Find Cheap Flights from Chicago Midway to Puerto Rico

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 Chicago Midway to Puerto Rico

(Round-trip)
Depart: Tue Nov 14 2017 Return: Thu Nov 16 2017 Trip spans 3 days
Multiple Airlines
Multiple Airlines
MDW
12:00a
SJU
7:34a
7h 34m
1 stop
SJU
12:00a
MDW
8:30a
8h 30m
1 stop
Depart: Thu Oct 26 2017 Return: Thu Nov 9 2017 Trip spans 15 days
Delta
Delta
MDW
12:00a
SJU
6:11a
6h 11m
1 stop
SJU
12:00a
MDW
8:05a
8h 05m
1 stop
Depart: Wed Dec 6 2017 Return: Tue Dec 12 2017 Trip spans 7 days
Multiple Airlines
Multiple Airlines
MDW
12:00a
SJU
4:11p
16h 11m
2 stops
SJU
12:00a
MDW
4:57p
16h 57m
2 stops
Depart: Thu Jan 18 2018 Return: Mon Jan 22 2018 Trip spans 5 days
Delta
Delta
MDW
12:00a
SJU
6:22a
6h 22m
1 stop
SJU
12:00a
MDW
7:53a
7h 53m
1 stop
Depart: Thu Jan 25 2018 Return: Tue Jan 30 2018 Trip spans 6 days
Delta
Delta
MDW
12:00a
SJU
6:22a
6h 22m
1 stop
SJU
12:00a
MDW
7:53a
7h 53m
1 stop
Depart: Thu Feb 8 2018 Return: Tue Feb 20 2018 Trip spans 13 days
Delta
Delta
MDW
12:00a
SJU
7:52a
7h 52m
1 stop
SJU
12:00a
MDW
6:45a
6h 45m
1 stop
Depart: Mon Feb 12 2018 Return: Wed Feb 14 2018 Trip spans 3 days
Delta
Delta
MDW
12:00a
SJU
6:22a
6h 22m
1 stop
SJU
12:00a
MDW
7:53a
7h 53m
1 stop
Depart: Fri Dec 8 2017 Return: Mon Dec 18 2017 Trip spans 11 days
Delta
Delta
MDW
12:00a
SJU
7:50a
7h 50m
1 stop
SJU
12:00a
MDW
6:45a
6h 45m
1 stop
Depart: Tue Mar 6 2018 Return: Fri Mar 9 2018 Trip spans 4 days
Delta
Delta
MDW
12:00a
SJU
6:22a
6h 22m
1 stop
SJU
12:00a
MDW
8:03a
8h 03m
1 stop
Depart: Wed Mar 7 2018 Return: Wed Mar 14 2018 Trip spans 7 days
Delta
Delta
MDW
12:00a
SJU
6:32a
6h 32m
1 stop
SJU
12:00a
MDW
9:38a
9h 38m
1 stop
Depart: Mon Nov 6 2017 Return: Mon Nov 13 2017 Trip spans 8 days
Delta
Delta
MDW
12:00a
SJU
7:53a
7h 53m
1 stop
SJU
12:00a
MDW
8:05a
8h 05m
1 stop
Depart: Tue Oct 24 2017 Return: Mon Oct 30 2017 Trip spans 7 days
Multiple Airlines
Multiple Airlines
MDW
12:00a
SJU
4:29p
16h 29m
2 stops
SJU
12:00a
MDW
8:25p
20h 25m
2 stops
Depart: Mon Apr 16 2018 Return: Fri Apr 20 2018 Trip spans 5 days
Delta
Delta
MDW
12:00a
SJU
6:22a
6h 22m
1 stop
SJU
12:00a
MDW
9:38a
9h 38m
1 stop
Depart: Sat Dec 2 2017 Return: Sat Dec 9 2017 Trip spans 8 days
Delta
Delta
MDW
12:00a
SJU
7:48a
7h 48m
1 stop
SJU
12:00a
MDW
6:45a
6h 45m
1 stop
Depart: Mon Dec 25 2017 Return: Thu Jan 4 2018 Trip spans 11 days
Delta
Delta
MDW
12:00a
SJU
7:52a
7h 52m
1 stop
SJU
12:00a
MDW
7:53a
7h 53m
1 stop
Depart: Sat Dec 16 2017 Return: Tue Dec 26 2017 Trip spans 11 days
Delta
Delta
MDW
12:00a
SJU
7:48a
7h 48m
1 stop
SJU
12:00a
MDW
8:53a
8h 53m
1 stop
Depart: Thu Mar 1 2018 Return: Sun Mar 11 2018 Trip spans 11 days
Delta
Delta
MDW
12:00a
SJU
7:52a
7h 52m
1 stop
SJU
12:00a
MDW
8:32a
7h 32m
1 stop
Depart: Sat Mar 10 2018 Return: Sun Mar 18 2018 Trip spans 8 days
$1060
Select
Delta
Delta
MDW
12:00a
SJU
6:32a
6h 32m
1 stop
SJU
12:00a
MDW
9:38a
9h 38m
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.

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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

Chicago
$302
Destination

San Juan
$302
Airlines