Find Deals on Flights from Chicago O'Hare International 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 O'Hare International to Puerto Rico

(Round-trip)
Depart: Tue Feb 7 2017 Return: Fri Feb 10 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
12:15a
SJU
7:08a
6h 53m
1 stop
SJU
12:28p
ORD
7:59p
7h 31m
1 stop
Depart: Sun Mar 5 2017 Return: Mon Mar 13 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
11:35p
SJU
6:54a
7h 19m
2 stops
SJU
9:04p
ORD
5:49a
8h 45m
2 stops
Depart: Wed Mar 8 2017 Return: Tue Mar 14 2017 Trip spans 6 days
JetBlue
JetBlue
ORD
2:00a
SJU
10:27a
8h 27m
1 stop
SJU
4:59a
ORD
8:09p
15h 10m
1 stop
Depart: Tue Feb 14 2017 Return: Thu Feb 16 2017 Trip spans 3 days
American Airlines
American Airlines
ORD
3:35a
SJU
8:05a
4h 30m
nonstop
SJU
10:57a
ORD
4:24p
5h 27m
nonstop
Depart: Mon Mar 20 2017 Return: Wed Mar 22 2017 Trip spans 3 days
United
United
ORD
3:34a
SJU
7:59a
4h 25m
nonstop
SJU
10:05a
ORD
3:05p
5h 00m
nonstop
Depart: Mon Mar 13 2017 Return: Wed Mar 22 2017 Trip spans 10 days
Delta
Delta
ORD
8:15a
SJU
5:48p
9h 33m
1 stop
SJU
3:05a
ORD
9:54a
6h 49m
1 stop
Depart: Mon Feb 13 2017 Return: Tue Feb 14 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
12:15a
SJU
7:07a
6h 52m
1 stop
SJU
12:28p
ORD
7:59p
7h 31m
1 stop
Depart: Tue Feb 28 2017 Return: Tue Mar 7 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
12:15a
SJU
7:07a
6h 52m
1 stop
SJU
12:28p
ORD
7:59p
7h 31m
1 stop
Depart: Tue Mar 7 2017 Return: Tue Mar 14 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
12:15a
SJU
7:07a
6h 52m
1 stop
SJU
12:28p
ORD
7:59p
7h 31m
1 stop
Depart: Wed Feb 8 2017 Return: Tue Feb 14 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
12:15a
SJU
12:44p
12h 29m
1 stop
SJU
12:28p
ORD
8:29a
20h 01m
1 stop
Depart: Fri Mar 3 2017 Return: Sun Mar 5 2017 Trip spans 3 days
Major Airline
Major Airline
ORD
12:40a
SJU
8:50a
8h 10m
1 stop
SJU
5:00p
ORD
2:01a
9h 01m
1 stop
Depart: Wed May 10 2017 Return: Tue Jun 6 2017 Trip spans 28 days
JetBlue
JetBlue
ORD
2:19a
SJU
10:49a
8h 30m
1 stop
SJU
11:02p
ORD
6:54a
7h 52m
1 stop
Depart: Wed Feb 1 2017 Return: Fri Feb 10 2017 Trip spans 10 days
Spirit Airlines
Spirit Airlines
ORD
12:15a
SJU
7:08a
6h 53m
1 stop
SJU
12:28p
ORD
7:59p
7h 31m
1 stop
Depart: Mon Feb 27 2017 Return: Fri Mar 10 2017 Trip spans 12 days
Major Airline
Major Airline
ORD
9:00p
SJU
12:50p
15h 50m
nonstop
SJU
7:28a
ORD
2:59p
7h 31m
nonstop
Depart: Tue Mar 21 2017 Return: Thu Mar 23 2017 Trip spans 3 days
United
United
ORD
3:34a
SJU
7:59a
4h 25m
nonstop
SJU
10:05a
ORD
3:05p
5h 00m
nonstop
Depart: Sat Apr 29 2017 Return: Tue May 2 2017 Trip spans 4 days
American Airlines
American Airlines
ORD
12:55p
SJU
5:34p
4h 39m
nonstop
SJU
12:05p
ORD
5:25p
5h 20m
nonstop
Depart: Wed Apr 5 2017 Return: Wed Apr 26 2017 Trip spans 22 days
JetBlue
JetBlue
ORD
3:00a
SJU
11:28a
8h 28m
1 stop
SJU
10:21a
ORD
8:10p
9h 49m
1 stop
Depart: Thu Feb 2 2017 Return: Wed Feb 8 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
12:15a
SJU
7:08a
6h 53m
1 stop
SJU
12:41p
ORD
7:57p
7h 16m
1 stop
Depart: Tue Jul 25 2017 Return: Tue Aug 1 2017 Trip spans 8 days
Delta
Delta
ORD
2:00a
SJU
10:23a
8h 23m
1 stop
SJU
3:00a
ORD
1:05p
10h 05m
1 stop
Depart: Sat Apr 15 2017 Return: Thu Apr 27 2017 Trip spans 13 days
United
United
ORD
7:15p
SJU
12:00a
4h 45m
nonstop
SJU
10:22a
ORD
3:32p
5h 10m
nonstop
* 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
$169
Destination

San Juan
$169