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
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: Wed May 10 2017 Return: Fri May 12 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
ORD
1:17p
BQN
9:16p
7h 59m
1 stop
BQN
11:16p
ORD
7:46a
8h 30m
1 stop
Depart: Wed Sep 6 2017 Return: Sat Sep 9 2017 Trip spans 4 days
Major Airline
Major Airline
ORD
10:50p
SJU
11:14a
12h 24m
1 stop
SJU
1:46a
ORD
3:40p
13h 54m
1 stop
Depart: Wed May 17 2017 Return: Tue May 30 2017 Trip spans 14 days
JetBlue
JetBlue
ORD
2:19a
BQN
9:19p
19h 00m
1 stop
BQN
11:30p
ORD
7:18p
19h 48m
1 stop
Depart: Sun Sep 3 2017 Return: Wed Sep 6 2017 Trip spans 4 days
American Airlines
American Airlines
ORD
5:05a
SJU
10:00a
4h 55m
nonstop
SJU
10:55a
ORD
3:57p
5h 02m
nonstop
Depart: Fri Jun 9 2017 Return: Sat Jun 10 2017 Trip spans 2 days
United
United
ORD
3:30p
SJU
8:15p
4h 45m
nonstop
SJU
10:10p
ORD
3:20a
5h 10m
nonstop
Depart: Sat May 13 2017 Return: Mon May 15 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
ORD
1:17p
BQN
9:16p
7h 59m
1 stop
BQN
11:16p
ORD
7:46a
8h 30m
1 stop
Depart: Tue Sep 12 2017 Return: Wed Sep 27 2017 Trip spans 16 days
Major Airline
Major Airline
ORD
9:15p
SJU
4:06a
6h 51m
2 stops
SJU
9:00a
ORD
3:40p
6h 40m
2 stops
Depart: Wed Sep 20 2017 Return: Fri Sep 22 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
ORD
1:23p
BQN
9:11p
7h 48m
1 stop
BQN
11:11p
ORD
6:53a
7h 42m
1 stop
Depart: Sat Sep 2 2017 Return: Wed Sep 6 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
9:55a
SJU
6:36p
8h 41m
1 stop
SJU
4:36a
ORD
3:40p
11h 04m
1 stop
Depart: Tue Apr 18 2017 Return: Tue Apr 25 2017 Trip spans 8 days
JetBlue
JetBlue
ORD
3:00a
SJU
7:27a
28h 27m
1 stop
SJU
5:08p
ORD
8:10p
27h 02m
1 stop
Depart: Fri May 5 2017 Return: Tue May 9 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
5:40a
SJU
10:14a
4h 34m
nonstop
SJU
12:15p
ORD
5:35p
5h 20m
nonstop
Depart: Tue Jun 13 2017 Return: Thu Jun 22 2017 Trip spans 10 days
United
United
ORD
2:00a
SJU
10:28a
8h 28m
1 stop
SJU
10:25a
ORD
3:35p
5h 10m
nonstop
Depart: Mon May 1 2017 Return: Fri May 5 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
1:15a
SJU
8:05a
6h 50m
1 stop
SJU
12:17p
ORD
8:59p
8h 42m
1 stop
Depart: Thu Aug 31 2017 Return: Wed Sep 6 2017 Trip spans 7 days
American Airlines
American Airlines
ORD
5:05a
SJU
10:00a
4h 55m
nonstop
SJU
10:55a
ORD
3:57p
5h 02m
nonstop
Depart: Mon Apr 3 2017 Return: Mon Apr 10 2017 Trip spans 8 days
JetBlue
JetBlue
ORD
9:25a
SJU
10:45p
13h 20m
1 stop
SJU
11:00p
ORD
9:48a
10h 48m
1 stop
Depart: Fri Jun 16 2017 Return: Tue Jun 20 2017 Trip spans 5 days
United
United
ORD
3:30p
SJU
8:15p
4h 45m
nonstop
SJU
12:23p
ORD
8:18p
7h 55m
1 stop
Depart: Thu Apr 20 2017 Return: Tue Apr 25 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
2:40a
SJU
6:40a
28h 00m
2 stops
SJU
1:08p
ORD
4:10p
27h 02m
2 stops
Depart: Tue May 2 2017 Return: Fri May 5 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
1:15a
SJU
8:05a
6h 50m
1 stop
SJU
12:17p
ORD
8:59p
8h 42m
1 stop
Depart: Mon Sep 4 2017 Return: Wed Sep 6 2017 Trip spans 3 days
American Airlines
American Airlines
ORD
5:05a
SJU
10:00a
4h 55m
nonstop
SJU
10:55a
ORD
3:57p
5h 02m
nonstop
Depart: Wed Aug 9 2017 Return: Tue Aug 22 2017 Trip spans 14 days
JetBlue
JetBlue
ORD
3:00a
SJU
12:07p
9h 07m
1 stop
SJU
12:59p
ORD
7:42p
6h 43m
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.

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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,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Chicago
$327
Destination

Aguadilla
$327
San Juan
$330