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: Mon Aug 21 2017 Return: Fri Aug 25 2017 Trip spans 5 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
9h 05m
1 stop
Depart: Tue Nov 7 2017 Return: Tue Nov 14 2017 Trip spans 8 days
Delta
Delta
MDW
HAV
4h 55m
1 stop
HAV
MDW
7h 28m
1 stop
Depart: Tue Nov 21 2017 Return: Thu Nov 30 2017 Trip spans 10 days
Delta
Delta
MDW
HAV
4h 55m
1 stop
HAV
MDW
7h 08m
1 stop
Depart: Tue Jan 23 2018 Return: Tue Jan 30 2018 Trip spans 8 days
Delta
Delta
MDW
HAV
4h 55m
1 stop
HAV
MDW
8h 03m
1 stop
Depart: Sat Sep 2 2017 Return: Mon Sep 11 2017 Trip spans 10 days
Delta
Delta
MDW
HAV
16h 30m
2 stops
HAV
MDW
12h 35m
2 stops
Depart: Sat Sep 16 2017 Return: Wed Sep 20 2017 Trip spans 5 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
12h 35m
2 stops
Depart: Sat Oct 7 2017 Return: Tue Oct 10 2017 Trip spans 4 days
Delta
Delta
MDW
HAV
16h 50m
2 stops
HAV
MDW
19h 01m
2 stops
Depart: Wed Dec 6 2017 Return: Wed Dec 13 2017 Trip spans 8 days
Delta
Delta
MDW
HAV
16h 50m
2 stops
HAV
MDW
12h 33m
2 stops
Depart: Fri Oct 13 2017 Return: Mon Oct 16 2017 Trip spans 4 days
Delta
Delta
MDW
HAV
5h 35m
1 stop
HAV
MDW
12h 47m
2 stops
Depart: Fri Dec 1 2017 Return: Sat Dec 9 2017 Trip spans 9 days
Delta
Delta
MDW
HAV
4h 55m
1 stop
HAV
MDW
9h 16m
1 stop
Depart: Thu Sep 21 2017 Return: Sun Sep 24 2017 Trip spans 4 days
Delta
Delta
MDW
HAV
16h 30m
2 stops
HAV
MDW
9h 20m
1 stop
Depart: Thu Aug 10 2017 Return: Wed Aug 16 2017 Trip spans 7 days
Delta
Delta
MDW
HAV
15h 53m
1 stop
HAV
MDW
9h 05m
1 stop
Depart: Thu Jan 11 2018 Return: Mon Jan 15 2018 Trip spans 5 days
Delta
Delta
MDW
HAV
4h 55m
1 stop
HAV
MDW
8h 03m
1 stop
Depart: Sat Aug 12 2017 Return: Sat Aug 19 2017 Trip spans 8 days
Delta
Delta
MDW
NAS
5h 00m
1 stop
NAS
MDW
9h 12m
1 stop
Depart: Fri Sep 15 2017 Return: Tue Sep 19 2017 Trip spans 5 days
Delta
Delta
MDW
NAS
4h 50m
1 stop
NAS
MDW
5h 52m
1 stop
Depart: Sat Sep 30 2017 Return: Wed Oct 4 2017 Trip spans 5 days
Delta
Delta
MDW
NAS
11h 54m
1 stop
NAS
MDW
6h 32m
1 stop
Depart: Sat Oct 7 2017 Return: Tue Oct 10 2017 Trip spans 4 days
Delta
Delta
MDW
NAS
12h 52m
1 stop
NAS
MDW
15h 57m
1 stop
Depart: Sat Oct 21 2017 Return: Sat Oct 28 2017 Trip spans 8 days
Delta
Delta
MDW
NAS
12h 52m
1 stop
NAS
MDW
8h 36m
1 stop
Depart: Wed Oct 25 2017 Return: Tue Oct 31 2017 Trip spans 7 days
Delta
Delta
MDW
NAS
8h 42m
1 stop
NAS
MDW
6h 55m
1 stop
Depart: Wed Nov 1 2017 Return: Tue Nov 7 2017 Trip spans 7 days
Delta
Delta
MDW
NAS
7h 32m
1 stop
NAS
MDW
11h 28m
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
$328
Destination

Nassau
$447
Havana
$328
Airlines