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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago Midway to Puerto Rico

(Round-trip)
Depart: Fri Jun 23 2017 Return: Sat Jun 24 2017 Trip spans 2 days
Delta
Delta
MDW
12:00a
SJU
6:26a
6h 26m
1 stop
SJU
12:00a
MDW
8:28a
8h 28m
1 stop
Depart: Sat Jun 24 2017 Return: Mon Jun 26 2017 Trip spans 3 days
Delta
Delta
MDW
12:00a
SJU
7:29a
7h 29m
1 stop
SJU
12:00a
MDW
7:42a
7h 42m
1 stop
Depart: Sat Jun 24 2017 Return: Sun Jun 25 2017 Trip spans 2 days
$1165
Select
Multiple Airlines
Multiple Airlines
MDW
12:00a
SJU
12:59p
12h 59m
2 stops
SJU
12:00a
MDW
2:17p
14h 17m
2 stops
Depart: Mon Jun 26 2017 Return: Sun Jul 2 2017 Trip spans 7 days
Delta
Delta
MDW
12:00a
SJU
9:04a
9h 04m
1 stop
SJU
12:00a
MDW
8:45a
8h 45m
1 stop
Depart: Tue Jun 27 2017 Return: Sun Jul 2 2017 Trip spans 6 days
Delta
Delta
MDW
12:00a
SJU
6:26a
6h 26m
1 stop
SJU
12:00a
MDW
9:32a
9h 32m
1 stop
Depart: Fri Jun 23 2017 Return: Thu Jul 6 2017 Trip spans 14 days
Delta
Delta
MDW
12:00a
SJU
6:26a
6h 26m
1 stop
SJU
12:00a
MDW
10:01a
10h 01m
2 stops
Depart: Sat Jun 24 2017 Return: Thu Jul 6 2017 Trip spans 13 days
Delta
Delta
MDW
12:00a
SJU
8:49a
8h 49m
1 stop
SJU
12:00a
MDW
10:01a
10h 01m
2 stops
Depart: Mon Jun 26 2017 Return: Thu Jul 6 2017 Trip spans 11 days
Delta
Delta
MDW
12:00a
SJU
9:04a
9h 04m
1 stop
SJU
12:00a
MDW
10:01a
10h 01m
2 stops
Depart: Tue Jun 27 2017 Return: Thu Jul 6 2017 Trip spans 10 days
Delta
Delta
MDW
12:00a
SJU
6:26a
6h 26m
1 stop
SJU
12:00a
MDW
10:01a
10h 01m
2 stops
Depart: Fri Jun 23 2017 Return: Wed Jun 28 2017 Trip spans 6 days
Delta
Delta
MDW
12:00a
SJU
6:26a
6h 26m
1 stop
SJU
12:00a
MDW
9:41a
9h 41m
1 stop
Depart: Sat Jun 24 2017 Return: Wed Jun 28 2017 Trip spans 5 days
Delta
Delta
MDW
12:00a
SJU
7:29a
7h 29m
1 stop
SJU
12:00a
MDW
9:41a
9h 41m
1 stop
Depart: Mon Jun 26 2017 Return: Wed Jun 28 2017 Trip spans 3 days
Delta
Delta
MDW
12:00a
SJU
9:04a
9h 04m
1 stop
SJU
12:00a
MDW
9:41a
9h 41m
1 stop
Depart: Tue Jun 27 2017 Return: Wed Jun 28 2017 Trip spans 2 days
Delta
Delta
MDW
12:00a
SJU
6:26a
6h 26m
1 stop
SJU
12:00a
MDW
9:41a
9h 41m
1 stop
Depart: Sat Jun 24 2017 Return: Tue Jul 11 2017 Trip spans 18 days
Delta
Delta
MDW
12:00a
SJU
7:29a
7h 29m
1 stop
SJU
12:00a
MDW
6:41a
6h 41m
1 stop
Depart: Sun Jun 25 2017 Return: Tue Jun 27 2017 Trip spans 3 days
Delta
Delta
MDW
12:00a
SJU
2:31p
14h 31m
2 stops
SJU
12:00a
MDW
9:41a
9h 41m
1 stop
Depart: Mon Jun 26 2017 Return: Mon Jul 3 2017 Trip spans 8 days
Delta
Delta
MDW
12:00a
SJU
9:04a
9h 04m
1 stop
SJU
12:00a
MDW
9:07a
9h 07m
1 stop
Depart: Tue Jun 27 2017 Return: Wed Jul 5 2017 Trip spans 9 days
Delta
Delta
MDW
12:00a
SJU
7:34a
7h 34m
1 stop
SJU
12:00a
MDW
6:41a
6h 41m
1 stop
Depart: Sun Jun 25 2017 Return: Sun Jul 2 2017 Trip spans 8 days
Delta
Delta
MDW
12:00a
SJU
1:31p
13h 31m
2 stops
SJU
12:00a
MDW
7:43a
7h 43m
1 stop
Depart: Sun Jun 25 2017 Return: Thu Jul 6 2017 Trip spans 12 days
Delta
Delta
MDW
12:00a
SJU
5:41p
17h 41m
2 stops
SJU
12:00a
MDW
10:01a
10h 01m
2 stops
Depart: Mon Jun 26 2017 Return: Tue Jul 11 2017 Trip spans 16 days
Delta
Delta
MDW
12:00a
SJU
9:04a
9h 04m
1 stop
SJU
12:00a
MDW
8:30a
8h 30m
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
$562
Destination

San Juan
$562
Airlines