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 Oct 5 2017 Return: Tue Oct 10 2017 Trip spans 6 days
Multiple Airlines
Multiple Airlines
MDW
SJU
7h 53m
1 stop
SJU
MDW
8h 10m
1 stop
Depart: Thu Oct 12 2017 Return: Tue Oct 17 2017 Trip spans 6 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
9h 05m
1 stop
Depart: Tue Oct 17 2017 Return: Tue Oct 24 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
MDW
SJU
7h 38m
1 stop
SJU
MDW
8h 10m
1 stop
Depart: Sun Oct 22 2017 Return: Thu Oct 26 2017 Trip spans 5 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
9h 05m
1 stop
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: Tue Nov 7 2017 Return: Tue Nov 14 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
MDW
SJU
7h 34m
1 stop
SJU
MDW
19h 40m
2 stops
Depart: Thu Nov 9 2017 Return: Mon Nov 13 2017 Trip spans 5 days
Delta
Delta
MDW
HAV
20h 53m
1 stop
HAV
MDW
8h 50m
1 stop
Depart: Tue Oct 10 2017 Return: Fri Oct 13 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
MDW
SJU
7h 38m
1 stop
SJU
MDW
21h 24m
2 stops
Depart: Sat Oct 7 2017 Return: Sat Oct 14 2017 Trip spans 8 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
9h 04m
1 stop
Depart: Thu Nov 2 2017 Return: Tue Nov 7 2017 Trip spans 6 days
Multiple Airlines
Multiple Airlines
MDW
SJU
7h 34m
1 stop
SJU
MDW
8h 30m
1 stop
Depart: Fri Oct 27 2017 Return: Sun Oct 29 2017 Trip spans 3 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
9h 05m
1 stop
Depart: Thu Oct 26 2017 Return: Tue Nov 7 2017 Trip spans 13 days
Multiple Airlines
Multiple Airlines
MDW
SJU
7h 38m
1 stop
SJU
MDW
16h 46m
2 stops
Depart: Fri Oct 13 2017 Return: Fri Oct 20 2017 Trip spans 8 days
Delta
Delta
MDW
STT
6h 25m
1 stop
STT
MDW
7h 15m
1 stop
Depart: Sat Oct 7 2017 Return: Tue Oct 10 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
MDW
SJU
24h 21m
2 stops
SJU
MDW
8h 10m
1 stop
Depart: Sat Nov 11 2017 Return: Sat Nov 18 2017 Trip spans 8 days
Delta
Delta
MDW
STT
7h 30m
1 stop
STT
MDW
8h 08m
1 stop
Depart: Thu Oct 5 2017 Return: Sun Oct 8 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
MDW
SJU
7h 53m
1 stop
SJU
MDW
21h 25m
2 stops
Depart: Sat Nov 18 2017 Return: Fri Nov 24 2017 Trip spans 7 days
Delta
Delta
MDW
STT
6h 15m
1 stop
STT
MDW
9h 28m
1 stop
Depart: Sat Dec 2 2017 Return: Sat Dec 9 2017 Trip spans 8 days
Delta
Delta
MDW
STT
7h 21m
1 stop
STT
MDW
8h 40m
1 stop
Depart: Mon Sep 25 2017 Return: Tue Oct 17 2017 Trip spans 23 days
Multiple Airlines
Multiple Airlines
MDW
SJU
14h 51m
2 stops
SJU
MDW
8h 10m
1 stop
Depart: Tue Dec 5 2017 Return: Tue Dec 12 2017 Trip spans 8 days
Delta
Delta
MDW
STT
6h 27m
1 stop
STT
MDW
8h 00m
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
$307
Destination

San Juan
$307
Saint Thomas Island
$348
Havana
$328
Airlines