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: Mon Oct 2 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
6h 42m
1 stop
MDW
SJU
7h 52m
1 stop
Depart: Tue May 2 2017 Return: Sun May 7 2017 Trip spans 6 days
Major Airline
Major Airline
SJU
MDW
5h 06m
nonstop
MDW
SJU
3h 06m
nonstop
Depart: Tue Oct 3 2017 Return: Sat Oct 7 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
16h 48m
2 stops
MDW
SJU
17h 58m
2 stops
Depart: Tue Aug 29 2017 Return: Wed Sep 6 2017 Trip spans 9 days
Delta
Delta
SJU
MDW
6h 49m
1 stop
MDW
SJU
15h 13m
2 stops
Depart: Wed Jun 7 2017 Return: Mon Jun 19 2017 Trip spans 13 days
Delta
Delta
SJU
MDW
9h 05m
1 stop
MDW
SJU
7h 22m
1 stop
Depart: Tue Aug 15 2017 Return: Mon Aug 21 2017 Trip spans 7 days
Delta
Delta
SJU
MDW
7h 29m
1 stop
MDW
SJU
6h 54m
1 stop
Depart: Mon May 15 2017 Return: Thu May 18 2017 Trip spans 4 days
Delta
Delta
NAS
MDW
11h 39m
1 stop
MDW
NAS
6h 46m
1 stop
Depart: Thu Jun 1 2017 Return: Sun Jun 4 2017 Trip spans 4 days
Delta
Delta
NAS
MDW
5h 45m
1 stop
MDW
NAS
5h 00m
1 stop
Depart: Wed Jul 19 2017 Return: Tue Aug 15 2017 Trip spans 28 days
Delta
Delta
STT
MDW
8h 08m
1 stop
MDW
STT
6h 34m
1 stop
Depart: Thu Jul 6 2017 Return: Mon Jul 10 2017 Trip spans 5 days
Delta
Delta
NAS
MDW
8h 17m
1 stop
MDW
NAS
14h 23m
1 stop
Depart: Wed May 17 2017 Return: Sat Jul 8 2017 Trip spans 53 days
Delta
Delta
MBJ
MDW
10h 28m
1 stop
MDW
MBJ
12h 40m
1 stop
Depart: Thu Jun 8 2017 Return: Mon Jun 19 2017 Trip spans 12 days
Delta
Delta
SJU
MDW
7h 00m
1 stop
MDW
SJU
7h 22m
1 stop
Depart: Sat Sep 30 2017 Return: Sat Oct 7 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
8h 01m
1 stop
MDW
SJU
8h 34m
1 stop
Depart: Thu Oct 5 2017 Return: Mon Oct 9 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
9h 39m
1 stop
MDW
SJU
6h 54m
1 stop
Depart: Wed May 24 2017 Return: Wed May 31 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
7h 38m
1 stop
MDW
SJU
6h 25m
1 stop
Depart: Tue Jul 11 2017 Return: Tue Jul 18 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
8h 52m
1 stop
MDW
SJU
7h 52m
1 stop
Depart: Fri May 19 2017 Return: Mon May 22 2017 Trip spans 4 days
Delta
Delta
GCM
MDW
8h 45m
1 stop
MDW
GCM
5h 15m
1 stop
Depart: Wed Jun 14 2017 Return: Wed Jun 21 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
12h 54m
2 stops
MDW
SJU
6h 26m
1 stop
Depart: Wed Aug 2 2017 Return: Mon Aug 21 2017 Trip spans 20 days
Delta
Delta
MBJ
MDW
10h 53m
1 stop
MDW
MBJ
15h 40m
1 stop
Depart: Thu Jun 22 2017 Return: Mon Jun 26 2017 Trip spans 5 days
Delta
Delta
GCM
MDW
7h 23m
1 stop
MDW
GCM
16h 47m
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
$442
San Juan
$362
Saint Thomas Island
$448
Montego Bay
$457
George Town
$488
Destination

Chicago
$362
Airlines