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
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: Wed Mar 15 2017 Return: Thu Mar 23 2017 Trip spans 9 days
Delta
Delta
MDW
7:55a
SJU
4:39p
8h 44m
1 stop
SJU
10:15a
MDW
5:15p
7h 00m
1 stop
Depart: Mon Mar 20 2017 Return: Wed Mar 22 2017 Trip spans 3 days
Delta
Delta
MDW
9:48a
SJU
4:39p
6h 51m
1 stop
SJU
3:05a
MDW
12:12p
9h 07m
1 stop
Depart: Tue Mar 21 2017 Return: Wed Mar 22 2017 Trip spans 2 days
Delta
Delta
MDW
2:00a
SJU
9:45a
7h 45m
1 stop
SJU
11:40a
MDW
7:10p
7h 30m
1 stop
Depart: Wed Mar 22 2017 Return: Thu Mar 23 2017 Trip spans 2 days
Delta
Delta
MDW
2:00a
SJU
8:18a
6h 18m
1 stop
SJU
10:15a
MDW
5:15p
7h 00m
1 stop
Depart: Tue Mar 28 2017 Return: Tue May 9 2017 Trip spans 43 days
Delta
Delta
MDW
9:48a
SJU
4:39p
6h 51m
1 stop
SJU
11:50a
MDW
7:09p
7h 19m
1 stop
Depart: Wed Mar 29 2017 Return: Wed Apr 5 2017 Trip spans 8 days
Delta
Delta
MDW
2:30a
SJU
10:05a
7h 35m
1 stop
SJU
3:15a
MDW
10:33a
7h 18m
1 stop
Depart: Thu Mar 30 2017 Return: Wed Apr 5 2017 Trip spans 7 days
Delta
Delta
MDW
2:30a
SJU
10:05a
7h 35m
1 stop
SJU
3:15a
MDW
12:17p
9h 02m
1 stop
Depart: Mon Apr 3 2017 Return: Wed Apr 5 2017 Trip spans 3 days
Delta
Delta
MDW
3:20a
SJU
9:50a
6h 30m
1 stop
SJU
3:15a
MDW
12:17p
9h 02m
1 stop
Depart: Tue Apr 4 2017 Return: Wed Apr 12 2017 Trip spans 9 days
Delta
Delta
MDW
8:24a
SJU
4:33p
8h 09m
1 stop
SJU
11:45a
MDW
7:25p
7h 40m
1 stop
Depart: Wed Apr 5 2017 Return: Wed Apr 12 2017 Trip spans 8 days
Delta
Delta
MDW
8:24a
SJU
4:33p
8h 09m
1 stop
SJU
11:45a
MDW
7:25p
7h 40m
1 stop
Depart: Tue Apr 11 2017 Return: Wed Apr 12 2017 Trip spans 2 days
Delta
Delta
MDW
2:00a
SJU
9:50a
7h 50m
1 stop
SJU
11:45a
MDW
7:25p
7h 40m
1 stop
Depart: Wed Apr 12 2017 Return: Tue Apr 18 2017 Trip spans 7 days
Delta
Delta
MDW
10:08a
SJU
4:33p
6h 25m
1 stop
SJU
3:15a
MDW
12:17p
9h 02m
1 stop
Depart: Tue Apr 18 2017 Return: Wed Apr 19 2017 Trip spans 2 days
Delta
Delta
MDW
3:20a
SJU
9:50a
6h 30m
1 stop
SJU
11:45a
MDW
7:25p
7h 40m
1 stop
Depart: Sun Apr 23 2017 Return: Wed Apr 26 2017 Trip spans 4 days
Delta
Delta
MDW
10:08a
SJU
4:33p
6h 25m
1 stop
SJU
3:15a
MDW
12:17p
9h 02m
1 stop
Depart: Mon Apr 24 2017 Return: Thu Apr 27 2017 Trip spans 4 days
Delta
Delta
MDW
10:08a
SJU
4:33p
6h 25m
1 stop
SJU
3:15a
MDW
12:17p
9h 02m
1 stop
Depart: Tue Apr 25 2017 Return: Tue May 2 2017 Trip spans 8 days
Delta
Delta
MDW
8:24a
SJU
4:33p
8h 09m
1 stop
SJU
3:25a
MDW
10:23a
6h 58m
1 stop
Depart: Wed Apr 26 2017 Return: Tue May 2 2017 Trip spans 7 days
Delta
Delta
MDW
3:20a
SJU
9:50a
6h 30m
1 stop
SJU
10:14a
MDW
7:09p
8h 55m
1 stop
Depart: Thu Apr 27 2017 Return: Tue May 2 2017 Trip spans 6 days
Delta
Delta
MDW
8:24a
SJU
4:33p
8h 09m
1 stop
SJU
10:14a
MDW
5:01p
6h 47m
1 stop
Depart: Fri Apr 28 2017 Return: Tue May 2 2017 Trip spans 5 days
Delta
Delta
MDW
8:24a
SJU
4:33p
8h 09m
1 stop
SJU
10:14a
MDW
5:01p
6h 47m
1 stop
Depart: Sat Apr 29 2017 Return: Wed May 3 2017 Trip spans 5 days
Delta
Delta
MDW
8:40a
SJU
4:30p
7h 50m
1 stop
SJU
11:50a
MDW
7:09p
7h 19m
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
$362
Destination

San Juan
$362
Airlines