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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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago to Puerto Rico

(Round-trip)
Depart: Mon Sep 11 2017 Return: Sun Sep 17 2017 Trip spans 7 days
JetBlue
JetBlue
ORD
BQN
16h 58m
1 stop
BQN
ORD
21h 59m
1 stop
Depart: Wed Aug 30 2017 Return: Tue Sep 5 2017 Trip spans 7 days
Major Airline
Major Airline
ORD
BQN
11h 40m
1 stop
BQN
ORD
8h 15m
1 stop
Depart: Fri Aug 18 2017 Return: Mon Aug 21 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 56m
1 stop
SJU
ORD
6h 52m
1 stop
Depart: Thu Sep 28 2017 Return: Tue Oct 3 2017 Trip spans 6 days
United
United
ORD
SJU
4h 45m
nonstop
SJU
ORD
5h 10m
nonstop
Depart: Wed Sep 6 2017 Return: Thu Sep 21 2017 Trip spans 16 days
Delta
Delta
MDW
SJU
6h 32m
1 stop
SJU
MDW
8h 17m
1 stop
Depart: Mon Jun 26 2017 Return: Mon Jul 3 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
SJU
7h 59m
1 stop
SJU
ORD
5h 13m
nonstop
Depart: Mon Oct 23 2017 Return: Sun Oct 29 2017 Trip spans 7 days
Major Airline
Major Airline
ORD
BQN
18h 04m
1 stop
BQN
ORD
30h 07m
1 stop
Depart: Thu Oct 12 2017 Return: Mon Oct 16 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 53m
1 stop
SJU
ORD
6h 44m
1 stop
Depart: Wed Nov 1 2017 Return: Sat Nov 4 2017 Trip spans 4 days
Major Airline
Major Airline
ORD
BQN
15h 56m
1 stop
BQN
ORD
6h 25m
1 stop
Depart: Fri Oct 20 2017 Return: Tue Oct 24 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 53m
1 stop
SJU
ORD
8h 32m
1 stop
Depart: Wed Oct 4 2017 Return: Tue Oct 10 2017 Trip spans 7 days
Delta
Delta
MDW
SJU
6h 32m
1 stop
SJU
MDW
9h 48m
1 stop
Depart: Wed Aug 16 2017 Return: Mon Aug 21 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
SJU
8h 30m
nonstop
SJU
ORD
6h 43m
nonstop
Depart: Wed Oct 18 2017 Return: Wed Oct 25 2017 Trip spans 8 days
Delta
Delta
MDW
SJU
8h 34m
1 stop
SJU
MDW
7h 12m
1 stop
Depart: Fri Jun 23 2017 Return: Mon Jul 3 2017 Trip spans 11 days
Spirit Airlines
Spirit Airlines
ORD
BQN
8h 14m
1 stop
BQN
ORD
8h 54m
1 stop
Depart: Fri Jul 21 2017 Return: Sat Jul 29 2017 Trip spans 9 days
United
United
ORD
SJU
4h 45m
nonstop
SJU
ORD
5h 10m
nonstop
Depart: Tue Sep 5 2017 Return: Sat Sep 9 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
SJU
7h 17m
nonstop
SJU
ORD
9h 43m
nonstop
Depart: Tue Sep 26 2017 Return: Tue Oct 3 2017 Trip spans 8 days
Delta
Delta
MDW
SJU
8h 34m
1 stop
SJU
MDW
8h 12m
1 stop
Depart: Wed Sep 27 2017 Return: Sun Oct 1 2017 Trip spans 5 days
JetBlue
JetBlue
ORD
PSE
13h 35m
2 stops
PSE
ORD
28h 08m
1 stop
Depart: Thu Sep 7 2017 Return: Mon Sep 11 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
SJU
15h 20m
nonstop
SJU
ORD
15h 34m
nonstop
Depart: Tue Jun 13 2017 Return: Tue Jun 20 2017 Trip spans 8 days
United
United
ORD
SJU
8h 30m
1 stop
SJU
ORD
10h 40m
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.

^ The fares displayed in KAYAK ads found on other sites include all taxes and fees for economy class travel and were found by KAYAK users in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.
Airports
Origin

Chicago
only $305
only $382
Destination

Aguadilla
$305
San Juan
$330
Ponce
$481