Find Cheap 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 Oct 18 2017 Return: Fri Oct 20 2017 Trip spans 3 days
Frontier
Frontier
ORD
12:00a
SJU
7:11p
19h 11m
1 stop
SJU
12:00a
ORD
11:14a
11h 14m
1 stop
Depart: Wed Oct 18 2017 Return: Wed Nov 1 2017 Trip spans 15 days
Spirit Airlines
Spirit Airlines
ORD
12:00a
BQN
7:33a
7h 33m
1 stop
BQN
12:00a
ORD
7:50a
7h 50m
1 stop
Depart: Sun Sep 24 2017 Return: Wed Oct 11 2017 Trip spans 18 days
Multiple Airlines
Multiple Airlines
ORD
12:00a
SJU
4:42a
4h 42m
nonstop
SJU
12:00a
ORD
9:43a
9h 43m
1 stop
Depart: Fri Sep 29 2017 Return: Mon Oct 2 2017 Trip spans 4 days
JetBlue
JetBlue
ORD
12:00a
SJU
6:41a
6h 41m
1 stop
SJU
12:00a
ORD
9:43a
9h 43m
1 stop
Depart: Sun Oct 22 2017 Return: Fri Oct 27 2017 Trip spans 6 days
United
United
ORD
12:00a
SJU
4:40a
4h 40m
nonstop
SJU
12:00a
ORD
5:05a
5h 05m
nonstop
Depart: Mon Oct 9 2017 Return: Mon Oct 16 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
12:00a
SJU
4:42a
4h 42m
nonstop
SJU
12:00a
ORD
5:17a
5h 17m
nonstop
Depart: Wed Feb 21 2018 Return: Tue Feb 27 2018 Trip spans 7 days
Frontier
Frontier
ORD
12:00a
SJU
7:09p
19h 09m
1 stop
SJU
12:00a
ORD
11:36a
11h 36m
1 stop
Depart: Mon Sep 25 2017 Return: Fri Sep 29 2017 Trip spans 5 days
Delta
Delta
ORD
12:00a
SJU
9:02a
9h 02m
1 stop
SJU
12:00a
ORD
7:21a
7h 21m
1 stop
Depart: Sun Sep 24 2017 Return: Tue Sep 26 2017 Trip spans 3 days
Multiple Airlines
Multiple Airlines
ORD
12:00a
SJU
7:49a
7h 49m
1 stop
SJU
12:00a
ORD
6:49a
6h 49m
1 stop
Depart: Wed Mar 14 2018 Return: Tue Mar 20 2018 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
12:00a
BQN
7:03a
7h 03m
1 stop
BQN
12:00a
ORD
8:43a
8h 43m
1 stop
Depart: Wed Jan 17 2018 Return: Tue Jan 23 2018 Trip spans 7 days
Frontier
Frontier
ORD
12:00a
SJU
7:09p
19h 09m
1 stop
SJU
12:00a
ORD
11:36a
11h 36m
1 stop
Depart: Tue Dec 12 2017 Return: Sat Dec 16 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
ORD
12:00a
SJU
2:30p
14h 30m
1 stop
SJU
12:00a
ORD
8:28a
8h 28m
1 stop
Depart: Wed Nov 8 2017 Return: Tue Nov 14 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
12:00a
SJU
6:54a
6h 54m
1 stop
SJU
12:00a
ORD
8:28a
8h 28m
1 stop
Depart: Tue Feb 6 2018 Return: Thu Feb 15 2018 Trip spans 10 days
Frontier
Frontier
ORD
12:00a
SJU
7:09p
19h 09m
1 stop
SJU
12:00a
ORD
11:36a
11h 36m
1 stop
Depart: Mon Dec 11 2017 Return: Sat Dec 16 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
12:00a
SJU
6:56a
6h 56m
1 stop
SJU
12:00a
ORD
8:28a
8h 28m
1 stop
Depart: Sun Jan 21 2018 Return: Tue Jan 23 2018 Trip spans 3 days
Frontier
Frontier
ORD
12:00a
SJU
7:09p
19h 09m
1 stop
SJU
12:00a
ORD
11:36a
11h 36m
1 stop
Depart: Sun Nov 12 2017 Return: Thu Nov 16 2017 Trip spans 5 days
United
United
ORD
12:00a
SJU
4:35a
4h 35m
nonstop
SJU
12:00a
ORD
5:10a
5h 10m
nonstop
Depart: Sat Sep 30 2017 Return: Tue Oct 10 2017 Trip spans 11 days
Spirit Airlines
Spirit Airlines
ORD
12:00a
SJU
6:48p
18h 48m
1 stop
SJU
12:00a
ORD
8:35a
8h 35m
1 stop
Depart: Tue Feb 6 2018 Return: Mon Feb 12 2018 Trip spans 7 days
Frontier
Frontier
ORD
12:00a
SJU
2:30p
14h 30m
1 stop
SJU
12:00a
ORD
6:25p
18h 25m
1 stop
Depart: Thu Oct 26 2017 Return: Sat Oct 28 2017 Trip spans 3 days
United
United
ORD
12:00a
BQN
2:50p
14h 50m
1 stop
BQN
12:00a
ORD
9:04a
9h 04m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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Airports
Origin

Chicago
$206
Destination

Aguadilla
$252
San Juan
$206