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

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Looking for a cheap flight? 25% of our users found flights on this route for $389 or less.

FAQs for Booking Key West to Chicago Midway Flights

How long does a flight from Key West to Chicago Midway take?
An average nonstop flight takes 5h 34m, covering a distance of 1239 miles.
Which airlines provide the cheapest flights from Key West to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($563)
Do I need a passport to fly between Key West and Chicago Midway?
No.
What’s the cheapest day of the week to fly Key West to Chicago Midway?
For Key West to Chicago Midway, Wednesday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Chicago Midway back to Key West, the best deals are generally found on Sunday, with Monday being the most expensive.

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

Airports
Origin
Key West
$563
only
$563
Destination
Chicago
$563
only
$563
Wed, Apr 4
EYW
MDW
5h 55m
Wed, Apr 11
MDW
EYW
9h 09m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
LAX
Good 7.0

I received a message flight would be early but it was actually late...luckily it did not affect my connection

ATL
VPS
Good 7.3

Boarding was quick and so was the flight. No entertainment or food on short flights, that should be a N/A

MSP
ATL
Excellent 9.6

Entertainment is so appreciated on long flights. It was quiet. Snacks done quickly. Took a long time to board, but the flight was full. We were delayed out of gate because of this. Unloading plane went fairly quick but could have been a problem for short connections. Those people should have been allowed to leave first.

CUN
LAX
Okay 5.0

I loved that I was able to get home! The crew was nice.

It was very very warm in the plane. The entertainment unit was lacking.

ATL
LAX
Good 7.6

The plane was dirty. The grounds staff was complaining as we got on about having to work late.

Wed, Jul 11
EYW
MDW
6h 05m
Tue, Jul 17
MDW
EYW
5h 33m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
BDL
Excellent 10.0

Flight was on time.

Did not appreciate Aeromexico/Delta changing my flight times after I booked, giving me a more than 7 hour layover.

CUN
LAX
Okay 5.0

I loved that I was able to get home! The crew was nice.

It was very very warm in the plane. The entertainment unit was lacking.

BDL
CUN
Excellent 9.6

The plane was new and very comfortable. Free entertainment and plug for charging electronics. Love this airline!

JFK
RSW
Excellent 9.3

on time, good service,

i agreed to check in my bag at the gate when they asked for volunteers thinking I would get it at the gate of my destination but after i checked it in in gate attendant informed me that i would get my bag at the baggage claim

MSP
ATL
Excellent 9.6

Entertainment is so appreciated on long flights. It was quiet. Snacks done quickly. Took a long time to board, but the flight was full. We were delayed out of gate because of this. Unloading plane went fairly quick but could have been a problem for short connections. Those people should have been allowed to leave first.

Wed, Jul 18
EYW
MDW
6h 05m
Tue, Jul 24
MDW
EYW
5h 33m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
LAX
Good 7.0

I received a message flight would be early but it was actually late...luckily it did not affect my connection

ATL
LAX
Good 7.6

The plane was dirty. The grounds staff was complaining as we got on about having to work late.

JFK
LAS
Excellent 10.0

Smooth flight Courteous

On a five hours flight a two dollars sandwich wouldn’t hurt!!

RAP
MSP
Excellent 8.6

Very quick boarding process. There was no entertainment so I couldn't rate that.

There should be a N/A option if there is no entertainment available.

BDL
CUN
Excellent 9.6

The plane was new and very comfortable. Free entertainment and plug for charging electronics. Love this airline!

Wed, Jul 25
EYW
MDW
6h 05m
Tue, Jul 31
MDW
EYW
5h 33m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
VPS
Good 7.3

Boarding was quick and so was the flight. No entertainment or food on short flights, that should be a N/A

BOI
SLC
Good 7.6

The crew

The delay

ATL
LAX
Good 7.6

The plane was dirty. The grounds staff was complaining as we got on about having to work late.

RAP
MSP
Excellent 8.6

Very quick boarding process. There was no entertainment so I couldn't rate that.

There should be a N/A option if there is no entertainment available.

CUN
LAX
Okay 5.0

I loved that I was able to get home! The crew was nice.

It was very very warm in the plane. The entertainment unit was lacking.

Wed, Aug 1
EYW
MDW
5h 56m
Tue, Aug 7
MDW
EYW
6h 15m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
RSW
Excellent 9.3

on time, good service,

i agreed to check in my bag at the gate when they asked for volunteers thinking I would get it at the gate of my destination but after i checked it in in gate attendant informed me that i would get my bag at the baggage claim

CLE
ATL
Okay 4.6

Short trip

Very hot ride

BOI
SLC
Good 7.6

The crew

The delay

ATL
LAX
Good 7.6

The plane was dirty. The grounds staff was complaining as we got on about having to work late.

BDL
CUN
Excellent 9.6

The plane was new and very comfortable. Free entertainment and plug for charging electronics. Love this airline!

Sat, Mar 24
EYW
MDW
5h 34m
Tue, Apr 3
MDW
EYW
9h 09m
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
VPS
Good 7.3

Boarding was quick and so was the flight. No entertainment or food on short flights, that should be a N/A

ATL
LAX
Good 7.6

The plane was dirty. The grounds staff was complaining as we got on about having to work late.

DTW
LAX
Good 7.0

I received a message flight would be early but it was actually late...luckily it did not affect my connection

JFK
LAS
Excellent 10.0

Smooth flight Courteous

On a five hours flight a two dollars sandwich wouldn’t hurt!!

JFK
RSW
Excellent 9.3

on time, good service,

i agreed to check in my bag at the gate when they asked for volunteers thinking I would get it at the gate of my destination but after i checked it in in gate attendant informed me that i would get my bag at the baggage claim

Key West to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Key West
Flight Price $563
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.