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 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 18 2017 Return: Tue Oct 24 2017 Trip spans 7 days
Delta
Delta
SJU
MDW
10h 37m
2 stops
MDW
SJU
13h 53m
2 stops
Depart: Thu Oct 5 2017 Return: Tue Oct 10 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
9h 53m
1 stop
MDW
SJU
13h 53m
2 stops
Depart: Wed Nov 1 2017 Return: Wed Nov 8 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
15h 43m
2 stops
MDW
SJU
14h 04m
2 stops
Depart: Fri Dec 1 2017 Return: Mon Dec 4 2017 Trip spans 4 days
Delta
Delta
SJU
MDW
16h 15m
2 stops
MDW
SJU
6h 54m
1 stop
Depart: Thu Sep 14 2017 Return: Mon Sep 18 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
8h 25m
1 stop
MDW
SJU
6h 44m
1 stop
Depart: Thu Sep 28 2017 Return: Tue Oct 3 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
7h 31m
1 stop
MDW
SJU
6h 32m
1 stop
Depart: Thu Oct 19 2017 Return: Mon Oct 23 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
9h 21m
1 stop
MDW
SJU
6h 22m
1 stop
Depart: Wed Jan 17 2018 Return: Wed Jan 24 2018 Trip spans 8 days
Delta
Delta
SJU
MDW
8h 23m
1 stop
MDW
SJU
12h 06m
2 stops
Depart: Thu Sep 21 2017 Return: Sun Sep 24 2017 Trip spans 4 days
Delta
Delta
SJU
MDW
7h 31m
1 stop
MDW
SJU
6h 23m
1 stop
Depart: Fri Nov 3 2017 Return: Sun Nov 5 2017 Trip spans 3 days
Delta
Delta
SJU
MDW
6h 42m
1 stop
MDW
SJU
6h 32m
1 stop
Depart: Wed Dec 20 2017 Return: Mon Jan 8 2018 Trip spans 20 days
Delta
Delta
SJU
MDW
9h 38m
1 stop
MDW
SJU
8h 34m
1 stop
Depart: Wed Dec 20 2017 Return: Wed Jan 3 2018 Trip spans 15 days
Delta
Delta
MBJ
MDW
7h 53m
1 stop
MDW
MBJ
9h 30m
1 stop
Depart: Tue Aug 22 2017 Return: Tue Aug 29 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
9h 15m
1 stop
MDW
SJU
7h 35m
1 stop
Depart: Thu Oct 26 2017 Return: Mon Oct 30 2017 Trip spans 5 days
Delta
Delta
NAS
MDW
9h 18m
1 stop
MDW
NAS
4h 42m
1 stop
Depart: Fri Aug 4 2017 Return: Mon Aug 14 2017 Trip spans 11 days
Delta
Delta
SJU
MDW
8h 30m
1 stop
MDW
SJU
6h 21m
1 stop
Depart: Fri Sep 1 2017 Return: Tue Sep 5 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
9h 35m
1 stop
MDW
SJU
6h 23m
1 stop
Depart: Tue Aug 15 2017 Return: Tue Aug 22 2017 Trip spans 8 days
Delta
Delta
NAS
MDW
8h 31m
2 stops
MDW
NAS
12h 19m
2 stops
Depart: Tue Aug 15 2017 Return: Sun Aug 20 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
9h 15m
1 stop
MDW
SJU
7h 47m
1 stop
Depart: Sat Aug 5 2017 Return: Tue Aug 8 2017 Trip spans 4 days
Delta
Delta
STT
MDW
8h 11m
1 stop
MDW
STT
6h 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
$438
San Juan
$357
Saint Thomas Island
$348
Montego Bay
$408
Destination

Chicago
$348
Airlines