Find Cheap Flights from Chicago Midway to Caribbean

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.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago Midway to Caribbean

(Round-trip)
Depart: Mon Aug 14 2017 Return: Fri Aug 18 2017 Trip spans 5 days
Delta
Delta
MDW
HAV
15h 53m
1 stop
HAV
MDW
9h 18m
1 stop
Depart: Fri Sep 29 2017 Return: Sat Oct 7 2017 Trip spans 9 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
9h 30m
1 stop
Depart: Sat Aug 19 2017 Return: Sat Aug 26 2017 Trip spans 8 days
Delta
Delta
MDW
HAV
15h 21m
2 stops
HAV
MDW
9h 30m
1 stop
Depart: Wed Aug 30 2017 Return: Wed Sep 6 2017 Trip spans 8 days
Delta
Delta
MDW
HAV
17h 05m
2 stops
HAV
MDW
11h 55m
2 stops
Depart: Mon Oct 9 2017 Return: Tue Oct 17 2017 Trip spans 9 days
Delta
Delta
MDW
HAV
16h 50m
2 stops
HAV
MDW
12h 42m
2 stops
Depart: Fri Aug 25 2017 Return: Sat Sep 2 2017 Trip spans 9 days
Delta
Delta
MDW
HAV
16h 15m
1 stop
HAV
MDW
7h 06m
1 stop
Depart: Sat Oct 14 2017 Return: Wed Oct 18 2017 Trip spans 5 days
Delta
Delta
MDW
HAV
17h 20m
1 stop
HAV
MDW
9h 32m
1 stop
Depart: Mon Aug 14 2017 Return: Wed Aug 23 2017 Trip spans 10 days
Delta
Delta
MDW
STT
6h 30m
1 stop
STT
MDW
8h 08m
1 stop
Depart: Tue Sep 19 2017 Return: Tue Sep 26 2017 Trip spans 8 days
Delta
Delta
MDW
STT
6h 27m
1 stop
STT
MDW
9h 32m
1 stop
Depart: Wed Nov 22 2017 Return: Tue Nov 28 2017 Trip spans 7 days
Delta
Delta
MDW
HAV
4h 55m
1 stop
HAV
MDW
9h 13m
1 stop
Depart: Wed Nov 22 2017 Return: Tue Nov 28 2017 Trip spans 7 days
Delta
Delta
MDW
HAV
4h 55m
1 stop
HAV
MDW
9h 13m
1 stop
Depart: Wed Sep 6 2017 Return: Thu Sep 21 2017 Trip spans 16 days
Delta
Delta
MDW
SJU
6h 32m
1 stop
SJU
MDW
8h 17m
1 stop
Depart: Wed Oct 4 2017 Return: Tue Oct 10 2017 Trip spans 7 days
Delta
Delta
MDW
SJU
6h 32m
1 stop
SJU
MDW
9h 48m
1 stop
Depart: Wed Oct 18 2017 Return: Wed Oct 25 2017 Trip spans 8 days
Delta
Delta
MDW
SJU
8h 34m
1 stop
SJU
MDW
7h 12m
1 stop
Depart: Tue Jul 11 2017 Return: Thu Jul 27 2017 Trip spans 17 days
Delta
Delta
MDW
HAV
15h 53m
1 stop
HAV
MDW
9h 20m
1 stop
Depart: Tue Sep 26 2017 Return: Tue Oct 3 2017 Trip spans 8 days
Delta
Delta
MDW
SJU
8h 34m
1 stop
SJU
MDW
8h 12m
1 stop
Depart: Wed Nov 1 2017 Return: Fri Nov 3 2017 Trip spans 3 days
Delta
Delta
MDW
SJU
6h 32m
1 stop
SJU
MDW
8h 17m
1 stop
Depart: Tue Aug 29 2017 Return: Sat Sep 9 2017 Trip spans 12 days
Delta
Delta
MDW
SJU
15h 24m
2 stops
SJU
MDW
8h 01m
1 stop
Depart: Mon Aug 14 2017 Return: Wed Aug 23 2017 Trip spans 10 days
Delta
Delta
MDW
SJU
6h 21m
1 stop
SJU
MDW
9h 39m
1 stop
Depart: Sat Jun 10 2017 Return: Sat Jun 24 2017 Trip spans 15 days
Delta
Delta
MDW
HAV
17h 25m
2 stops
HAV
MDW
7h 24m
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
$334
Destination

San Juan
$382
Saint Thomas Island
$348
Havana
$334
Airlines