Find Deals on 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
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 Caribbean to Chicago Midway

(Round-trip)
Depart: Fri Feb 10 2017 Return: Tue Feb 14 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
8h 01m
1 stop
MDW
SJU
8h 17m
1 stop
Depart: Thu Feb 16 2017 Return: Thu Mar 2 2017 Trip spans 15 days
Delta
Delta
SJU
MDW
8h 07m
1 stop
MDW
SJU
8h 08m
1 stop
Depart: Wed Feb 22 2017 Return: Sun Feb 26 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
7h 19m
1 stop
MDW
SJU
8h 08m
1 stop
Depart: Wed Mar 22 2017 Return: Mon Mar 27 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
8h 55m
1 stop
MDW
SJU
6h 51m
1 stop
Depart: Wed Mar 1 2017 Return: Mon Mar 6 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
7h 46m
1 stop
MDW
SJU
6h 20m
1 stop
Depart: Wed Apr 5 2017 Return: Wed Apr 12 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
8h 11m
1 stop
MDW
SJU
6h 22m
1 stop
Depart: Wed Feb 22 2017 Return: Sun Feb 26 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
7h 19m
1 stop
MDW
SJU
8h 08m
1 stop
Depart: Wed Apr 12 2017 Return: Tue Apr 18 2017 Trip spans 7 days
Delta
Delta
SJU
MDW
8h 11m
1 stop
MDW
SJU
6h 22m
1 stop
Depart: Wed Jun 7 2017 Return: Tue Jun 20 2017 Trip spans 14 days
Delta
Delta
SJU
MDW
6h 40m
1 stop
MDW
SJU
8h 34m
1 stop
Depart: Wed Feb 15 2017 Return: Mon Feb 20 2017 Trip spans 6 days
Delta
Delta
STT
MDW
7h 58m
1 stop
MDW
STT
6h 32m
1 stop
Depart: Thu May 4 2017 Return: Tue May 9 2017 Trip spans 6 days
Delta
Delta
STT
MDW
7h 09m
1 stop
MDW
STT
6h 37m
1 stop
Depart: Sun Jan 29 2017 Return: Sun Feb 12 2017 Trip spans 15 days
Delta
Delta
SJU
MDW
9h 25m
1 stop
MDW
SJU
8h 17m
1 stop
Depart: Wed Mar 15 2017 Return: Sun Mar 19 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
8h 33m
1 stop
MDW
SJU
8h 44m
1 stop
Depart: Tue Jan 31 2017 Return: Mon Feb 13 2017 Trip spans 14 days
Delta
Delta
STT
MDW
7h 58m
1 stop
MDW
STT
7h 48m
1 stop
Depart: Tue Feb 14 2017 Return: Mon Feb 20 2017 Trip spans 7 days
Delta
Delta
MBJ
MDW
7h 47m
1 stop
MDW
MBJ
6h 48m
1 stop
Depart: Fri Jun 2 2017 Return: Mon Jun 5 2017 Trip spans 4 days
Delta
Delta
SJU
MDW
8h 10m
1 stop
MDW
SJU
6h 49m
1 stop
Depart: Wed Jul 26 2017 Return: Wed Aug 2 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
9h 39m
1 stop
MDW
SJU
6h 54m
1 stop
Depart: Thu Feb 9 2017 Return: Sun Feb 12 2017 Trip spans 4 days
Delta
Delta
NAS
MDW
6h 02m
1 stop
MDW
NAS
6h 33m
1 stop
Depart: Sun Mar 12 2017 Return: Mon Mar 13 2017 Trip spans 1 days
Delta
Delta
MBJ
MDW
9h 15m
1 stop
MDW
MBJ
16h 50m
1 stop
Depart: Tue Apr 18 2017 Return: Sat Apr 22 2017 Trip spans 5 days
Delta
Delta
NAS
MDW
8h 17m
1 stop
MDW
NAS
4h 50m
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
$426
San Juan
$308
Saint Thomas Island
$348
Montego Bay
$402
Destination

Chicago
$308
Airlines