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: Mon Feb 6 2017 Return: Thu Feb 9 2017 Trip spans 4 days
Delta
Delta
MDW
10:40a
EYW
4:44p
6h 04m
1 stop
EYW
8:35a
MDW
4:02p
7h 27m
1 stop
Depart: Tue Feb 7 2017 Return: Fri Feb 10 2017 Trip spans 4 days
Delta
Delta
MDW
1:00a
EYW
8:13a
7h 13m
1 stop
EYW
8:35a
MDW
4:02p
7h 27m
1 stop
Depart: Fri Feb 10 2017 Return: Wed Feb 15 2017 Trip spans 6 days
Delta
Delta
MDW
1:00a
EYW
8:13a
7h 13m
1 stop
EYW
12:35p
MDW
6:46p
6h 11m
1 stop
Depart: Sun Feb 12 2017 Return: Mon Feb 13 2017 Trip spans 2 days
Delta
Delta
MDW
2:10a
EYW
8:13a
6h 03m
1 stop
EYW
2:00a
MDW
9:33a
7h 33m
1 stop
Depart: Mon Feb 13 2017 Return: Thu Feb 16 2017 Trip spans 4 days
Delta
Delta
MDW
1:00a
EYW
5:31a
4h 31m
1 stop
EYW
8:35a
MDW
1:22p
4h 47m
1 stop
Depart: Tue Feb 14 2017 Return: Thu Feb 16 2017 Trip spans 3 days
Delta
Delta
MDW
1:00a
EYW
5:31a
4h 31m
1 stop
EYW
8:35a
MDW
1:22p
4h 47m
1 stop
Depart: Wed Feb 15 2017 Return: Thu Feb 16 2017 Trip spans 2 days
Delta
Delta
MDW
5:30a
EYW
10:54a
5h 24m
1 stop
EYW
5:49a
MDW
11:03a
5h 14m
1 stop
Depart: Sun Feb 19 2017 Return: Wed Feb 22 2017 Trip spans 4 days
Delta
Delta
MDW
7:25a
EYW
3:05p
7h 40m
1 stop
EYW
7:12a
MDW
1:50p
6h 38m
1 stop
Depart: Mon Feb 20 2017 Return: Thu Feb 23 2017 Trip spans 4 days
Delta
Delta
MDW
1:00a
EYW
5:32a
4h 32m
1 stop
EYW
2:00a
MDW
7:43a
5h 43m
1 stop
Depart: Tue Feb 21 2017 Return: Fri Feb 24 2017 Trip spans 4 days
Delta
Delta
MDW
1:00a
EYW
8:24a
7h 24m
1 stop
EYW
8:36a
MDW
1:50p
5h 14m
1 stop
Depart: Wed Feb 22 2017 Return: Fri Feb 24 2017 Trip spans 3 days
Delta
Delta
MDW
5:30a
EYW
10:50a
5h 20m
1 stop
EYW
8:36a
MDW
1:50p
5h 14m
1 stop
Depart: Thu Feb 23 2017 Return: Fri Feb 24 2017 Trip spans 2 days
Delta
Delta
MDW
7:25a
EYW
3:05p
7h 40m
1 stop
EYW
8:36a
MDW
1:50p
5h 14m
1 stop
Depart: Fri Feb 24 2017 Return: Tue Feb 28 2017 Trip spans 5 days
Delta
Delta
MDW
7:25a
EYW
3:05p
7h 40m
1 stop
EYW
8:36a
MDW
1:50p
5h 14m
1 stop
Depart: Sat Feb 25 2017 Return: Tue Feb 28 2017 Trip spans 4 days
Delta
Delta
MDW
8:45a
EYW
3:04p
6h 19m
1 stop
EYW
8:36a
MDW
1:50p
5h 14m
1 stop
Depart: Sun Feb 26 2017 Return: Tue Feb 28 2017 Trip spans 3 days
Delta
Delta
MDW
7:25a
EYW
3:05p
7h 40m
1 stop
EYW
8:36a
MDW
4:27p
7h 51m
1 stop
Depart: Mon Feb 27 2017 Return: Tue Feb 28 2017 Trip spans 2 days
Delta
Delta
MDW
9:11a
EYW
3:05p
5h 54m
1 stop
EYW
8:36a
MDW
1:50p
5h 14m
1 stop
Depart: Tue Feb 28 2017 Return: Fri Mar 3 2017 Trip spans 4 days
Delta
Delta
MDW
1:00a
EYW
6:56a
5h 56m
1 stop
EYW
2:00a
MDW
7:43a
5h 43m
1 stop
Depart: Wed Mar 1 2017 Return: Sat Mar 4 2017 Trip spans 4 days
Delta
Delta
MDW
2:10a
EYW
8:24a
6h 14m
1 stop
EYW
8:36a
MDW
1:59p
5h 23m
1 stop
Depart: Sat Mar 4 2017 Return: Mon Mar 6 2017 Trip spans 3 days
Delta
Delta
MDW
2:10a
EYW
9:40a
7h 30m
1 stop
EYW
2:00a
MDW
7:43a
5h 43m
1 stop
Depart: Sun Mar 5 2017 Return: Mon Mar 6 2017 Trip spans 2 days
Delta
Delta
MDW
7:25a
EYW
3:05p
7h 40m
1 stop
EYW
2:00a
MDW
9:34a
7h 34m
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
$508
Destination

Key West
$508
Airlines