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 Sep 19 2017 Return: Wed Sep 27 2017 Trip spans 9 days
Delta
Delta
MDW
12:00a
SJU
7:35a
7h 35m
1 stop
SJU
12:00a
MDW
10:50a
10h 50m
2 stops
Depart: Thu Sep 14 2017 Return: Mon Sep 18 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
MDW
12:00a
SJU
8:51p
20h 51m
2 stops
SJU
12:00a
MDW
6:50p
18h 50m
2 stops
Depart: Fri Sep 8 2017 Return: Wed Sep 13 2017 Trip spans 6 days
Delta
Delta
MDW
12:00a
SJU
6:44a
6h 44m
1 stop
SJU
12:00a
MDW
9:35a
9h 35m
1 stop
Depart: Tue Sep 19 2017 Return: Sat Sep 30 2017 Trip spans 12 days
Delta
Delta
MDW
12:00a
SJU
6:23a
6h 23m
1 stop
SJU
12:00a
MDW
9:23a
9h 23m
1 stop
Depart: Tue Oct 3 2017 Return: Wed Oct 11 2017 Trip spans 9 days
Delta
Delta
MDW
12:00a
SJU
6:11a
6h 11m
1 stop
SJU
12:00a
MDW
8:14a
8h 14m
1 stop
Depart: Tue Oct 10 2017 Return: Fri Nov 24 2017 Trip spans 46 days
Multiple Airlines
Multiple Airlines
MDW
12:00a
SJU
7:38a
7h 38m
1 stop
SJU
12:00a
MDW
4:46p
16h 46m
2 stops
Depart: Mon Oct 9 2017 Return: Sat Oct 14 2017 Trip spans 6 days
Delta
Delta
MDW
12:00a
SJU
6:24a
6h 24m
1 stop
SJU
12:00a
MDW
12:56p
12h 56m
2 stops
Depart: Tue Sep 12 2017 Return: Sat Sep 23 2017 Trip spans 12 days
Delta
Delta
MDW
12:00a
SJU
6:10a
6h 10m
1 stop
SJU
12:00a
MDW
9:23a
9h 23m
1 stop
Depart: Tue Sep 19 2017 Return: Tue Sep 26 2017 Trip spans 8 days
Delta
Delta
MDW
12:00a
SJU
7:35a
7h 35m
1 stop
SJU
12:00a
MDW
8:25a
8h 25m
1 stop
Depart: Fri Aug 25 2017 Return: Thu Aug 31 2017 Trip spans 7 days
Multiple Airlines
Multiple Airlines
MDW
12:00a
SJU
4:51a
28h 51m
2 stops
SJU
12:00a
MDW
7:44p
19h 44m
2 stops
Depart: Wed Sep 20 2017 Return: Sat Sep 23 2017 Trip spans 4 days
Delta
Delta
MDW
12:00a
SJU
6:10a
6h 10m
1 stop
SJU
12:00a
MDW
9:23a
9h 23m
1 stop
Depart: Fri Oct 6 2017 Return: Sun Oct 8 2017 Trip spans 3 days
Multiple Airlines
Multiple Airlines
MDW
12:00a
SJU
7:31p
19h 31m
2 stops
SJU
12:00a
MDW
9:25p
21h 25m
2 stops
Depart: Tue Oct 3 2017 Return: Tue Oct 10 2017 Trip spans 8 days
Delta
Delta
MDW
12:00a
SJU
8:36a
8h 36m
1 stop
SJU
12:00a
MDW
7:15a
7h 15m
1 stop
Depart: Fri Oct 6 2017 Return: Sun Oct 8 2017 Trip spans 3 days
Multiple Airlines
Multiple Airlines
MDW
12:00a
SJU
7:11p
43h 11m
3 stops
SJU
12:00a
MDW
9:25p
21h 25m
2 stops
Depart: Wed Oct 4 2017 Return: Thu Oct 12 2017 Trip spans 9 days
Delta
Delta
MDW
12:00a
SJU
6:24a
6h 24m
1 stop
SJU
12:00a
MDW
8:14a
8h 14m
1 stop
Depart: Fri Sep 15 2017 Return: Sat Sep 23 2017 Trip spans 9 days
Delta
Delta
MDW
12:00a
SJU
6:23a
6h 23m
1 stop
SJU
12:00a
MDW
9:23a
9h 23m
1 stop
Depart: Fri Sep 29 2017 Return: Mon Oct 2 2017 Trip spans 4 days
Delta
Delta
MDW
12:00a
SJU
6:23a
6h 23m
1 stop
SJU
12:00a
MDW
9:20a
9h 20m
1 stop
Depart: Mon Oct 9 2017 Return: Fri Oct 20 2017 Trip spans 12 days
Delta
Delta
MDW
12:00a
SJU
6:24a
6h 24m
1 stop
SJU
12:00a
MDW
9:20a
9h 20m
1 stop
Depart: Fri Sep 1 2017 Return: Sun Sep 3 2017 Trip spans 3 days
Multiple Airlines
Multiple Airlines
MDW
12:00a
SJU
5:20p
17h 20m
2 stops
SJU
12:00a
MDW
5:25p
17h 25m
2 stops
Depart: Sat Oct 7 2017 Return: Sat Oct 14 2017 Trip spans 8 days
Delta
Delta
MDW
12:00a
SJU
6:39a
6h 39m
1 stop
SJU
12:00a
MDW
12:56p
12h 56m
2 stops
* 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,
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Airports
Origin

Chicago
$389
Destination

San Juan
$389
Airlines