Find Cheap Flights from Caribbean to Chicago Midway

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 Caribbean to Chicago Midway

(Round-trip)
Depart: Thu Sep 28 2017 Return: Tue Oct 3 2017 Trip spans 6 days
Delta
Delta
STT
MDW
7h 37m
1 stop
MDW
STT
6h 27m
1 stop
Depart: Thu Oct 19 2017 Return: Tue Oct 24 2017 Trip spans 6 days
Delta
Delta
STT
MDW
9h 37m
1 stop
MDW
STT
6h 27m
1 stop
Depart: Wed Oct 4 2017 Return: Tue Oct 10 2017 Trip spans 7 days
Delta
Delta
SJU
MDW
8h 17m
1 stop
MDW
SJU
6h 24m
1 stop
Depart: Thu Oct 5 2017 Return: Tue Oct 10 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
8h 17m
1 stop
MDW
SJU
6h 22m
1 stop
Depart: Tue Sep 12 2017 Return: Fri Sep 15 2017 Trip spans 4 days
Delta
Delta
SJU
MDW
9h 48m
1 stop
MDW
SJU
6h 32m
1 stop
Depart: Thu Aug 24 2017 Return: Fri Sep 8 2017 Trip spans 16 days
Delta
Delta
SJU
MDW
9h 39m
1 stop
MDW
SJU
6h 22m
1 stop
Depart: Fri Sep 29 2017 Return: Sun Oct 1 2017 Trip spans 3 days
Delta
Delta
SJU
MDW
9h 53m
1 stop
MDW
SJU
6h 24m
1 stop
Depart: Fri Nov 10 2017 Return: Mon Nov 13 2017 Trip spans 4 days
Delta
Delta
SJU
MDW
8h 03m
1 stop
MDW
SJU
6h 22m
1 stop
Depart: Thu Oct 5 2017 Return: Tue Oct 10 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
8h 17m
1 stop
MDW
SJU
6h 22m
1 stop
Depart: Tue Jul 18 2017 Return: Tue Aug 1 2017 Trip spans 15 days
Delta
Delta
SJU
MDW
9h 36m
1 stop
MDW
SJU
7h 15m
1 stop
Depart: Thu Aug 10 2017 Return: Mon Aug 14 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
9h 36m
1 stop
MDW
SJU
6h 21m
1 stop
Depart: Fri Sep 8 2017 Return: Sat Sep 16 2017 Trip spans 9 days
Delta
Delta
SJU
MDW
9h 39m
1 stop
MDW
SJU
6h 22m
1 stop
Depart: Sat Sep 30 2017 Return: Sat Oct 7 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
8h 15m
1 stop
MDW
SJU
8h 34m
1 stop
Depart: Thu Jul 6 2017 Return: Mon Jul 10 2017 Trip spans 5 days
Delta
Delta
NAS
MDW
14h 06m
1 stop
MDW
NAS
5h 17m
1 stop
Depart: Thu Aug 10 2017 Return: Mon Aug 21 2017 Trip spans 12 days
Delta
Delta
STT
MDW
8h 15m
1 stop
MDW
STT
6h 22m
1 stop
Depart: Tue Jul 4 2017 Return: Sat Aug 26 2017 Trip spans 54 days
Delta
Delta
MBJ
MDW
7h 41m
1 stop
MDW
MBJ
12h 40m
2 stops
Depart: Thu Jul 27 2017 Return: Wed Aug 9 2017 Trip spans 14 days
Delta
Delta
SJU
MDW
8h 30m
1 stop
MDW
SJU
7h 15m
1 stop
Depart: Tue Aug 1 2017 Return: Tue Aug 8 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
7h 47m
1 stop
MDW
SJU
6h 15m
1 stop
Depart: Thu Nov 9 2017 Return: Thu Nov 16 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
7h 48m
1 stop
MDW
SJU
8h 34m
1 stop
Depart: Mon Jul 17 2017 Return: Sun Jul 23 2017 Trip spans 7 days
Delta
Delta
NAS
MDW
12h 15m
1 stop
MDW
NAS
11h 57m
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

Nassau
$438
San Juan
$382
Saint Thomas Island
$348
Montego Bay
$470
Destination

Chicago
$348
Airlines