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 3 2017 Return: Sun Feb 5 2017 Trip spans 3 days
Delta
Delta
SJU
MDW
17h 06m
2 stops
MDW
SJU
8h 14m
1 stop
Depart: Thu Jan 12 2017 Return: Sun Jan 15 2017 Trip spans 4 days
Major Airline
Major Airline
NAS
MDW
3h 35m
1 stop
MDW
NAS
1h 35m
1 stop
Depart: Thu Dec 8 2016 Return: Tue Jan 17 2017 Trip spans 41 days
Delta
Delta
SJU
MDW
7h 36m
1 stop
MDW
SJU
13h 15m
2 stops
Depart: Sat Dec 24 2016 Return: Thu Jan 5 2017 Trip spans 13 days
Delta
Delta
STT
MDW
8h 52m
1 stop
MDW
STT
7h 54m
1 stop
Depart: Tue Apr 4 2017 Return: Wed Apr 12 2017 Trip spans 9 days
Delta
Delta
SJU
MDW
6h 48m
1 stop
MDW
SJU
16h 39m
2 stops
Depart: Tue Jan 24 2017 Return: Tue Jan 31 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
9h 25m
1 stop
MDW
SJU
8h 17m
1 stop
Depart: Thu Jan 26 2017 Return: Sun Jan 29 2017 Trip spans 4 days
Delta
Delta
SJU
MDW
8h 01m
1 stop
MDW
SJU
6h 29m
1 stop
Depart: Wed Feb 1 2017 Return: Mon Feb 6 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
9h 25m
1 stop
MDW
SJU
6h 19m
1 stop
Depart: Thu Mar 9 2017 Return: Wed Mar 15 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
7h 17m
1 stop
MDW
SJU
6h 47m
1 stop
Depart: Tue Mar 14 2017 Return: Mon Mar 20 2017 Trip spans 7 days
Delta
Delta
SJU
MDW
7h 17m
1 stop
MDW
SJU
6h 11m
1 stop
Depart: Tue Apr 4 2017 Return: Mon Apr 10 2017 Trip spans 7 days
Delta
Delta
SJU
MDW
6h 48m
1 stop
MDW
SJU
7h 52m
1 stop
Depart: Fri Jan 13 2017 Return: Tue Jan 17 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
20h 11m
2 stops
MDW
SJU
6h 29m
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
7h 42m
1 stop
Depart: Tue Dec 6 2016 Return: Sun Dec 11 2016 Trip spans 6 days
Delta
Delta
SJU
MDW
7h 59m
1 stop
MDW
SJU
8h 24m
1 stop
Depart: Tue Dec 27 2016 Return: Mon Feb 6 2017 Trip spans 42 days
Delta
Delta
MBJ
MDW
14h 21m
1 stop
MDW
MBJ
7h 58m
1 stop
Depart: Thu Mar 9 2017 Return: Sun Mar 12 2017 Trip spans 4 days
Delta
Delta
MBJ
MDW
13h 52m
1 stop
MDW
MBJ
25h 25m
1 stop
Depart: Wed Jun 14 2017 Return: Wed Jun 21 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
6h 49m
1 stop
MDW
SJU
6h 54m
1 stop
Depart: Wed Jan 18 2017 Return: Fri Jan 20 2017 Trip spans 3 days
Delta
Delta
SJU
MDW
8h 01m
1 stop
MDW
SJU
7h 49m
1 stop
Depart: Tue Apr 18 2017 Return: Sat Apr 22 2017 Trip spans 5 days
Delta
Delta
NAS
MDW
10h 24m
1 stop
MDW
NAS
4h 50m
1 stop
Depart: Fri Apr 21 2017 Return: Wed Apr 26 2017 Trip spans 6 days
Delta
Delta
MBJ
MDW
25h 20m
1 stop
MDW
MBJ
9h 30m
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
$354
San Juan
$310
Saint Thomas Island
$335
Montego Bay
$406
Destination

Chicago
$310
Airlines