights based on their amenities and this one had offered full WIFI service which swayed me to choose to fly with Delta. I'm not sure who is to blame about this issue but I'm pretty frustrated that it was completely dysfunctional."

Cons: "Plane was sat broken at gate and needed part to be flown in. 150 minutes delayed. Not acceptable."

Pros: "I missed my flight for the first time and I was having a complete meltdown at the check in desk until the sweetest agent said "oh no worries sweetheart, let's find you another flight back home"... It seems so simple but with the morning I had, this simple act had me in tears! The kindness and patience she showed me was amazing and definitely the reason I will always fly Delta to any and every destination they are able to take me! <3"

Pros: "No fee to get on an earlier flught"
Cons: "When I tried to rebook online this flight was not an option"

Cons: "I am a 5'3" 125# woman who, unfortunately, had a middle seat assignment. The passenger to my right, on the aisle, weighed approximately 375# and took up 1/3 of my seat. The arm was not able to go down comfortably, and when it did it was not usable . The passenger on my left, window seat, was probably 6'7" and had to sit with a man spread in order to fit. I could not move and was extremely uncomfortable. The plane was overbooked so I was unable to move. Therefore, worst flight ever. Plus, I paid for a full seat and was only able to occupy half of it."

Pros: "Staff hospitality"
Cons: "Deboarding delay, seems typical"

Pros: "The in-flight service was good."

Pros: "Nothing"
Cons: "Poor hospitality by alaska airline staff, especially by MrPavel at gate H4, 01nov2016, prior boarding around 0730am"

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: "Small plane. Very good service. Did not suffer through the crazy multi level boarding calls that some airlines have. No super secret airline clubs that board first. Flying into the Marine terminal is the best part of the trip."
Cons: "The wifi didn't seem to work at all on the plane."

Pros: "Excellent"

Pros: "Easy boarding, plane was on time and the crew was very nice. We came in very hot because key west is a small airport but it was pretty fun!"
Cons: "Seats were old and dated and there was no entertainment offered."

Pros: "Everything was great. Easy boarding great comfortable seating and friendly efficient stewardship"

Cons: "Boarding was a little chaotic. Could have been more organized."

Pros: "staff was amazing, entertainment great, dasani sparkling lime water tasty, very clean and reasonably comfortable"
Cons: "the breakfast was made of 90% sugar - this was very disappointing."

Pros: "Everything was on time!"

Cons: "The flight was cancelled. I didn't receive a refund or free hotel accommodations. I've been on flights in Africa where free hotel accommodations were standard for a layover over 3 hours. A little embarrassing that an airline in America can't afford a hotel for people stranded in a city overnight."

Pros: "I got the vegetarian meal I asked for."
Cons: "Flight was delayed, because of the boarding process with immigration"

Pros: "This flight left about 90 minutes late again due to weather issues. The crew was excellent which made this long flight enjoyable."

Pros: "Staff extremely friendly and helpful"
Cons: "Old plane with no individual tv screens!!! Didn't know these planes still existed!"

Pros: "Extra blanket and pillow. Empty seat to sleep in. Fairly clean interior for the most part."

Pros: "Flight attendants were nice"
Cons: "The seats were incredibly uncomfortable. There was no leg room and 122 of the space below the seat in front of me was taken up by a metal box attached to the seat. I couldn't put both feet under the seat in front of me. The food was bad tasting and overly processed. We were fed a lean cuisine. The entertainment was from mounted tv's in the aisle. At this point, all planes crossing the ocean should have individual tvs for a customer to watch. They had this 15 years ago, how do they not have it now."

Pros: "Flights lately have been a huge disappointment but American Airlines was great! Crew was so pleasant and helpful,food was good and the "entertainment" was too! I'll definitely fly with them again!"

Pros: "All good! Nice staff. Easy travel."

Pros: "The crew was very efficient and friendly while handling everyone. Flight was smooth, food was good. I went to the wrong terminal and did not know that the advertised finair flight was actually American Airlines, the AA ticket counter attendant went all out to make sure I made it to the gate. All this with less than an hour before departure."
Cons: "I went to the wrong terminal, the email ticket had finair in large print and in smaller print indicated American. Luckily I was able to literally run and make my flight. Would be better to more clearly indicate actual airline."

Cons: "Small seats, no wifi, no chargers, terrible entertainment."

Pros: "Once we got on the plane, everything was pretty standard"
Cons: "Flight was delayed 5 hours."

Pros: "The water was clean"
Cons: "Everything else! We were first sold a British airlines flight, and then we got switched to American Airlines. I don't know if that is actually an okay thing for them to do. When we got onto to plane we were stuck on the runway for over 2 1/2 hours, where the outside temperature was 95 degrees and the AC in the plane didn't work. The delay was all due to a mechanical difficulty with the engine, this did not give us peace of mind when flying over the atlantic. while up in the air my newly wedded wife and I were hoping maybe we could watch a movie to help keep our minds off the creaking of the wings, the pool of sweat from the delay, and the grumpy flight attendants. Seeing as it was a 9 hour international flight, you would have expected some sort of entertainment. Maybe a personal TV.... nope. Maybe a community TV... nope. At least they have to have a radio....... nope. All we got were our two thumbs to twiddle. After a much needed nap. We woke up hoping maybe for a hot breakfast, but to put the cherry on top of some terrible ice cream, we got a mediocre cold breakfast. All in all I will not fly American Airlines again. I would happily and quickly pay double for any other airlines but them. It's such a poor reprisentation of our country."

Cons: "Old plane with no plug-ins and outdated media."

Pros: "Staff on the plane were nice."
Cons: "5 hour delay, fear of cancellation ruining a trip planned for years, not feeling we were told what was happening, series of delays extending decision time, unappetizing sandwiches during delay."

Pros: "Free alcohol and good passenger friends and friendly service."
Cons: "No outlets for phones"

Pros: "All the movies"
Cons: "Legroom"

Cons: "Could not read paper when passenger in front reclined seat. No space between rows."

Cons: "My flight was actually processed under American Airlines. Oddly, the confirmation email stated it was Finnair."

Pros: "On time"
Cons: "Cramped seats. Entertainment system outdated"

Cons: "Plane was too old, flight attendants were rude"

Pros: "The departure time. This left enough time to get to the airport and go through security without rushing!"
Cons: "Sitting in the middle Paying for luggage ( I wish Southwest flew out of ORD)"

Cons: "No complaints."

Cons: "Boarding seemed extremely unorganized. Crew skipped group 2 when calling groups to board, resulting in a mad rush."

Cons: "Due to two flight delays, I traveled an additional 24 hours, on top of my 20 hour original flight. Albuquerque Airline staff were rude, dismissive, incompetent, and each individual I spoke with gave me wildly differing information. The two delays (leading to approximately 48 hours of travel) would have been stressful enough, but the callous, ignorant and unprofessional attitudes of American Airlines staff (and staff in general at Chicago O'Hare Airport) really disappointed me. This was even more striking compared with the professional service I received from British Airways (from whom I purchased the tickets). I was ashamed that my country could lag so far behind in terms of basic customer service and problem solving."

Cons: "Requested for wheelchair assistance but none provided?!!"

Pros: "Timing and transit time was excellent"

Pros: "Everything."
Cons: "Nothing."

Cons: "Food was horribe and no dedicated tv per seat"

Cons: "We were delayed for 6 hours due to a maintenance issue. Horrible customer service"

Cons: "Always a problem with these guys"

Pros: "Couldn't of been more impressed especially after being hung out by Southwest!!!"

Cons: "We have flown to Europe recently on SAS and that airline was so much more comfortable than airberlin. Things we missed: personal TVs on the seats, good leg room (airberlin was quite cramped), and small attentions like a disposable towelette. I got no sleep on airberlin."

Pros: "Staff was very friendly and helpful"
Cons: "Experienced 4 hour delay with mechanical and weather problems. But glad they put safety first"

Pros: "They put safety first"
Cons: "Frustrating 4 hour delay"

Cons: "I am very disappointed in my flight. I am 6'7 and paid for an exit row seat. When I got to the airport they gave me a different seat with no leg room. They told me they changed planes and there was nothing they could do to help me. I tried again at the gate and again nothing. Will never fly again."

Cons: "The flight attendants were rude, they had no dinner, no healthy breakfast options, they rationed the beverages and after being without enough water for 12 hours, they would give you dirty looks when you asked for a second serving of plain water."

Pros: "Room on flight in coach was sufficient and im 6 ft 2"

Pros: "The entertainment was pretty good . There was a good variety of movies and music"
Cons: "the cabin was extremely small, absolutely no leg dpace unless you were in first class, specially if you are a taller person."

Pros: "Overall pleasant experience."
Cons: "I was not aware that the FinnAir flight was being handled by American. I missed it when reading my itinerary and had a brief panic when I showed up to the international terminal and my flight was not even listed on the board. Perhaps it could be written a little larger? Thanks."

Pros: "Good value"
Cons: "Poor food quality"

Cons: "That small space!! This is a long flight and you have no room to move around at all!!!!!"

Pros: "Appreciated that the cre didn't wake me to give me my landing card. They did make sure I got one though."

Cons: "I didn't get vegetarian food that I ordered over the phone and I did made sure that it said vegetarian Jain meal on the ticket that I printed. Very disappointed because no point ordering then. I paid $1234 for the trip. And I am traveling because of funeral."

Cons: "Seats too tight. No room"

Pros: "Food, entertainment and free checked bag. Can ask for more!"

Pros: "In flight service."
Cons: "The first check in kiosk associate was turning us away because we reached 30 minutes prior to scheduled departure. However, by then they knew that they were going to be at least 1 hour 30 minute late. Then when kayak emailed us about the delay, the check in people let us in. Ultimately the flight was three hours late."

Pros: "Flight was on time."

Pros: "Flight itself was fine. Major delay resulted in arriving one day later than planned, additional transportation cost, unplanned, and unplanned parking fees. No travel voucher was offered and when I asked was told it was not possible to issue a travel voucher."

Pros: "The flight was good..."
Cons: "No entertainment was available ... even do they announced ..."

Pros: "In flight entertainment. Was able to watch a movie for free."

Pros: "Flight on time and arrived early"

Pros: "That I finally got there a day later. I only had carry on bags, so they weren't lost."
Cons: "At OHare the gate agent sent me to the wrong gate and plane for my flight. I did not arrive Thursday at 8:30 pm as scheduled. Customer service put me on "red eye" to Dulles for the next flight to Charleston, without motel or meal vouchers. I couldnt sleep on the benches there due to asthma and diabetic issues. I arrived Friday 2:30 pm 17 hours late. Dulles overnight cleaning staff helped more than agents at OHare."

Pros: "Good crew"
Cons: "Shitty seats was very uncomfortable probably won't fly United just because of that... Delta has a lot more comfortable seats"

Pros: "Seats were nice and crew was friendly"
Cons: "It wasn't their fault but we did have to land at a different airport due to weather, but it showed that the crew took safety first"

Pros: "Excellent service and friendly staff"
Cons: "Absolutely not enough room to stretch your legs"

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."

Pros: "same as above"
Cons: "same as above"

Pros: "Getting to Charlotte"
Cons: "Plane dirty. Windows dirty. Extremely bumpy. Seats clostraphobic. Sat too long leaving"

Pros: "The flight crew apologized and kept everyone informed."
Cons: "The plane was having mechanical problems. Once it was determined that the problem couldn't be fixed it took the airline quite some time to locate a new plane. They should have started working to identify a new plane sooner. Ended up arriving in Portland after 3 am."

Pros: "Overall fine"

Pros: "flight was excellent"
Cons: "Monitor kept running commercials and a show i couldn't hear very annoying"

Cons: "It would have been helpful if hanging a garment bag were available, which was the case on my return flights to DC on American Airlines."

Pros: "On point"
Cons: "Excellent"

Pros: "The seats were perfect, a lot of leg room. Comfortable side pillows on the seats"
Cons: "All the rest including the absence of food"

Cons: "Why should I have to pay to watch tv? I know you don't have to pay on Southwest, Virgin America or Jet Blue. Not sure that a very (and I mean VERY SMALL) snack can be considered food"

Pros: "On time, gates were close together"

Pros: "Comfy environment, not completely booked plane"
Cons: "The price for one little bottle of Rum, highway robbery I say."

Cons: "The plane was delayed."

Pros: "Newer plane. Very nice staff"
Cons: "Floor around seat was dirty. Lot of exaggerated braking. Suggested a new pilot perhaps?"

Pros: "Getting from point a to point b."
Cons: "Lack of good free snacks. Not getting free bag checked."

Cons: "Deverted to Newark to get to portland"

Pros: "Duration of flight was shorter than expected. Arrived at destination fifteen minutes early."
Cons: "No complaints."

Pros: "Good"

Cons: "Delayed because there was no crew to fly the plane switched gates 6 different time other than that everything was good"

Pros: "I was incredibly disappointed that my luggage got sent on an earlier flight to Memphis from Chicago. When I arrived in Memphis after 24 hours of flying, I found my luggage locked up and no representative to be found. Exhausted, frustrated, and seeing my luggage through the glass door and not being able to retreave it, I was incredibly frustrated with United. If you are going to send luggage on a different flight, be there and available to let travelers claim their luggage. My entire flight had gotten their bags from baggage claim before I even found someone available to open the door. I had to get an American Airlines representative to call them to the area twice before they arrived. If you are going to do this, offer the traveler to be on the earlier flight too. I was very disappointed, especially after my flight was delayed by 45 minutes on top of it."
Cons: "The poor customer service."

Cons: "Never made it so I can't rate it"

Pros: "Everything went smoothly"

Pros: "Crew was nice"
Cons: "Flight was delayed. Food was terrible"

Pros: "Large plane very comfortable"
Cons: "Nothing"

Pros: "Nice service, friendly crew."

Pros: "Kind staff and crew."
Cons: "As usual, there were extensive delays. This time it was due to a plane change initially because there was a maintenance issue. Then, we had to walk across the airport to board our other plane at a gate on the other side. Then we had to wait for the crew to arrive before we could board. It wasn't until we finally were able to board that they discovered a maintenance issue on the second plane, so we sat on the tarmac in stifling heat due to the engine not being on for an hour and a half while they worked on the plane. We didn't take off until about 11:40 central time and arrive home until 1:30 AM eastern time instead of the scheduled 11:38 PM arrival time."

Pros: "Staff was great"
Cons: "Second delay in a row"

Pros: "Pilot/Crew Communication was frequent and accurate"
Cons: "Flight was delayed 1.5 hrs due to an electronic problem after we left the gate."

Cons: "Delays both ways"

Pros: "On Time, polite smiling crew, happy passengers, overall excellent."

Pros: "Totally on time: excellent everything. This was a smooth flight both ways."

Pros: "Flight wasn't full"
Cons: "Flight was delayed an hour due to maintenance repairs."

Cons: "There should be some free tv"

Pros: "Crew was able to switch my seat so I was able to board early and have a seat where I could stretch my bad foot."
Cons: "On takeoff and landing it sounded like the plane was falling apart - literally. My confidence was shaken when it sounded like someone was sawing the belly of the plane. Very scary."

Pros: "Everything!"

Cons: "Many hours of delays from and to.."

Cons: "Had an extended overlay because of an overlap booking with our pilot. He was on another plane that wasn't due to come in until two hours later."

Pros: "Smoothly and on time"

Pros: "Willingness to check carry ons for sold out flights"
Cons: "Choosing of seats process. My traveling partner and I did not get to sit together on way home. Everyone was nice and got a free upgrade but would have been nice to sit together"

Pros: "My mother is disabled and was assigned wheelchair assistance and does not speak English very very hopeful does not have a cell phone because she is disable and does not know how to use a cell phone I was calling the one 800 number for united airlines they gave me a phone number for the terminal where she was delayed and I was just trying to check to see if my mother was aware of what was going on with the delay I just need to know if my mother was OK to give her comfort but unfortunately the number they gave me was not working I was calling over 30 rings with nobody answering for over three hours O'Hare airport was very hopeless for united airlines it's a shame that that is their head quarters i'm pretty sure I will never ever use United Airline again in my life after the terrifying experience I had waiting over four hours from my mother besides the four hour flight I was very terrified until my mother was in my arms I never ever want to experience that again or I hopefully nobody ever that uses your United airline will ever experience that"
Cons: "My mother is disabled and was assigned wheelchair assistance and does not speak English very very hopeful does not have a cell phone because she is disable and does not know how to use a cell phone I was calling the one 800 number for united airlines they gave me a phone number for the terminal where she was delayed and I was just trying to check to see if my mother was aware of what was going on with the delay I just need to know if my mother was OK to give her comfort but unfortunately the number they gave me was not working I was calling over 30 rings with nobody answering for over three hours O'Hare airport was very hopeless for united airlines it's a shame that that is their head quarters i'm pretty sure I will never ever use United Airline again in my life after the terrifying experience I had waiting over four hours from my mother besides the four hour flight I was very terrified until my mother was in my arms I never ever want to experience that again or I hopefully nobody ever that uses your United airline will ever experience that"

Pros: "Good customer service"

Read more about JetBlue
COVID-19 information

Safety measures for airlines flying from Chicago to Key West

Airlines flying from Chicago to Key West have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago to Key West

Mandatory masks

Masks required on board, masks provided on flights from Chicago to Key West

Social distancing seating

Middle seats unavailable to book on flights from Chicago to Key West

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago to Key West

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