Find Cheap 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: Wed May 17 2017 Return: Fri May 19 2017 Trip spans 3 days
Delta
Delta
MDW
10:10a
EYW
4:00p
5h 50m
1 stop
EYW
8:12a
MDW
3:45p
7h 33m
1 stop
Depart: Fri May 19 2017 Return: Tue May 23 2017 Trip spans 5 days
Delta
Delta
MDW
10:10a
EYW
4:00p
5h 50m
1 stop
EYW
8:12a
MDW
2:17p
6h 05m
1 stop
Depart: Mon May 22 2017 Return: Tue May 23 2017 Trip spans 2 days
Delta
Delta
MDW
10:10a
EYW
4:00p
5h 50m
1 stop
EYW
6:46a
MDW
2:17p
7h 31m
1 stop
Depart: Tue May 23 2017 Return: Tue May 30 2017 Trip spans 8 days
Delta
Delta
MDW
3:20a
EYW
9:30a
6h 10m
1 stop
EYW
6:46a
MDW
12:20p
5h 34m
1 stop
Depart: Thu Jun 1 2017 Return: Mon Jun 5 2017 Trip spans 5 days
Delta
Delta
MDW
10:10a
EYW
4:00p
5h 50m
1 stop
EYW
6:46a
MDW
2:17p
7h 31m
1 stop
Depart: Tue Jun 6 2017 Return: Fri Jun 9 2017 Trip spans 4 days
Delta
Delta
MDW
10:10a
EYW
4:00p
5h 50m
1 stop
EYW
1:46p
MDW
7:20p
5h 34m
1 stop
Depart: Sun Jun 11 2017 Return: Wed Jun 14 2017 Trip spans 4 days
Delta
Delta
MDW
10:10a
EYW
4:01p
5h 51m
1 stop
EYW
1:53p
MDW
8:02p
6h 09m
1 stop
Depart: Mon Jun 12 2017 Return: Tue Jun 20 2017 Trip spans 9 days
Delta
Delta
MDW
3:20a
EYW
9:22a
6h 02m
1 stop
EYW
11:02a
MDW
4:17p
5h 15m
1 stop
Depart: Wed Jun 14 2017 Return: Wed Jun 21 2017 Trip spans 8 days
Delta
Delta
MDW
2:00a
EYW
6:31a
4h 31m
1 stop
EYW
11:02a
MDW
6:03p
7h 01m
1 stop
Depart: Wed Jun 28 2017 Return: Sun Jul 2 2017 Trip spans 5 days
Delta
Delta
MDW
2:00a
EYW
9:22a
7h 22m
1 stop
EYW
3:00a
MDW
10:10a
7h 10m
1 stop
Depart: Tue Jul 4 2017 Return: Tue Jul 11 2017 Trip spans 8 days
Delta
Delta
MDW
8:00a
EYW
2:50p
6h 50m
1 stop
EYW
8:10a
MDW
3:40p
7h 30m
1 stop
Depart: Wed Jul 12 2017 Return: Wed Jul 19 2017 Trip spans 8 days
Delta
Delta
MDW
6:10a
EYW
12:16p
6h 06m
1 stop
EYW
3:00a
MDW
10:07a
7h 07m
1 stop
Depart: Sat Sep 9 2017 Return: Sat Sep 16 2017 Trip spans 8 days
Delta
Delta
MDW
11:55a
EYW
4:37p
4h 42m
1 stop
EYW
1:50p
MDW
7:51p
6h 01m
1 stop
Depart: Sat Sep 23 2017 Return: Sun Oct 1 2017 Trip spans 9 days
Delta
Delta
MDW
11:55a
EYW
4:37p
4h 42m
1 stop
EYW
10:55a
MDW
5:43p
6h 48m
1 stop
Depart: Tue Oct 3 2017 Return: Sun Oct 8 2017 Trip spans 6 days
Delta
Delta
MDW
2:00a
EYW
6:39a
4h 39m
1 stop
EYW
10:55a
MDW
3:40p
4h 45m
1 stop
Depart: Wed Oct 4 2017 Return: Sun Oct 8 2017 Trip spans 5 days
Delta
Delta
MDW
9:40a
EYW
4:40p
7h 00m
1 stop
EYW
10:55a
MDW
3:40p
4h 45m
1 stop
Depart: Sun Oct 8 2017 Return: Fri Oct 13 2017 Trip spans 6 days
Delta
Delta
MDW
2:00a
EYW
9:25a
7h 25m
1 stop
EYW
10:55a
MDW
5:43p
6h 48m
1 stop
Depart: Mon Oct 16 2017 Return: Sat Oct 21 2017 Trip spans 6 days
Delta
Delta
MDW
11:55a
EYW
4:40p
4h 45m
1 stop
EYW
10:55a
MDW
5:41p
6h 46m
1 stop
Depart: Tue Oct 17 2017 Return: Sat Oct 21 2017 Trip spans 5 days
Delta
Delta
MDW
2:00a
EYW
6:39a
4h 39m
1 stop
EYW
1:50p
MDW
7:51p
6h 01m
1 stop
Depart: Wed Oct 18 2017 Return: Sat Oct 21 2017 Trip spans 4 days
Delta
Delta
MDW
3:20a
EYW
9:25a
6h 05m
1 stop
EYW
1:50p
MDW
7:51p
6h 01m
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