MDW - EYW

Find cheap flights from Chicago Midway Airport to Key West

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MDW — EYW
Nov 24 — Dec 11
Round-trip
1 adult
Economy
0 bags
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Thu 11/24
Thu 12/1

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Good to know

Low season

May

High season

November

Cheapest flight

$94

Average price round-trip

$552

Good deal round-trip

$340

Good deal one-way

$316
Best time to beat the crowds with an average 50% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Chicago Midway to Key West
(avg. price over the last 2 weeks)
or less
or less

When to book flights from Chicago Midway 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 MDW to Key West

  • Looking for a cheap flight? 25% of our users found flights on this route for $316 or less one-way and $340 or less round-trip.
  • High season is considered to be October, November and December. The cheapest month to fly is May.
  • Morning departure is around 13% 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 Midway Airport to Key West flights

Top airlines flying Chicago Midway to Key West

Scores according to KAYAK customer reviews
7.9
DeltaOverall score based on 31803 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.5Food
Airline reviews

Food was a bit mediocre, however crew was were very nice and seating was decent. Flight was delayed an hour and baggage was delayed about 45 minutes on arrival in Rome.

Read more about Delta

Food was a bit mediocre, however crew was were very nice and seating was decent. Flight was delayed an hour and baggage was delayed about 45 minutes on arrival in Rome.

Heathrow transfer from terminal to terminal is horrible packing people and suitcases into City bus with seating instead of standing room only extremely poor. Then bus driver saying push in further when we’re jammed.

All was well on this flight.

All staff very friendly and accommodating

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

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"

Plane supposed to leave FLL to TYS at 530p. There was 2nd flight scheduled for 830p. Flight 973 delayed until 9p. No explanations given. Flight did not start boarding until 920p. We didn't leave FLL until 10p. The other flight, the one at 830p was on time and arrived on time. I want an explanation for why flight 973 was delayed and why the delay was delayed from 920 to 10p before leaving FLL. I was at the airport waiting for my flight for over 8hrs. My flight was delayed 4-1/2 hrs, 530-10p. I want an explanation and I want some sort of compensation for such poor service. I didn't arrive in Knoxville until after MIDNIGHT Sun Aug 31st. I had to arrange for transportation home from the airport as my flight was delayed and delayed again and they had no idea when I would actually arrive. Isn't it a law that requires a passenger be compensated if their flight is >4 hours delayed? Allegiant apparently thinks they have no responsibility to give any reasons for their flight delays. We're just supposed to take it and like it. I requested seat on 830p flight and was told there were no available seats. Allegiant personnel was zero help from check in to crew on plane and again on ground in Knoxville. Useless is the word I would use.

Great staff, easy boarding and deplaning.

One flight attendant was rude to several customers. She was much older than the other three. They were great. I’m a senior citizen so this is not a knock on old people. Not a smile the entire flight. She even chastised a fellow flight attendant. She should not be working in the public eye and representing Allegiant Air

The check-in process couldn't have been worse. Besides they have no customer service to speak of, I wasn't able to purchase a 2nd checked bag prior to the trip, the app just wouldn't let me no matter what. I spent over an hour on hold waiting for a rep who wasn't able to help me. At the airport we politely asked the rep to help since we were unable. She flatly refused to do anything. When we asked to speak to a supervisor she said she was one of the most senior people there and if "We're still not happy she can give me a number to call where I can wait on hold for over 2 hours to be told the same thing I'm telling you now." Absolutely atrocious. First and definitely LAST time flying Allegiant.

Cons: "Not the Airline’s fault but the uber for my mom was directed to the national side of the airport which isn’t where the Allegiant terminal is (internacional wing)"
Pros: "This was my first time flying out of South Bend and I loved the smallness of the airport and the option to take a direct flight to Vegas to cost family. No long lines and crowds made it easy to social distance."
Cons: "I would have liked it the seat reclined slightly or had the adjustable headrest so my head wouldn't flop back and forth while I took a nap."
Pros: "Great crew."
Cons: "Nothing"
Pros: "The passengers were spaced out, so we could actually social distance."
Cons: "Not all passengers wore masks. During a contagious pandemic. What the actual hell? Also, the tray tables are too small to use for anything, and we didn’t even get a free drink. Water and soda are so cheap, it’s absurd. I’d never take Allegiant again if they weren’t basically the only airline operating out of my town’s small airport."
Cons: "No help with the Coronavirus bs. Customer service blows"
Pros: "Quick flight, arrived ahead of schedule"
Cons: "The smell"
Cons: "A plan to deal with a hostile mom with a screaming kid that was out of control."
Pros: "Florida was amazing. The people were very friendly."
Cons: "Nothing"
Pros: "Friendly crew."
Cons: "Built in headrests on the seats."
Pros: "Nothing"
Cons: "Everything"
Pros: "The crew was the best on any flight I have been on. Love their jokes."
Pros: "The crew was good , plane was delayed and late for departure. Second flight was delayed by 2 1/2 hours , I just can’t catch a break !!"
Cons: "I could not log onto the website and check my carryon bag , cost me $50 at check in. It would not recognize my number for the first flight. I’m a known traveler on Frontier so I did log in with them ."
Pros: "Pilot was friendly"
Cons: "A little confusion about departure gate"
Pros: "Great flight"
Pros: "The staff were friendly and helpful and boarded us in an orderly manner."
Cons: "Staff are part time employees and do not arrive to check in counter until 1.5 hours before flight. When flying out of this airport you do not need to arrive 2 hours early."
Pros: "Short flight and pilot was able to explain delay"
Cons: "Long delay due to many planes in front of us, no offer of water only drinks we have to pay for"
Pros: "It was great"
Pros: "The flight attendants, the space on the plane, the prompt departure and arrival!"
Cons: "Media has not been reflective of my great experience."
Cons: "Lousy airline. Left gate late and unfriendly crew. Wanted to charge me for carry on."
Pros: "Direct flight in less than 3 hours"
Pros: "Flight attendants were nice."
Cons: "There was no one working at the counter when we arrived at the airport and there was already a sizable line. We waited about 10 minutes before anyone showed up to assist customers. Not sure what was up with that. Very uncomfortable seats and crowded seating on plane which is typical these days everything else went fine. Flight left and arrived on time."
Pros: "On time"
Cons: "initially assigned to center seat."
Pros: "Friendly staff!!"
Cons: "Hour delay on flight"
Pros: "Price"
Pros: "Affordable and fast"
Cons: "Big guy sitting next to me took up 2 seats!!"
Pros: "It got us there and back for a descent price. The flight was fine but the seats are not comfortable and do not recline. I wouldn't suggest Allegiant for anything more than 2 hours and that was even pushing it."
Cons: "We arrived 3.5 hours early and the line was very long. They must have had a system glitch but didn't communicate to anyone in the line as to what was going on. When it did come time to board, they told everyone in the line that was going to Cincinnati that we couldn't check in until 2 hours before the departure time. Apparently there were some other flights that left before us. If they had told us to keep our place in line and to let other people through, that wouldn't have been a problem. But, they didn't. Their own website says you should check baggage at least 2 hours before your flight and no more than 4 hours before. They took it upon themselves to change the rules on people who arrive early. Then, once they no longer had anyone else to check in, they changed their rules again and start checking in people for Cincinnati about 2.5 hours ahead of time. A little communication and brain power from the staff would have gone a long way. After all that mess, the flight was delayed leaving about 15 minutes without any updates from Allegiant either."
Pros: "From entering the airport, gate, and plane- nothing is more pleasant and efficient than Allegiant flights. I was able to attend my grandsons bday and back by start of the next week- round trip at REASONBLE prices! Thank you."
Cons: "I am ok with it but the walk way was so filthy on my return trip. I know plane was late and we boarded late... but a really quick vacuum would have taken only a few minutes. I realize it was messy from cl"
Pros: "Price!"
Cons: "First flight being cancelled"
Pros: "Boarding at the new Austin South terminal was a breeze!"
Cons: "It's ridiculous to make passengers keep their personal items on the floor when most of the overhead lockers are empty. Ridiculous and dangerous."
Pros: "Great price. Direct route. Friendly gate staff and flight crew. On time (actually early) departure and arrival."
Cons: "Flip side of departing early is they closed boarding over 30 minutes before scheduled departure (nearly missed flight)."
Pros: "friendly staff and clean enviornment. no nonsense flight."
Cons: "nothing to say except that seats could be a little more comfortable."
Cons: "Allegiant 468 7/27 4 1/2 hour delay on flight 569 on 7/27 and not a single person on the ground or plane even said sorry. Allegiant also failed to update the revised departure time. Allegiant posted an initial delay of 30 minunutes but then, when there was a further 2 hour delay due to a problem with the plane in Vegas Allegiant didn't update the time. (G4 568 was showing a two hour delay, with a 1010 arrival into STS but Allegiant never updated the departure time for 569 to reflect the additional two hour delay.) It wasn't until I called that it got updated and when I called I had to point out that the airplane hadn't even left Vegas and Allegiant was still showing an 8:50 departure time. It also took the reservation agent over 20 minutes to get any information about what was going on. Lastly each and every time I call I was on hold for a minimum of 20 minutes before being able to speak to a person"
Pros: "More room in seats. Low prices Nice staff."
Cons: "NO DRINKS!! not even water is complementary!! NO SNACKS!! Not even pretzels!! WOW! You have to pay for your carry ons. You have to pay for your checked bag ($50!) You are only allowed 40# in your checked in without an additional fee."
Pros: "While I enjoy the fact that Allegiant offers direct flights to Laredo at an affordable price, the planes really need to be updated."
Cons: "We really disliked that we boarded the plane and just before taking off they made us get off again and never did confirm the real reason. The planes really need better maintenance since this is the second time in two weeks we have to change planes due to problems."
Cons: "First they delayed the flight and then they cancelled the day of and I had to book a whole new flight for the day which was costly. I will never recommend that airline to anyone and I wanted to like it since I looked at their website and it looked very military friendly, but it was just disappointing"
Pros: "Nothing"
Cons: "I paid for 1A. Was moved because "the crew needed the seat" to the middle. There were SO many open seats. Was unacceptable."
Pros: "The crew and pilot"
Cons: "Entertainment."
Pros: "The prices are good. Anything additional (food, overhead carry on space) is an additional cost but this is how they make the tickets cheaper for people who don't need extras."
Pros: "The crew was awesome! They were friendly and very focused on their passengers. The plane was clean and the flight, itself was great. Worth flying from Oregon to So. Cal., will do again. Loved the flight times, and because of them, we were able to have half a day on departure day (Thursday 3:30 pm) to drop off dogs, pack and run errands and some work and arriving back home (Tuesday 9:46 am) gave us all day to work and get ready for the week."
Cons: "Plane did not board or leave on time, spent a lot of time waiting both on and off plane. I also did not like being hit with the taxes and fees at Alamo, after booking through Allegiant. Those should have been included in the initial payment, because I could have rented same vehicle for $40 less through Alamo website,(final payment w/ T&F's) That was a waste of your customer's money."
Cons: "The flight from Las Vegas was changed twice"
Cons: "I moved my seat when I checked in to sit with a friend and paid about ten bucks for a different seat. I didn't think much of it until I got to my new seat and realized I had paid to sit in a seat that was basically a bench that didn't recline and was right in front of the bathroom so it rattled every time someone flushed. Classy."
Pros: "Fast seating with veteran's seated first."
Cons: "Small seats that don't recline."
Pros: "Nothing"
Cons: "Flight was canceled but they keep telling us that in an hour and that hour never came. We are stuck at the airport. We should get upgraded to 1st class"
Cons: "That you guys so tight that would not even offer free water....."

Book cheap flights from Chicago Midway Airport to Key West

Recent round-trip flight deals

1/15Sun
1 stopMultiple Airlines
24h 45mMDW-EYW
1/28Sat
1 stopMultiple Airlines
8h 43mEYW-MDW
$237
12/20Tue
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$256
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$260
2/24Fri
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$264
12/21Wed
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6h 05mMDW-EYW
12/28Wed
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5h 48mEYW-MDW
$266
2/23Thu
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$271
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$272
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$273
12/5Mon
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4/19Wed
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2/20Mon
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12/13Tue
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4h 32mMDW-EYW
12/20Tue
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6h 55mEYW-MDW
$322

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Chicago Midway Airport - Key West Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Key West (EYW)United States

Return flight deals:

Key West - Chicago Midway Airport

Cabin classes:

$1,111
$340

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