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
The price shown for each flight will be the average for all passengers including any infants.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

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 Apr 24 2017 Return: Fri Apr 28 2017 Trip spans 5 days
Delta
Delta
MDW
3:20a
EYW
7:56a
4h 36m
1 stop
EYW
1:50p
MDW
7:25p
5h 35m
1 stop
Depart: Wed Apr 26 2017 Return: Tue May 2 2017 Trip spans 7 days
Delta
Delta
MDW
10:08a
EYW
4:00p
5h 52m
1 stop
EYW
3:00a
MDW
10:33a
7h 33m
1 stop
Depart: Sun Apr 30 2017 Return: Wed May 3 2017 Trip spans 4 days
Delta
Delta
MDW
10:08a
EYW
4:00p
5h 52m
1 stop
EYW
1:46p
MDW
7:20p
5h 34m
1 stop
Depart: Tue May 9 2017 Return: Sat May 13 2017 Trip spans 5 days
Delta
Delta
MDW
2:00a
EYW
6:32a
4h 32m
1 stop
EYW
9:34a
MDW
2:15p
4h 41m
1 stop
Depart: Sat May 13 2017 Return: Wed May 17 2017 Trip spans 5 days
Delta
Delta
MDW
3:20a
EYW
9:28a
6h 08m
1 stop
EYW
6:46a
MDW
12:20p
5h 34m
1 stop
Depart: Sun May 14 2017 Return: Sat May 20 2017 Trip spans 7 days
Delta
Delta
MDW
6:21a
EYW
12:06p
5h 45m
1 stop
EYW
9:34a
MDW
4:58p
7h 24m
1 stop
Depart: Tue May 23 2017 Return: Tue May 30 2017 Trip spans 8 days
Delta
Delta
MDW
10:10a
EYW
4:00p
5h 50m
1 stop
EYW
3:00a
MDW
8:29a
5h 29m
1 stop
Depart: Wed Jun 7 2017 Return: Tue Jun 13 2017 Trip spans 7 days
Delta
Delta
MDW
6:21a
EYW
12:06p
5h 45m
1 stop
EYW
3:00a
MDW
8:20a
5h 20m
1 stop
Depart: Mon Jun 12 2017 Return: Wed Jun 14 2017 Trip spans 3 days
Delta
Delta
MDW
6:10a
EYW
12:16p
6h 06m
1 stop
EYW
8:10a
MDW
2:22p
6h 12m
1 stop
Depart: Wed Aug 16 2017 Return: Wed Aug 23 2017 Trip spans 8 days
Delta
Delta
MDW
6:10a
EYW
12:16p
6h 06m
1 stop
EYW
8:10a
MDW
2:22p
6h 12m
1 stop
Depart: Wed Aug 23 2017 Return: Sat Aug 26 2017 Trip spans 4 days
Delta
Delta
MDW
9:40a
EYW
2:50p
5h 10m
1 stop
EYW
10:55a
MDW
5:41p
6h 46m
1 stop
Depart: Fri Aug 25 2017 Return: Tue Aug 29 2017 Trip spans 5 days
Delta
Delta
MDW
6:10a
EYW
12:16p
6h 06m
1 stop
EYW
1:50p
MDW
7:48p
5h 58m
1 stop
Depart: Sun Aug 27 2017 Return: Thu Aug 31 2017 Trip spans 5 days
Delta
Delta
MDW
11:55a
EYW
4:40p
4h 45m
1 stop
EYW
10:55a
MDW
5:43p
6h 48m
1 stop
Depart: Sat Sep 9 2017 Return: Tue Sep 12 2017 Trip spans 4 days
Delta
Delta
MDW
11:55a
EYW
4:37p
4h 42m
1 stop
EYW
8:10a
MDW
3:40p
7h 30m
1 stop
Depart: Fri Sep 29 2017 Return: Mon Oct 2 2017 Trip spans 4 days
Delta
Delta
MDW
9:40a
EYW
4:40p
7h 00m
1 stop
EYW
10:55a
MDW
5:43p
6h 48m
1 stop
Depart: Thu Apr 20 2017 Return: Mon Apr 24 2017 Trip spans 5 days
Delta
Delta
MDW
10:08a
EYW
4:00p
5h 52m
1 stop
EYW
3:00a
MDW
10:33a
7h 33m
1 stop
Depart: Sat Jun 17 2017 Return: Tue Jun 20 2017 Trip spans 4 days
Delta
Delta
MDW
8:00a
EYW
2:47p
6h 47m
1 stop
EYW
3:00a
MDW
8:20a
5h 20m
1 stop
Depart: Tue Jun 20 2017 Return: Thu Jun 29 2017 Trip spans 10 days
Delta
Delta
MDW
3:20a
EYW
9:25a
6h 05m
1 stop
EYW
10:55a
MDW
5:43p
6h 48m
1 stop
Depart: Thu Jun 22 2017 Return: Tue Jun 27 2017 Trip spans 6 days
Delta
Delta
MDW
9:40a
EYW
2:50p
5h 10m
1 stop
EYW
1:50p
MDW
7:48p
5h 58m
1 stop
Depart: Thu Jul 13 2017 Return: Tue Jul 18 2017 Trip spans 6 days
Delta
Delta
MDW
9:40a
EYW
2:50p
5h 10m
1 stop
EYW
3:00a
MDW
8:20a
5h 20m
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