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.
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 Caribbean

(Round-trip)
Depart: Thu Jan 18 2018 Return: Sun Jan 21 2018 Trip spans 4 days
Delta
Delta
MDW
HAV
4h 55m
1 stop
HAV
MDW
7h 33m
1 stop
Depart: Sat Feb 3 2018 Return: Thu Feb 8 2018 Trip spans 6 days
Multiple Airlines
Multiple Airlines
MDW
SJU
30h 11m
2 stops
SJU
MDW
21h 04m
1 stop
Depart: Thu Jan 11 2018 Return: Sun Jan 14 2018 Trip spans 4 days
Multiple Airlines
Multiple Airlines
MDW
HAV
22h 55m
1 stop
HAV
MDW
25h 50m
1 stop
Depart: Fri Jan 19 2018 Return: Thu Jan 25 2018 Trip spans 7 days
Delta
Delta
MDW
HAV
4h 55m
1 stop
HAV
MDW
7h 33m
1 stop
Depart: Mon Feb 5 2018 Return: Mon Feb 12 2018 Trip spans 8 days
Delta
Delta
MDW
HAV
4h 55m
1 stop
HAV
MDW
7h 33m
1 stop
Depart: Sat Feb 3 2018 Return: Thu Feb 8 2018 Trip spans 6 days
Multiple Airlines
Multiple Airlines
MDW
SJU
30h 11m
2 stops
SJU
MDW
21h 04m
1 stop
Depart: Sat Dec 9 2017 Return: Sun Dec 17 2017 Trip spans 9 days
Delta
Delta
MDW
HAV
19h 45m
2 stops
HAV
MDW
7h 55m
1 stop
Depart: Thu Dec 7 2017 Return: Tue Dec 12 2017 Trip spans 6 days
Multiple Airlines
Multiple Airlines
MDW
SJU
7h 34m
1 stop
SJU
MDW
16h 57m
2 stops
Depart: Mon Dec 11 2017 Return: Sun Dec 17 2017 Trip spans 7 days
Delta
Delta
MDW
HAV
18h 05m
2 stops
HAV
MDW
19h 09m
2 stops
Depart: Sun Jan 21 2018 Return: Thu Jan 25 2018 Trip spans 5 days
Delta
Delta
MDW
HAV
16h 45m
2 stops
HAV
MDW
7h 33m
1 stop
Depart: Sat Feb 24 2018 Return: Thu Mar 1 2018 Trip spans 6 days
Multiple Airlines
Multiple Airlines
MDW
SJU
20h 30m
1 stop
SJU
MDW
19h 15m
1 stop
Depart: Tue Dec 5 2017 Return: Mon Dec 11 2017 Trip spans 7 days
Multiple Airlines
Multiple Airlines
MDW
SJU
7h 34m
1 stop
SJU
MDW
16h 57m
2 stops
Depart: Sun Dec 10 2017 Return: Thu Dec 21 2017 Trip spans 12 days
Delta
Delta
MDW
HAV
16h 15m
1 stop
HAV
MDW
9h 02m
1 stop
Depart: Sat Mar 3 2018 Return: Tue Mar 6 2018 Trip spans 4 days
Multiple Airlines
Multiple Airlines
MDW
SJU
32h 28m
2 stops
SJU
MDW
22h 03m
2 stops
Depart: Thu Dec 14 2017 Return: Sun Dec 17 2017 Trip spans 4 days
Delta
Delta
MDW
HAV
18h 25m
1 stop
HAV
MDW
7h 55m
1 stop
Depart: Wed Jan 10 2018 Return: Sat Jan 20 2018 Trip spans 11 days
Delta
Delta
MDW
HAV
4h 55m
1 stop
HAV
MDW
8h 38m
1 stop
Depart: Wed Feb 21 2018 Return: Thu Mar 1 2018 Trip spans 9 days
Multiple Airlines
Multiple Airlines
MDW
SJU
25h 26m
2 stops
SJU
MDW
19h 15m
1 stop
Depart: Thu Dec 7 2017 Return: Tue Dec 12 2017 Trip spans 6 days
Delta
Delta
MDW
STT
6h 41m
1 stop
STT
MDW
8h 04m
1 stop
Depart: Sat Feb 17 2018 Return: Fri Feb 23 2018 Trip spans 7 days
Multiple Airlines
Multiple Airlines
MDW
SJU
32h 28m
2 stops
SJU
MDW
20h 38m
2 stops
Depart: Mon Jan 29 2018 Return: Mon Feb 5 2018 Trip spans 8 days
Delta
Delta
MDW
STT
6h 27m
1 stop
STT
MDW
8h 31m
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 and someone from our team will get back to you promptly.

Airports
Origin

Chicago
$286
Destination

San Juan
$318
Saint Thomas Island
$348
Havana
$286
Airlines