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 Aug 16 2017 Return: Mon Aug 28 2017 Trip spans 13 days
Frontier
Frontier
ORD
2:00a
SJU
7:40p
17h 40m
1 stop
SJU
11:05p
ORD
4:42p
17h 37m
1 stop
Depart: Sat Nov 4 2017 Return: Sun Nov 5 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
1:23p
BQN
8:56p
7h 33m
1 stop
BQN
11:26p
ORD
6:49a
7h 23m
1 stop
Depart: Tue Nov 21 2017 Return: Wed Nov 22 2017 Trip spans 2 days
JetBlue
JetBlue
ORD
2:00a
SJU
11:56a
9h 56m
1 stop
SJU
9:25a
ORD
8:07p
10h 42m
1 stop
Depart: Sun Dec 31 2017 Return: Wed Jan 24 2018 Trip spans 25 days
United
United
ORD
10:50a
SJU
9:49p
10h 59m
1 stop
SJU
10:10a
ORD
3:20p
5h 10m
nonstop
Depart: Tue Jan 2 2018 Return: Sat Jan 20 2018 Trip spans 19 days
Delta
Delta
ORD
1:00a
SJU
7:22a
6h 22m
1 stop
SJU
3:00a
ORD
11:02a
8h 02m
1 stop
Depart: Sat Aug 19 2017 Return: Mon Aug 28 2017 Trip spans 10 days
Frontier
Frontier
ORD
2:00a
SJU
7:40p
17h 40m
1 stop
SJU
11:05p
ORD
4:42p
17h 37m
1 stop
Depart: Tue Dec 19 2017 Return: Fri Dec 22 2017 Trip spans 4 days
American Airlines
American Airlines
ORD
9:00a
SJU
5:59p
8h 59m
2 stops
SJU
1:40p
ORD
10:29p
8h 49m
1 stop
Depart: Tue Aug 22 2017 Return: Mon Aug 28 2017 Trip spans 7 days
Frontier
Frontier
ORD
2:00a
SJU
7:40p
17h 40m
1 stop
SJU
11:05p
ORD
4:42p
17h 37m
1 stop
Depart: Sun Oct 1 2017 Return: Wed Oct 4 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
1:15a
SJU
8:11a
6h 56m
1 stop
SJU
10:12a
ORD
4:55p
6h 43m
1 stop
Depart: Wed Aug 23 2017 Return: Mon Aug 28 2017 Trip spans 6 days
Frontier
Frontier
ORD
2:00a
SJU
7:40p
17h 40m
1 stop
SJU
11:05p
ORD
4:42p
17h 37m
1 stop
Depart: Mon Oct 2 2017 Return: Sat Oct 7 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
6:27a
SJU
3:37p
9h 10m
1 stop
SJU
12:23p
ORD
8:58p
8h 35m
1 stop
Depart: Mon Nov 20 2017 Return: Thu Nov 30 2017 Trip spans 11 days
JetBlue
JetBlue
ORD
2:00a
SJU
11:56a
9h 56m
1 stop
SJU
1:21p
ORD
8:07p
6h 46m
nonstop
Depart: Sat Aug 26 2017 Return: Mon Aug 28 2017 Trip spans 3 days
Frontier
Frontier
ORD
2:00a
SJU
7:40p
17h 40m
1 stop
SJU
11:05p
ORD
4:42p
17h 37m
1 stop
Depart: Wed Jan 3 2018 Return: Sat Jan 20 2018 Trip spans 18 days
Delta
Delta
ORD
6:00a
SJU
3:34p
9h 34m
1 stop
SJU
3:00a
ORD
11:02a
8h 02m
1 stop
Depart: Mon Oct 9 2017 Return: Fri Oct 13 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
6:27a
SJU
3:37p
9h 10m
1 stop
SJU
12:23p
ORD
8:58p
8h 35m
1 stop
Depart: Wed Nov 22 2017 Return: Tue Dec 5 2017 Trip spans 14 days
JetBlue
JetBlue
ORD
2:00a
SJU
11:56a
9h 56m
1 stop
SJU
1:21p
ORD
8:07p
6h 46m
nonstop
Depart: Fri Dec 8 2017 Return: Fri Dec 15 2017 Trip spans 8 days
United
United
ORD
4:00p
SJU
4:54a
12h 54m
1 stop
SJU
10:10a
ORD
3:20p
5h 10m
nonstop
Depart: Tue Aug 29 2017 Return: Tue Sep 5 2017 Trip spans 8 days
Frontier
Frontier
ORD
2:00a
SJU
7:40p
17h 40m
1 stop
SJU
11:05p
ORD
4:42p
17h 37m
1 stop
Depart: Tue Jan 9 2018 Return: Sat Jan 20 2018 Trip spans 12 days
Delta
Delta
ORD
6:00a
SJU
3:34p
9h 34m
1 stop
SJU
3:00a
ORD
11:02a
8h 02m
1 stop
Depart: Fri Oct 13 2017 Return: Mon Oct 16 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
1:15a
SJU
8:11a
6h 56m
1 stop
SJU
12:23p
ORD
8:58p
8h 35m
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.

If you have more questions or if you have a bad price to report to us,
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Airports
Origin

Chicago
$279
Destination

Aguadilla
$291
San Juan
$279