Find Cheap Flights from Chicago 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 to Puerto Rico

(Round-trip)
Depart: Tue Oct 17 2017 Return: Tue Nov 14 2017 Trip spans 29 days
Frontier
Frontier
ORD
SJU
19h 11m
1 stop
SJU
ORD
11h 23m
1 stop
Depart: Wed Oct 18 2017 Return: Mon Oct 30 2017 Trip spans 13 days
Spirit Airlines
Spirit Airlines
ORD
BQN
7h 33m
1 stop
BQN
ORD
7h 50m
1 stop
Depart: Thu Sep 21 2017 Return: Sun Sep 24 2017 Trip spans 4 days
American Airlines
American Airlines
ORD
SJU
4h 42m
nonstop
SJU
ORD
5h 17m
nonstop
Depart: Tue Oct 24 2017 Return: Tue Oct 31 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
ORD
SJU
14h 59m
1 stop
SJU
ORD
13h 31m
1 stop
Depart: Wed Nov 1 2017 Return: Tue Nov 7 2017 Trip spans 7 days
Frontier
Frontier
ORD
SJU
19h 07m
1 stop
SJU
ORD
11h 23m
1 stop
Depart: Wed Nov 1 2017 Return: Tue Nov 7 2017 Trip spans 7 days
Frontier
Frontier
ORD
SJU
19h 07m
1 stop
SJU
ORD
11h 23m
1 stop
Depart: Tue Oct 10 2017 Return: Mon Oct 16 2017 Trip spans 7 days
Frontier
Frontier
ORD
SJU
19h 11m
1 stop
SJU
ORD
11h 14m
1 stop
Depart: Sat Oct 21 2017 Return: Mon Oct 30 2017 Trip spans 10 days
Spirit Airlines
Spirit Airlines
ORD
BQN
7h 33m
1 stop
BQN
ORD
7h 50m
1 stop
Depart: Fri Sep 22 2017 Return: Sun Sep 24 2017 Trip spans 3 days
American Airlines
American Airlines
ORD
SJU
4h 42m
nonstop
SJU
ORD
5h 17m
nonstop
Depart: Tue Oct 17 2017 Return: Mon Oct 23 2017 Trip spans 7 days
Frontier
Frontier
ORD
SJU
19h 11m
1 stop
SJU
ORD
11h 14m
1 stop
Depart: Sat Sep 30 2017 Return: Mon Oct 9 2017 Trip spans 10 days
Spirit Airlines
Spirit Airlines
ORD
BQN
7h 33m
1 stop
BQN
ORD
7h 50m
1 stop
Depart: Fri Sep 22 2017 Return: Sun Sep 24 2017 Trip spans 3 days
American Airlines
American Airlines
ORD
SJU
4h 42m
nonstop
SJU
ORD
5h 17m
nonstop
Depart: Wed Oct 18 2017 Return: Tue Oct 24 2017 Trip spans 7 days
Frontier
Frontier
ORD
SJU
19h 11m
1 stop
SJU
ORD
11h 14m
1 stop
Depart: Wed Nov 1 2017 Return: Wed Nov 8 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
ORD
SJU
12h 32m
1 stop
SJU
ORD
8h 19m
1 stop
Depart: Sat Sep 30 2017 Return: Fri Oct 6 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
BQN
7h 33m
1 stop
BQN
ORD
7h 50m
1 stop
Depart: Sat Sep 23 2017 Return: Sun Sep 24 2017 Trip spans 2 days
American Airlines
American Airlines
ORD
SJU
4h 42m
nonstop
SJU
ORD
5h 17m
nonstop
Depart: Thu Oct 19 2017 Return: Wed Oct 25 2017 Trip spans 7 days
Frontier
Frontier
ORD
SJU
19h 11m
1 stop
SJU
ORD
11h 14m
1 stop
Depart: Wed Oct 11 2017 Return: Sat Oct 14 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
ORD
SJU
6h 56m
1 stop
SJU
ORD
14h 03m
1 stop
Depart: Fri Sep 22 2017 Return: Sat Sep 23 2017 Trip spans 2 days
American Airlines
American Airlines
ORD
SJU
10h 44m
2 stops
SJU
ORD
8h 54m
1 stop
Depart: Wed Oct 18 2017 Return: Wed Oct 25 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
BQN
7h 33m
1 stop
BQN
ORD
7h 50m
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
$195
Destination

Aguadilla
$246
San Juan
$195