Find Deals on 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
Students
under 26
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: Wed Jan 18 2017 Return: Mon Jan 23 2017 Trip spans 6 days
Delta
Delta
MDW
HAV
6h 25m
1 stop
HAV
MDW
9h 21m
1 stop
Depart: Mon Jan 23 2017 Return: Mon Jan 30 2017 Trip spans 8 days
Major Airline
Major Airline
MDW
STX
2h 17m
nonstop
STX
MDW
6h 17m
nonstop
Depart: Tue Jan 24 2017 Return: Fri Feb 3 2017 Trip spans 11 days
Delta
Delta
MDW
HAV
6h 25m
1 stop
HAV
MDW
6h 37m
1 stop
Depart: Mon Feb 6 2017 Return: Fri Feb 10 2017 Trip spans 5 days
Delta
Delta
MDW
HAV
6h 25m
1 stop
HAV
MDW
6h 37m
1 stop
Depart: Fri Jan 27 2017 Return: Tue Jan 31 2017 Trip spans 5 days
Major Airline
Major Airline
MDW
PUJ
4h 25m
nonstop
PUJ
MDW
5h 10m
nonstop
Depart: Wed Feb 8 2017 Return: Wed Feb 15 2017 Trip spans 8 days
Delta
Delta
MDW
HAV
6h 25m
1 stop
HAV
MDW
6h 37m
1 stop
Depart: Wed Mar 8 2017 Return: Mon Mar 13 2017 Trip spans 5 days
Delta
Delta
MDW
HAV
5h 20m
1 stop
HAV
MDW
6h 37m
1 stop
Depart: Wed Mar 15 2017 Return: Wed Mar 22 2017 Trip spans 8 days
Delta
Delta
MDW
HAV
5h 20m
1 stop
HAV
MDW
6h 37m
1 stop
Depart: Wed Apr 19 2017 Return: Sat Apr 29 2017 Trip spans 11 days
Delta
Delta
MDW
HAV
6h 25m
1 stop
HAV
MDW
6h 37m
1 stop
Depart: Mon May 1 2017 Return: Sun May 7 2017 Trip spans 7 days
Delta
Delta
MDW
HAV
6h 25m
1 stop
HAV
MDW
6h 36m
1 stop
Depart: Tue May 2 2017 Return: Sat May 6 2017 Trip spans 5 days
Delta
Delta
MDW
HAV
5h 20m
1 stop
HAV
MDW
6h 17m
1 stop
Depart: Sat May 6 2017 Return: Sat May 13 2017 Trip spans 8 days
Delta
Delta
MDW
HAV
6h 25m
1 stop
HAV
MDW
6h 37m
1 stop
Depart: Wed Jun 21 2017 Return: Wed Jun 28 2017 Trip spans 8 days
Delta
Delta
MDW
HAV
20h 05m
2 stops
HAV
MDW
12h 38m
2 stops
Depart: Thu Jun 29 2017 Return: Wed Jul 5 2017 Trip spans 7 days
Delta
Delta
MDW
HAV
21h 45m
2 stops
HAV
MDW
7h 18m
1 stop
Depart: Tue Jan 17 2017 Return: Tue Jan 24 2017 Trip spans 8 days
Major Airline
Major Airline
MDW
SKB
2h 29m
2 stops
SKB
MDW
6h 29m
2 stops
Depart: Fri Jan 6 2017 Return: Tue Jan 17 2017 Trip spans 12 days
Delta
Delta
MDW
STT
6h 58m
1 stop
STT
MDW
7h 58m
1 stop
Depart: Sun Jan 15 2017 Return: Thu Jan 19 2017 Trip spans 5 days
Delta
Delta
MDW
PUJ
8h 45m
1 stop
PUJ
MDW
10h 47m
1 stop
Depart: Tue Mar 14 2017 Return: Tue Mar 21 2017 Trip spans 8 days
Delta
Delta
MDW
PUJ
6h 40m
1 stop
PUJ
MDW
15h 07m
1 stop
Depart: Thu Dec 29 2016 Return: Mon Jan 2 2017 Trip spans 5 days
Major Airline
Major Airline
MDW
NAS
1h 35m
nonstop
NAS
MDW
3h 35m
nonstop
Depart: Wed Mar 15 2017 Return: Tue Mar 21 2017 Trip spans 7 days
Delta
Delta
MDW
PUJ
11h 50m
1 stop
PUJ
MDW
15h 07m
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
$321
Destination

Nassau
$997
Saint Thomas Island
$335
Christiansted
$351
Basseterre
$786
Punta Cana
$336
Havana
$321
Airlines