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: Mon Dec 11 2017 Return: Tue Dec 19 2017 Trip spans 9 days
Multiple Airlines
Multiple Airlines
SJU
MDW
26h 36m
2 stops
MDW
SJU
7h 27m
1 stop
Depart: Tue Feb 6 2018 Return: Tue Feb 20 2018 Trip spans 15 days
Delta
Delta
SJU
MDW
7h 53m
1 stop
MDW
SJU
7h 52m
1 stop
Depart: Wed Dec 13 2017 Return: Tue Dec 19 2017 Trip spans 7 days
Multiple Airlines
Multiple Airlines
SJU
MDW
20h 23m
2 stops
MDW
SJU
7h 27m
1 stop
Depart: Wed Feb 21 2018 Return: Tue Feb 27 2018 Trip spans 7 days
Delta
Delta
SJU
MDW
8h 20m
1 stop
MDW
SJU
8h 14m
1 stop
Depart: Thu Feb 22 2018 Return: Thu Mar 1 2018 Trip spans 8 days
Delta
Delta
SJU
MDW
9h 18m
1 stop
MDW
SJU
8h 14m
1 stop
Depart: Fri Jan 12 2018 Return: Tue Jan 16 2018 Trip spans 5 days
Delta
Delta
SJU
MDW
9h 25m
1 stop
MDW
SJU
6h 22m
1 stop
Depart: Fri Jan 19 2018 Return: Tue Jan 23 2018 Trip spans 5 days
Delta
Delta
SJU
MDW
7h 53m
1 stop
MDW
SJU
8h 34m
1 stop
Depart: Thu Jan 25 2018 Return: Sat Jan 27 2018 Trip spans 3 days
Delta
Delta
SJU
MDW
9h 25m
1 stop
MDW
SJU
6h 22m
1 stop
Depart: Sat Feb 24 2018 Return: Sun Mar 4 2018 Trip spans 9 days
Multiple Airlines
Multiple Airlines
SJU
MDW
20h 38m
2 stops
MDW
SJU
7h 20m
1 stop
Depart: Thu Mar 1 2018 Return: Mon Mar 5 2018 Trip spans 5 days
Delta
Delta
SJU
MDW
9h 18m
1 stop
MDW
SJU
7h 52m
1 stop
Depart: Tue Apr 17 2018 Return: Sun Apr 22 2018 Trip spans 6 days
Delta
Delta
SJU
MDW
8h 03m
1 stop
MDW
SJU
7h 59m
1 stop
Depart: Thu Jan 11 2018 Return: Sun Jan 14 2018 Trip spans 4 days
Delta
Delta
SJU
MDW
7h 53m
1 stop
MDW
SJU
6h 49m
1 stop
Depart: Sun Dec 24 2017 Return: Wed Jan 3 2018 Trip spans 11 days
Multiple Airlines
Multiple Airlines
SJU
MDW
13h 43m
2 stops
MDW
SJU
26h 29m
2 stops
Depart: Thu Apr 19 2018 Return: Sun Apr 22 2018 Trip spans 4 days
Delta
Delta
SJU
MDW
9h 24m
1 stop
MDW
SJU
6h 22m
1 stop
Depart: Sat Feb 24 2018 Return: Sat Mar 3 2018 Trip spans 8 days
Multiple Airlines
Multiple Airlines
SJU
MDW
21h 37m
2 stops
MDW
SJU
10h 20m
2 stops
Depart: Fri Dec 29 2017 Return: Tue Jan 2 2018 Trip spans 5 days
Delta
Delta
NAS
MDW
10h 24m
1 stop
MDW
NAS
4h 58m
1 stop
Depart: Thu Dec 7 2017 Return: Mon Dec 11 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
6h 45m
1 stop
MDW
SJU
6h 22m
1 stop
Depart: Tue Dec 5 2017 Return: Fri Jan 19 2018 Trip spans 46 days
Delta
Delta
SJU
MDW
8h 00m
1 stop
MDW
SJU
7h 52m
1 stop
Depart: Wed Dec 27 2017 Return: Sat Jan 6 2018 Trip spans 11 days
Multiple Airlines
Multiple Airlines
SJU
MDW
12h 42m
2 stops
MDW
SJU
16h 39m
2 stops
Depart: Wed Dec 6 2017 Return: Wed Dec 13 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
6h 45m
1 stop
MDW
SJU
6h 34m
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 and someone from our team will get back to you promptly.

Airports
Origin

Nassau
$423
San Juan
$344
Destination

Chicago
$344
Airlines