Find cheap flights from Chicago Midway Airport to Key West

MDW - EYW

Find cheap flights from Chicago Midway Airport to Key West

Round-trip
Economy
Chicago (MDW)
Key West
Tue 12/1
Tue 12/8
Any month
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Good to know

Low season

May Best time to beat the crowds with an average 21% drop in price.

High season

April Most popular time to fly with an average 38% increase in price.

Average price round-trip

$516 (avg. price over the last 2 weeks)

Good deal round-trip

$452 or less

When to book flights from Chicago Midway to Key West

Estimated round-trip price
Average price per month

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $452 or less round-trip.
  • High season is considered to be March, April and May. The cheapest month to fly is May.
  • Morning departure is around 9% 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

Are there Key West travel restrictions currently due to Coronavirus?

How long does a flight from Chicago Midway Airport to Key West take?

Which airlines provide the cheapest flights from Chicago Midway Airport to Key West?

Do I need a passport to fly between Chicago Midway Airport and Key West?

How does KAYAK find such low prices on flights from Chicago Midway Airport to Key West?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Key West?

What is the Hacker Fare option on flights from Chicago Midway Airport to Key West?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Key West?

Top airline flying Chicago Midway to Key West

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,799 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Cons: "Seats were a little dirty especially for the COVID-19 going around."

Pros: "The atl to bwi leg was not great. No inflight entertainment and the aircraft looked old."
Cons: "A newer aircraft that doesn't show its age would be nice"

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

Cons: "It was FREEZING throughout the entire flight. Freezing. No blankets. Missed having screen in seat but was able to start a movie on my phone so it was fine."

Pros: "I fly a lot, and I am very impressed with the level of consistency that Delta has offered the last couple of months. This flight didn’t disappoint. The crew was particularly friendly"
Cons: "Nothing I can think of-10/10"

Pros: "Great and faster"

Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."

Pros: "The crew was great and also the snacks."

Pros: "The seat was very comfortable even as a basic seating and the entertainment options were great."
Cons: "The voice from the pilot was very loud and would be too much if I had my headphones on."

Cons: "Too much delay - departure was planned on March 15 @ 7 pm and take off happened on March 16 @ 12pm - a complete failure!!!!"

Pros: "It was ok"
Cons: "They lost my suitcase. Now I have to wait a day or two and they won’t sent it to me."

Pros: "Early and middle seat was open!"
Cons: "Coffee tasted like fish. :("

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: "Comfort"
Cons: "WiFi never connects food"

Cons: "Security in PRG was little bit strong They ask my about my last job - 15 years ago if I did not fight with my Manager(I forgat his name)"

Pros: "The crew both going and coming from San Jose, Costa Rica were incredible."
Cons: "The long waits on the tarmac waiting on other planes to leave. Which was a big problem because it caused a lot of us to either barely miss our flight or miss our flight."

Cons: "The attitude of the employees."

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: "Great airline stewards"
Cons: "Suggestion- Overhead bin should be assigned to the seat the person is seated in."

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: "The flight was a Christmas gift for my mother to spend some time with her friends in Mazatlán. I heard she spent the entire day waiting at the airport as her flight was rescheduled 4 times."

Cons: "Sat by the exit seat so the door was a bit more chilly. No food. Small entertainment screens with audio bleed through."

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

Pros: "The movies were spectacular"
Cons: "Food was a bit plain"

Cons: "There was no gluten free snack option."

Pros: "I always enjoy my flights on Delta the staff members are always pleasant and helpful, not to mention a smooth flight. :)"

Pros: "On time flight"
Cons: "Cramped seating in coach. Think comfort not profit"

Cons: "Condition of the airplane"

Pros: "It was quick and on time relatively smooth flights with little turbulance."
Cons: "Economy seats are too small you literally can't move your elbow without hitting the person next to you. And there was no point at which we weren't all touching legs."

Pros: "The crew had the most amazing attitude. Very friendly. It really makes a big difference. Seemed like the positive attitude was contagious. Thanks to them."
Cons: "The seats were entirely too close. Not enough legroom. Legroom was easily two inches less than typical. I am 6'4" and I could not get my knees to go behind the seat in front of me. I had one knee in the aisle and the other between the two seats in front of me. I know I'm taller than average, but I don't think I'm asking too much. Just want to be able to sit normally."

Pros: "the flight was on time and the staff very helpful"

Pros: "Food, crew, boarding"
Cons: "I had a screen in front of me that did not work. It was annoying. Fix it."

Pros: "I got a seat in the exit row with lots of leg room. The entertainment that I didn't use offered a great selection with very recent movies, etc."
Cons: "I didn't like that I had to take a bus to my terminal. I didn't like the fact that my gate was changed more than five times. I didn't like that my flight time was changed more than 15 times with no reason why until boarding time. I didn't like the fact that I did not get a seat assignment until boarding the plane. I didn't like the fact that they couldn't manage to scramble another plane and crew, but instead forced us to wait over four hours for one that was stuck somewhere else in the country."

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: "Your flight attendants were very personable and made a very long flight a comfortable as it could possibly be. They were pleasant and always available. Delta is always my go to airline ... especially on long trips as I upgraded to economy comfort and had a few more inches of leg room!"

Cons: "I purchased my tickets about 5 weeks before my trip and got to the airport 2 hrs prior. I recieved no seat assignment, just a boarding pass that said request seat. So I requested a seat. Then the people were rude and told me to come back, so I did about 45 min later and asked again, they were rude again and said come back later. The third time I got s seat assigned but again, they were very rude. Won't fly delta again."

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."

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: "On time"

Cons: "I booked with Delta who doesnt give you limits of weight for the carryon...why since the flight was operated from Airfrance they gave me limits of weight of 12 kg??? one ticket one law pls again, the hostess in my row was very nice, even the steward who was working with her very snob...it's not his job"

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: "My baggage did not arrive. The representative at the airport told me they would call me last night when my bag came in, but no one ever called. I saw online that the flight my bag was on was cancelled. I have not been able to reach anyone about the status of my bag this morning. I'm staying 30 miles from the airport and will have to drive back to get my bag (if it ever arrives)."

Pros: "The flight attendant was friendly and funny!"

Cons: "I have a 10 month old infant and I sat next to the motor. I didn't have a chance to move my seat so the poor people next to me had to deal with a screaming infant the whole time. I wish I would have at least had the chance to upgrade but it never gave me and option to pick a seat. I was very unhappy about that."

Pros: "Pleasant boarding. Delta gate at MSP is very comfortable."
Cons: "Usual cramped seats, $25 charge for luggage, cheap snacks."

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Chicago Midway to Key West

Airlines flying from Chicago Midway 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 Midway to Key West

Mandatory masks

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

Social distancing seating

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

Pre-flight testing

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

Book cheap flights from Chicago Midway Airport to Key West

Recent round-trip flight deals

2/10
Wed
1 stop
Delta
8h 34m
MDW - EYW
2/14
Sun
1 stop
Delta
6h 18m
EYW - MDW
12/18
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1 stop
Delta
8h 35m
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12/24
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1 stop
Delta
9h 50m
EYW - MDW
12/21
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1 stop
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8h 35m
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12/25
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1 stop
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9h 50m
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5/29
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9h 51m
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6/5
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7h 40m
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1/10
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6h 58m
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1/16
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4h 43m
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12/16
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7h 35m
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12/23
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9h 55m
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1/3
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4h 35m
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1/10
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7h 46m
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27h 09m
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12/19
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15h 34m
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4/6
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2 stops
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9h 24m
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4/10
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6h 15m
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11h 52m
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2/14
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6h 58m
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2/17
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4h 43m
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1/15
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7h 16m
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1/19
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1 stop
Delta
6h 08m
EYW - MDW
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Recent one-way flight deals

12/23
Wed
1 stop
Delta
4h 25m
MDW - EYW
12/29
Tue
1 stop
Delta
7h 16m
MDW - EYW
12/12
Sat
1 stop
Delta
7h 35m
MDW - EYW
12/28
Mon
1 stop
Delta
7h 16m
MDW - EYW
12/7
Mon
1 stop
Delta
7h 35m
MDW - EYW
12/19
Sat
1 stop
Delta
7h 16m
MDW - EYW
1/21
Thu
1 stop
Delta
7h 16m
MDW - EYW
12/5
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1 stop
Delta
7h 35m
MDW - EYW
12/27
Sun
1 stop
Delta
6h 55m
MDW - EYW
12/5
Sat
3 stops
Multiple Airlines
22h 21m
MDW - EYW
12/5
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3 stops
Multiple Airlines
22h 21m
MDW - EYW
12/12
Sat
3 stops
Multiple Airlines
22h 21m
MDW - EYW
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