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

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
Students
under 26
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago Midway to Key West

(Round-trip)
Depart: Thu Dec 22 2016 Return: Mon Dec 26 2016 Trip spans 5 days
Delta
Delta
MDW
5:51a
EYW
10:52a
5h 01m
1 stop
EYW
5:50a
MDW
1:22p
7h 32m
1 stop
Depart: Sun Jan 1 2017 Return: Thu Jan 5 2017 Trip spans 5 days
Delta
Delta
MDW
7:20a
EYW
12:49p
5h 29m
1 stop
EYW
11:19a
MDW
6:21p
7h 02m
1 stop
Depart: Thu Jan 5 2017 Return: Tue Jan 10 2017 Trip spans 6 days
Delta
Delta
MDW
5:51a
EYW
10:51a
5h 00m
1 stop
EYW
5:49a
MDW
11:03a
5h 14m
1 stop
Depart: Fri Jan 6 2017 Return: Tue Jan 10 2017 Trip spans 5 days
Delta
Delta
MDW
5:51a
EYW
10:51a
5h 00m
1 stop
EYW
5:49a
MDW
11:03a
5h 14m
1 stop
Depart: Wed Jan 11 2017 Return: Tue Jan 17 2017 Trip spans 7 days
Delta
Delta
MDW
5:30a
EYW
10:54a
5h 24m
1 stop
EYW
9:53a
MDW
4:02p
6h 09m
1 stop
Depart: Sat Jan 14 2017 Return: Tue Jan 17 2017 Trip spans 4 days
Delta
Delta
MDW
8:45a
EYW
3:03p
6h 18m
1 stop
EYW
8:35a
MDW
4:02p
7h 27m
1 stop
Depart: Fri Jan 20 2017 Return: Mon Jan 23 2017 Trip spans 4 days
Delta
Delta
MDW
1:00a
EYW
6:55a
5h 55m
1 stop
EYW
12:35p
MDW
6:46p
6h 11m
1 stop
Depart: Sat Jan 21 2017 Return: Sat Jan 28 2017 Trip spans 8 days
Delta
Delta
MDW
2:10a
EYW
6:53a
4h 43m
1 stop
EYW
12:35p
MDW
6:07p
5h 32m
1 stop
Depart: Fri Feb 3 2017 Return: Sun Feb 5 2017 Trip spans 3 days
Delta
Delta
MDW
9:08a
EYW
3:04p
5h 56m
1 stop
EYW
8:35a
MDW
1:19p
4h 44m
1 stop
Depart: Sun Feb 5 2017 Return: Fri Feb 10 2017 Trip spans 6 days
Delta
Delta
MDW
2:10a
EYW
6:53a
4h 43m
1 stop
EYW
8:35a
MDW
1:22p
4h 47m
1 stop
Depart: Mon Feb 6 2017 Return: Fri Feb 10 2017 Trip spans 5 days
Delta
Delta
MDW
2:10a
EYW
6:55a
4h 45m
1 stop
EYW
7:11a
MDW
1:22p
6h 11m
1 stop
Depart: Tue Feb 7 2017 Return: Fri Feb 10 2017 Trip spans 4 days
Delta
Delta
MDW
1:00a
EYW
5:31a
4h 31m
1 stop
EYW
2:00a
MDW
7:45a
5h 45m
1 stop
Depart: Wed Feb 8 2017 Return: Fri Feb 10 2017 Trip spans 3 days
Delta
Delta
MDW
2:10a
EYW
6:55a
4h 45m
1 stop
EYW
7:11a
MDW
1:22p
6h 11m
1 stop
Depart: Fri Feb 10 2017 Return: Mon Feb 13 2017 Trip spans 4 days
Delta
Delta
MDW
7:20a
EYW
3:04p
7h 44m
1 stop
EYW
12:35p
MDW
6:46p
6h 11m
1 stop
Depart: Sat Feb 11 2017 Return: Mon Feb 13 2017 Trip spans 3 days
Delta
Delta
MDW
5:30a
EYW
10:52a
5h 22m
1 stop
EYW
12:35p
MDW
6:46p
6h 11m
1 stop
Depart: Fri Feb 24 2017 Return: Wed Mar 1 2017 Trip spans 6 days
Delta
Delta
MDW
10:30a
EYW
3:02p
4h 32m
1 stop
EYW
2:00a
MDW
7:47a
5h 47m
1 stop
Depart: Thu Mar 9 2017 Return: Thu Mar 16 2017 Trip spans 7 days
Delta
Delta
MDW
8:45a
EYW
3:05p
6h 20m
1 stop
EYW
6:45a
MDW
2:38p
7h 53m
1 stop
Depart: Sat Mar 11 2017 Return: Mon Mar 13 2017 Trip spans 2 days
Delta
Delta
MDW
10:30a
EYW
3:05p
4h 35m
1 stop
EYW
1:50p
MDW
7:07p
5h 17m
1 stop
Depart: Mon Mar 13 2017 Return: Thu Mar 16 2017 Trip spans 4 days
Delta
Delta
MDW
9:45a
EYW
4:05p
6h 20m
1 stop
EYW
9:30a
MDW
2:38p
5h 08m
1 stop
Depart: Fri Mar 17 2017 Return: Tue Mar 21 2017 Trip spans 5 days
Delta
Delta
MDW
2:00a
EYW
9:21a
7h 21m
1 stop
EYW
9:30a
MDW
2:38p
5h 08m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Chicago
$452
Destination

Key West
$452
Airlines