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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Book cheap flights from Caribbean to Chicago Midway

(Round-trip)
Depart: Mon Oct 2 2017 Return: Thu Oct 12 2017 Trip spans 11 days
Delta
Delta
SJU
MDW
10h 45m
2 stops
MDW
SJU
8h 36m
1 stop
Depart: Thu Oct 12 2017 Return: Tue Oct 24 2017 Trip spans 13 days
Delta
Delta
SJU
MDW
8h 14m
1 stop
MDW
SJU
13h 40m
2 stops
Depart: Fri Oct 6 2017 Return: Wed Oct 11 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
9h 36m
1 stop
MDW
SJU
7h 31m
1 stop
Depart: Sat Oct 14 2017 Return: Mon Oct 16 2017 Trip spans 3 days
Delta
Delta
SJU
MDW
7h 08m
1 stop
MDW
SJU
6h 41m
1 stop
Depart: Thu Feb 1 2018 Return: Fri Mar 2 2018 Trip spans 30 days
Delta
Delta
SJU
MDW
9h 18m
1 stop
MDW
SJU
7h 42m
1 stop
Depart: Sat Sep 30 2017 Return: Sun Oct 22 2017 Trip spans 23 days
Delta
Delta
SJU
MDW
10h 08m
2 stops
MDW
SJU
6h 11m
1 stop
Depart: Tue Oct 3 2017 Return: Tue Oct 17 2017 Trip spans 15 days
Delta
Delta
SJU
MDW
11h 59m
2 stops
MDW
SJU
13h 40m
2 stops
Depart: Thu Oct 19 2017 Return: Thu Nov 9 2017 Trip spans 22 days
Delta
Delta
SJU
MDW
9h 20m
1 stop
MDW
SJU
6h 38m
1 stop
Depart: Fri Nov 17 2017 Return: Mon Nov 27 2017 Trip spans 11 days
Delta
Delta
SJU
MDW
9h 30m
1 stop
MDW
SJU
8h 45m
1 stop
Depart: Tue Oct 3 2017 Return: Thu Nov 2 2017 Trip spans 31 days
Delta
Delta
SJU
MDW
11h 59m
2 stops
MDW
SJU
8h 36m
1 stop
Depart: Tue Oct 3 2017 Return: Fri Dec 1 2017 Trip spans 60 days
Delta
Delta
SJU
MDW
11h 59m
2 stops
MDW
SJU
6h 22m
1 stop
Depart: Thu Sep 28 2017 Return: Wed Nov 1 2017 Trip spans 35 days
Delta
Delta
SJU
MDW
10h 50m
2 stops
MDW
SJU
7h 31m
1 stop
Depart: Thu Oct 5 2017 Return: Thu Nov 2 2017 Trip spans 29 days
Delta
Delta
SJU
MDW
9h 20m
1 stop
MDW
SJU
8h 36m
1 stop
Depart: Thu Dec 21 2017 Return: Sun Dec 31 2017 Trip spans 11 days
Delta
Delta
SJU
MDW
8h 41m
1 stop
MDW
SJU
6h 22m
1 stop
Depart: Mon Oct 2 2017 Return: Fri Oct 6 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
10h 45m
2 stops
MDW
SJU
8h 36m
1 stop
Depart: Tue Sep 26 2017 Return: Mon Oct 2 2017 Trip spans 7 days
Delta
Delta
SJU
MDW
10h 50m
2 stops
MDW
SJU
6h 41m
1 stop
Depart: Fri Oct 6 2017 Return: Mon Oct 9 2017 Trip spans 4 days
Delta
Delta
GCM
MDW
9h 00m
1 stop
MDW
GCM
6h 40m
1 stop
Depart: Tue Nov 21 2017 Return: Mon Nov 27 2017 Trip spans 7 days
Delta
Delta
SJU
MDW
9h 49m
1 stop
MDW
SJU
6h 53m
1 stop
Depart: Fri Sep 29 2017 Return: Sun Oct 1 2017 Trip spans 3 days
Delta
Delta
SJU
MDW
12h 00m
2 stops
MDW
SJU
6h 11m
1 stop
Depart: Sat Dec 23 2017 Return: Tue Jan 2 2018 Trip spans 11 days
Delta
Delta
SJU
MDW
9h 22m
1 stop
MDW
SJU
7h 52m
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

San Juan
$375
George Town
$534
Destination

Chicago
$375
Airlines