Find Cheap Flights from Chicago Midway to Key West (MDW - EYW)

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Looking for a cheap flight? 25% of our users found flights on this route for $437 or less.

FAQs for Booking Chicago Midway to Key West Flights

How long does a flight from Chicago Midway to Key West take?
An average nonstop flight takes 4h 29m, covering a distance of 1239 miles.
Which airlines provide the cheapest flights from Chicago Midway to Key West?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($570)
Do I need a passport to fly between Chicago Midway and Key West?
No.

Book cheap flights from Chicago Midway to Key West (round-trip)

Airports
Origin
Chicago
$570
only
$570
Destination
Key West
$570
only
$570
Thu, May 10
MDW
EYW
5h 51m
Wed, May 16
EYW
MDW
6h 53m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ORD
ATL
Excellent 10.0

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

ATL
MEX
Excellent 10.0

In some Delta flights that I had in the past the plane was just ok, not bad, not good. But this plane ATL-MEX was great, very nice and conformable plane, it looks and feels excellent!

MSP
SMF
Good 6.3

For a 3 hour flight no onboard entertainment. Such a let down

SJD
ATL
Good 7.6

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.

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!!

ATL
SJD
Excellent 8.0

On time departure, actually got to Cabo early.

The seat in front of mine had a broken reclining lock mechanism and the passenger kept trying to switch from recline to sitting up and it wouldn't latch in the upright position, so he kept jerking the seatback up and down for the entire 4 hour flight. Also the rows were so tight, and seatbacks were so close together, that the reclining seat in front of me was 6 inches from my face.

Thu, Jun 7
MDW
EYW
5h 51m
Tue, Jun 12
EYW
MDW
10h 00m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ORD
ATL
Excellent 10.0

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

ATL
TYS
Excellent 9.5

Flight less than 2/3 full, lots of room for comfort. On time, no need to gate check carry on.

nothing, it was great.

MSP
SMF
Good 6.3

For a 3 hour flight no onboard entertainment. Such a let down

SJD
ATL
Good 7.6

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.

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!!

ATL
MEX
Excellent 10.0

In some Delta flights that I had in the past the plane was just ok, not bad, not good. But this plane ATL-MEX was great, very nice and conformable plane, it looks and feels excellent!

Tue, Mar 13
MDW
EYW
9h 08m
Wed, Mar 14
EYW
MDW
10h 06m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DTW
PVR
Excellent 8.6

Easy flight from check-in to boarding to deplaning.

Nothing really! No entertainment and nothing but almonds eaten.

JFK
CUN
Okay 4.0

The flight was delayed for 4 hours.

SJD
ATL
Good 7.6

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.

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!!

ORD
ATL
Excellent 10.0

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

ATL
MEX
Excellent 10.0

In some Delta flights that I had in the past the plane was just ok, not bad, not good. But this plane ATL-MEX was great, very nice and conformable plane, it looks and feels excellent!

Wed, Feb 7
MDW
EYW
9h 14m
Thu, Feb 15
EYW
MDW
7h 02m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
SLC
Mediocre 2.0

Nothing!

Everything

SJD
ATL
Good 7.6

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.

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!!

ORD
ATL
Excellent 10.0

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

MSP
CUN
Good 6.3

On time, pretty friendly crew

Too small a plane for that long a trip. Bathrooms were VERY small & rare.

JFK
CUN
Okay 4.0

The flight was delayed for 4 hours.

Tue, Mar 13
MDW
EYW
5h 18m
Tue, Mar 27
EYW
MDW
4h 41m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ORD
ATL
Excellent 10.0

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

ATL
SJD
Excellent 8.0

On time departure, actually got to Cabo early.

The seat in front of mine had a broken reclining lock mechanism and the passenger kept trying to switch from recline to sitting up and it wouldn't latch in the upright position, so he kept jerking the seatback up and down for the entire 4 hour flight. Also the rows were so tight, and seatbacks were so close together, that the reclining seat in front of me was 6 inches from my face.

JFK
SLC
Good 6.3

Too many turbulences !!!

MSP
CUN
Good 6.3

On time, pretty friendly crew

Too small a plane for that long a trip. Bathrooms were VERY small & rare.

DTW
PVR
Excellent 8.6

Easy flight from check-in to boarding to deplaning.

Nothing really! No entertainment and nothing but almonds eaten.

Mon, Apr 9
MDW
EYW
4h 34m
Sat, Apr 14
EYW
MDW
4h 47m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
SLC
Good 6.3

Too many turbulences !!!

ORD
ATL
Excellent 10.0

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

ATL
MEX
Excellent 10.0

In some Delta flights that I had in the past the plane was just ok, not bad, not good. But this plane ATL-MEX was great, very nice and conformable plane, it looks and feels excellent!

ATL
TYS
Excellent 9.5

Flight less than 2/3 full, lots of room for comfort. On time, no need to gate check carry on.

nothing, it was great.

ATL
SJD
Excellent 8.0

On time departure, actually got to Cabo early.

The seat in front of mine had a broken reclining lock mechanism and the passenger kept trying to switch from recline to sitting up and it wouldn't latch in the upright position, so he kept jerking the seatback up and down for the entire 4 hour flight. Also the rows were so tight, and seatbacks were so close together, that the reclining seat in front of me was 6 inches from my face.

Wed, Apr 18
MDW
EYW
4h 34m
Mon, Apr 23
EYW
MDW
4h 47m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
CUN
Good 6.3

On time, pretty friendly crew

Too small a plane for that long a trip. Bathrooms were VERY small & rare.

JFK
SLC
Good 6.3

Too many turbulences !!!

ATL
TYS
Excellent 9.5

Flight less than 2/3 full, lots of room for comfort. On time, no need to gate check carry on.

nothing, it was great.

MSP
SMF
Good 6.3

For a 3 hour flight no onboard entertainment. Such a let down

DEN
SLC
Mediocre 2.0

Nothing!

Everything

Sun, May 6
MDW
EYW
6h 43m
Thu, May 10
EYW
MDW
6h 41m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
SLC
Mediocre 2.0

Nothing!

Everything

ATL
SJD
Excellent 8.0

On time departure, actually got to Cabo early.

The seat in front of mine had a broken reclining lock mechanism and the passenger kept trying to switch from recline to sitting up and it wouldn't latch in the upright position, so he kept jerking the seatback up and down for the entire 4 hour flight. Also the rows were so tight, and seatbacks were so close together, that the reclining seat in front of me was 6 inches from my face.

SJD
ATL
Good 7.6

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.

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!!

ORD
ATL
Excellent 10.0

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

ATL
TYS
Excellent 9.5

Flight less than 2/3 full, lots of room for comfort. On time, no need to gate check carry on.

nothing, it was great.

Tue, Jun 5
MDW
EYW
6h 43m
Wed, Jun 13
EYW
MDW
6h 05m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
CUN
Good 6.3

On time, pretty friendly crew

Too small a plane for that long a trip. Bathrooms were VERY small & rare.

DTW
PVR
Excellent 8.6

Easy flight from check-in to boarding to deplaning.

Nothing really! No entertainment and nothing but almonds eaten.

ORD
ATL
Excellent 10.0

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

SJD
ATL
Good 7.6

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.

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!!

ATL
TYS
Excellent 9.5

Flight less than 2/3 full, lots of room for comfort. On time, no need to gate check carry on.

nothing, it was great.

Sat, Jul 14
MDW
EYW
6h 15m
Sat, Jul 21
EYW
MDW
6h 43m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
TYS
ATL
Excellent 8.4

Everything went well...on time, quick boarding and free gate check of bag.

ORD
ATL
Excellent 10.0

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

ATL
TYS
Excellent 9.5

Flight less than 2/3 full, lots of room for comfort. On time, no need to gate check carry on.

nothing, it was great.

MSP
SMF
Good 6.3

For a 3 hour flight no onboard entertainment. Such a let down

MSP
CUN
Good 6.3

On time, pretty friendly crew

Too small a plane for that long a trip. Bathrooms were VERY small & rare.

Thu, Jan 25
MDW
EYW
6h 00m
Mon, Jan 29
EYW
MDW
4h 44m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
TYS
Excellent 9.5

Flight less than 2/3 full, lots of room for comfort. On time, no need to gate check carry on.

nothing, it was great.

JFK
SLC
Good 6.3

Too many turbulences !!!

JFK
CUN
Okay 4.0

The flight was delayed for 4 hours.

SJD
ATL
Good 7.6

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.

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!!

ATL
MEX
Excellent 10.0

In some Delta flights that I had in the past the plane was just ok, not bad, not good. But this plane ATL-MEX was great, very nice and conformable plane, it looks and feels excellent!

Fri, Jan 26
MDW
EYW
4h 29m
Wed, Jan 31
EYW
MDW
4h 44m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
SLC
Mediocre 2.0

Nothing!

Everything

SJD
ATL
Good 7.6

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.

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!!

ORD
ATL
Excellent 10.0

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

JFK
SLC
Good 6.3

Too many turbulences !!!

MSP
SMF
Good 6.3

For a 3 hour flight no onboard entertainment. Such a let down

Fri, Jan 26
MDW
EYW
4h 29m
Sun, Jan 28
EYW
MDW
6h 14m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
CUN
Okay 4.0

The flight was delayed for 4 hours.

MSP
SMF
Good 6.3

For a 3 hour flight no onboard entertainment. Such a let down

DEN
SLC
Mediocre 2.0

Nothing!

Everything

SJD
ATL
Good 7.6

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.

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!!

ATL
TYS
Excellent 9.5

Flight less than 2/3 full, lots of room for comfort. On time, no need to gate check carry on.

nothing, it was great.

Chicago Midway to Key West Flight Information

Flights Arrive in Key West
Flights Depart from Chicago Midway
Flight Price $570
Distance 1239 miles
Airlines Delta
*
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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.