Find Deals on 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 Apr 3 2017 Return: Tue Apr 25 2017 Trip spans 23 days
Major Airline
Major Airline
ORD
SJU
8h 27m
nonstop
SJU
ORD
6h 56m
nonstop
Depart: Tue Apr 4 2017 Return: Tue Apr 25 2017 Trip spans 22 days
JetBlue
JetBlue
ORD
SJU
8h 27m
1 stop
SJU
ORD
9h 49m
1 stop
Depart: Mon Mar 13 2017 Return: Mon Mar 20 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
BQN
6h 57m
1 stop
BQN
ORD
9h 22m
1 stop
Depart: Sat Apr 1 2017 Return: Tue Apr 4 2017 Trip spans 4 days
United
United
ORD
SJU
12h 44m
2 stops
SJU
ORD
9h 00m
1 stop
Depart: Fri Aug 18 2017 Return: Fri Aug 25 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
SJU
4h 55m
nonstop
SJU
ORD
5h 02m
nonstop
Depart: Mon Mar 20 2017 Return: Wed Mar 22 2017 Trip spans 3 days
Delta
Delta
MDW
SJU
6h 51m
1 stop
SJU
MDW
7h 02m
1 stop
Depart: Tue Apr 18 2017 Return: Tue Apr 25 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SJU
24h 20m
nonstop
SJU
ORD
9h 49m
nonstop
Depart: Thu Apr 27 2017 Return: Mon May 1 2017 Trip spans 5 days
JetBlue
JetBlue
ORD
BQN
18h 10m
1 stop
BQN
ORD
20h 47m
1 stop
Depart: Sun May 28 2017 Return: Sat Jun 3 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
BQN
7h 58m
1 stop
BQN
ORD
8h 28m
1 stop
Depart: Fri May 19 2017 Return: Sat May 27 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
BQN
9h 06m
1 stop
BQN
ORD
12h 48m
1 stop
Depart: Fri Jun 2 2017 Return: Sun Jun 25 2017 Trip spans 24 days
Spirit Airlines
Spirit Airlines
ORD
BQN
7h 58m
1 stop
BQN
ORD
8h 27m
1 stop
Depart: Mon Apr 3 2017 Return: Wed Apr 5 2017 Trip spans 3 days
Delta
Delta
MDW
SJU
6h 30m
1 stop
SJU
MDW
9h 02m
1 stop
Depart: Fri Jun 23 2017 Return: Sun Jun 25 2017 Trip spans 3 days
Major Airline
Major Airline
ORD
BQN
11h 40m
1 stop
BQN
ORD
30h 31m
1 stop
Depart: Sat Aug 26 2017 Return: Sat Sep 2 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
SJU
4h 55m
nonstop
SJU
ORD
5h 02m
nonstop
Depart: Sat Apr 15 2017 Return: Fri Apr 21 2017 Trip spans 7 days
United
United
ORD
SJU
4h 45m
nonstop
SJU
ORD
7h 45m
1 stop
Depart: Tue Apr 11 2017 Return: Tue Apr 18 2017 Trip spans 8 days
Delta
Delta
MDW
SJU
6h 21m
1 stop
SJU
MDW
7h 18m
1 stop
Depart: Tue Mar 21 2017 Return: Thu Mar 30 2017 Trip spans 10 days
Major Airline
Major Airline
ORD
SJU
17h 10m
2 stops
SJU
ORD
15h 11m
2 stops
Depart: Sat Apr 29 2017 Return: Sat May 6 2017 Trip spans 8 days
Delta
Delta
MDW
SJU
7h 50m
1 stop
SJU
MDW
8h 22m
1 stop
Depart: Sat Apr 22 2017 Return: Sat Apr 29 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SJU
17h 49m
1 stop
SJU
ORD
8h 42m
1 stop
Depart: Wed Mar 22 2017 Return: Mon Mar 27 2017 Trip spans 6 days
JetBlue
JetBlue
ORD
SJU
7h 19m
1 stop
SJU
ORD
27h 11m
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
only $294
only $362
Destination

Aguadilla
$312
San Juan
$294