Find Deals on 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
Students
under 26
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: Sat Dec 31 2016 Return: Tue Jan 24 2017 Trip spans 25 days
Delta
Delta
MDW
10:26a
SJU
5:03p
6h 37m
1 stop
SJU
11:45a
MDW
7:46p
8h 01m
1 stop
Depart: Tue Jan 10 2017 Return: Tue Jan 24 2017 Trip spans 15 days
Delta
Delta
MDW
7:20a
SJU
3:37p
8h 17m
1 stop
SJU
11:45a
MDW
7:46p
8h 01m
1 stop
Depart: Thu Jan 12 2017 Return: Wed Jan 18 2017 Trip spans 7 days
Delta
Delta
MDW
9:08a
SJU
3:37p
6h 29m
1 stop
SJU
10:21a
MDW
7:46p
9h 25m
1 stop
Depart: Sun Jan 15 2017 Return: Thu Jan 19 2017 Trip spans 5 days
Delta
Delta
MDW
2:10a
SJU
8:48a
6h 38m
1 stop
SJU
11:45a
MDW
7:46p
8h 01m
1 stop
Depart: Mon Dec 26 2016 Return: Thu Jan 5 2017 Trip spans 11 days
Major Airline
Major Airline
MDW
12:00a
SJU
2:06a
2h 06m
nonstop
SJU
12:00a
MDW
6:06a
6h 06m
nonstop
Depart: Mon Jan 16 2017 Return: Tue Jan 24 2017 Trip spans 9 days
Delta
Delta
MDW
7:20a
SJU
3:37p
8h 17m
1 stop
SJU
11:45a
MDW
7:46p
8h 01m
1 stop
Depart: Tue Jan 17 2017 Return: Tue Jan 24 2017 Trip spans 8 days
Delta
Delta
MDW
9:08a
SJU
3:37p
6h 29m
1 stop
SJU
11:45a
MDW
7:46p
8h 01m
1 stop
Depart: Wed Jan 18 2017 Return: Tue Jan 24 2017 Trip spans 7 days
Delta
Delta
MDW
2:10a
SJU
8:49a
6h 39m
1 stop
SJU
11:45a
MDW
7:46p
8h 01m
1 stop
Depart: Thu Jan 19 2017 Return: Tue Jan 24 2017 Trip spans 6 days
Delta
Delta
MDW
7:20a
SJU
3:37p
8h 17m
1 stop
SJU
11:45a
MDW
7:46p
8h 01m
1 stop
Depart: Fri Jan 20 2017 Return: Tue Jan 24 2017 Trip spans 5 days
Delta
Delta
MDW
1:00a
SJU
8:49a
7h 49m
1 stop
SJU
11:45a
MDW
7:46p
8h 01m
1 stop
Depart: Sat Jan 21 2017 Return: Wed Jan 25 2017 Trip spans 5 days
Delta
Delta
MDW
8:45a
SJU
3:34p
6h 49m
1 stop
SJU
8:55a
MDW
5:02p
8h 07m
1 stop
Depart: Sun Jan 22 2017 Return: Fri Jan 27 2017 Trip spans 6 days
Delta
Delta
MDW
2:10a
SJU
8:49a
6h 39m
1 stop
SJU
10:21a
MDW
7:46p
9h 25m
1 stop
Depart: Mon Jan 23 2017 Return: Tue Feb 7 2017 Trip spans 16 days
Delta
Delta
MDW
1:00a
SJU
7:19a
6h 19m
1 stop
SJU
8:55a
MDW
5:02p
8h 07m
1 stop
Depart: Tue Jan 24 2017 Return: Tue Feb 7 2017 Trip spans 15 days
Delta
Delta
MDW
2:10a
SJU
8:49a
6h 39m
1 stop
SJU
11:45a
MDW
7:46p
8h 01m
1 stop
Depart: Wed Jan 25 2017 Return: Tue Feb 7 2017 Trip spans 14 days
Delta
Delta
MDW
9:08a
SJU
3:37p
6h 29m
1 stop
SJU
3:15a
MDW
10:33a
7h 18m
1 stop
Depart: Thu Jan 26 2017 Return: Tue Jan 31 2017 Trip spans 6 days
Delta
Delta
MDW
1:00a
SJU
7:19a
6h 19m
1 stop
SJU
10:21a
MDW
7:46p
9h 25m
1 stop
Depart: Fri Jan 27 2017 Return: Fri Feb 3 2017 Trip spans 8 days
Delta
Delta
MDW
7:20a
SJU
3:37p
8h 17m
1 stop
SJU
11:45a
MDW
7:46p
8h 01m
1 stop
Depart: Sat Jan 28 2017 Return: Wed Feb 1 2017 Trip spans 5 days
Delta
Delta
MDW
1:00a
SJU
7:17a
6h 17m
1 stop
SJU
3:15a
MDW
12:03p
8h 48m
1 stop
Depart: Sun Jan 29 2017 Return: Tue Feb 7 2017 Trip spans 10 days
Delta
Delta
MDW
9:08a
SJU
3:37p
6h 29m
1 stop
SJU
8:55a
MDW
5:02p
8h 07m
1 stop
Depart: Mon Jan 30 2017 Return: Tue Feb 7 2017 Trip spans 9 days
Delta
Delta
MDW
1:00a
SJU
7:19a
6h 19m
1 stop
SJU
11:45a
MDW
7:46p
8h 01m
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

Chicago
$307
Destination

San Juan
$307
Airlines