Find Cheap Flights to Puerto Rico

Depart
Return
1 adult
Cabin Economy
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
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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: Tue Nov 7 2017 Return: Tue Dec 5 2017 Trip spans 29 days
$260
Select
Multiple Airlines
Multiple Airlines
MDW
→
SJU
7h 34m
1 stop
SJU
→
MDW
8h 23m
1 stop
Depart: Mon Sep 25 2017 Return: Tue Oct 3 2017 Trip spans 9 days
$262
Select
Spirit Airlines
Spirit Airlines
ORD
→
SJU
9h 10m
1 stop
SJU
→
ORD
6h 45m
1 stop
Depart: Sat Aug 26 2017 Return: Mon Aug 28 2017 Trip spans 3 days
$279
Select
Frontier
Frontier
ORD
→
SJU
17h 40m
1 stop
SJU
→
ORD
17h 37m
1 stop
Depart: Wed Sep 27 2017 Return: Tue Oct 3 2017 Trip spans 7 days
$357
Select
Delta
Delta
MDW
→
SJU
13h 37m
2 stops
SJU
→
MDW
10h 32m
2 stops
Depart: Mon Jan 15 2018 Return: Tue Jan 23 2018 Trip spans 9 days
$385
Select
JetBlue
JetBlue
ORD
→
SJU
6h 49m
nonstop
SJU
→
ORD
6h 50m
nonstop
Depart: Sat Jan 20 2018 Return: Sun Jan 21 2018 Trip spans 2 days
$438
Select
United
United
ORD
→
SJU
4h 35m
nonstop
SJU
→
ORD
10h 51m
1 stop
Depart: Tue Nov 7 2017 Return: Tue Dec 5 2017 Trip spans 29 days
$260
Select
Multiple Airlines
Multiple Airlines
ORD
→
SJU
7h 34m
1 stop
SJU
→
ORD
9h 08m
1 stop
Depart: Sat Nov 4 2017 Return: Mon Nov 6 2017 Trip spans 3 days
$266
Select
Spirit Airlines
Spirit Airlines
ORD
→
BQN
7h 33m
1 stop
BQN
→
ORD
7h 23m
1 stop
Depart: Fri Jul 21 2017 Return: Sun Jul 30 2017 Trip spans 10 days
$553
Select
American Airlines
American Airlines
ORD
→
SJU
4h 44m
nonstop
SJU
→
ORD
5h 15m
nonstop
Depart: Tue Sep 12 2017 Return: Tue Sep 19 2017 Trip spans 8 days
$279
Select
Frontier
Frontier
ORD
→
SJU
17h 39m
1 stop
SJU
→
ORD
18h 00m
1 stop
Depart: Mon Oct 16 2017 Return: Sat Oct 21 2017 Trip spans 6 days
$270
Select
Spirit Airlines
Spirit Airlines
ORD
→
SJU
8h 25m
1 stop
SJU
→
ORD
8h 35m
1 stop
Depart: Sun Aug 20 2017 Return: Tue Aug 22 2017 Trip spans 3 days
$300
Select
Frontier
Frontier
ORD
→
SJU
17h 40m
1 stop
SJU
→
ORD
17h 37m
1 stop
Depart: Wed Sep 13 2017 Return: Tue Sep 19 2017 Trip spans 7 days
$274
Select
Spirit Airlines
Spirit Airlines
ORD
→
SJU
6h 56m
1 stop
SJU
→
ORD
8h 35m
1 stop
Depart: Wed Aug 23 2017 Return: Sun Aug 27 2017 Trip spans 5 days
$305
Select
Multiple Airlines
Multiple Airlines
ORD
→
SJU
9h 07m
1 stop
SJU
→
ORD
17h 37m
1 stop
Depart: Wed Oct 11 2017 Return: Wed Oct 18 2017 Trip spans 8 days
$357
Select
Delta
Delta
MDW
→
SJU
13h 53m
2 stops
SJU
→
MDW
10h 37m
2 stops
Depart: Mon Aug 21 2017 Return: Tue Aug 22 2017 Trip spans 2 days
$300
Select
Frontier
Frontier
ORD
→
SJU
17h 40m
1 stop
SJU
→
ORD
17h 37m
1 stop
Depart: Wed Oct 18 2017 Return: Mon Oct 23 2017 Trip spans 6 days
$274
Select
Spirit Airlines
Spirit Airlines
ORD
→
SJU
6h 56m
1 stop
SJU
→
ORD
8h 35m
1 stop
Depart: Thu Oct 5 2017 Return: Tue Oct 10 2017 Trip spans 6 days
$310
Select
Multiple Airlines
Multiple Airlines
MDW
→
SJU
7h 53m
1 stop
SJU
→
MDW
8h 32m
1 stop
Depart: Thu Oct 19 2017 Return: Tue Oct 24 2017 Trip spans 6 days
$274
Select
Spirit Airlines
Spirit Airlines
ORD
→
SJU
6h 56m
1 stop
SJU
→
ORD
8h 35m
1 stop
Depart: Mon Sep 25 2017 Return: Wed Sep 27 2017 Trip spans 3 days
$373
Select
Delta
Delta
MDW
→
SJU
6h 23m
1 stop
SJU
→
MDW
10h 50m
2 stops
* 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 $260
only $260
Destination
Aguadilla
$266
San Juan
$260