Find Cheap Flights from Chicago O'Hare International to San Juan

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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

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

Book cheap flights from Chicago O'Hare International to San Juan

(Round-trip)
Depart: Wed Oct 11 2017 Return: Tue Oct 17 2017 Trip spans 7 days
Frontier
Frontier
ORD
2:00a
SJU
9:11p
19h 11m
1 stop
SJU
11:15p
ORD
10:29a
11h 14m
1 stop
Depart: Fri Sep 22 2017 Return: Sat Sep 30 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
ORD
1:23p
SJU
8:11a
18h 48m
1 stop
SJU
12:23p
ORD
8:58p
8h 35m
1 stop
Depart: Tue Oct 31 2017 Return: Tue Nov 7 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
4:25a
SJU
9:07a
4h 42m
nonstop
SJU
5:45a
ORD
3:29p
9h 44m
1 stop
Depart: Fri Jan 5 2018 Return: Fri Mar 2 2018 Trip spans 57 days
United
United
ORD
5:20p
SJU
9:55p
4h 35m
nonstop
SJU
10:45p
ORD
8:03a
9h 18m
1 stop
Depart: Tue Nov 28 2017 Return: Mon Dec 4 2017 Trip spans 7 days
Frontier
Frontier
ORD
1:00a
SJU
8:07p
19h 07m
1 stop
SJU
10:55p
ORD
10:38a
11h 43m
1 stop
Depart: Wed Nov 29 2017 Return: Mon Dec 4 2017 Trip spans 6 days
Frontier
Frontier
ORD
1:00a
SJU
8:07p
19h 07m
1 stop
SJU
10:55p
ORD
10:38a
11h 43m
1 stop
Depart: Wed Dec 6 2017 Return: Mon Dec 11 2017 Trip spans 6 days
Frontier
Frontier
ORD
1:00a
SJU
8:07p
19h 07m
1 stop
SJU
11:10p
ORD
10:46a
11h 36m
1 stop
Depart: Mon Nov 6 2017 Return: Fri Nov 10 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
12:23p
SJU
7:09a
18h 46m
1 stop
SJU
12:28p
ORD
8:00a
19h 32m
1 stop
Depart: Tue Dec 12 2017 Return: Tue Dec 19 2017 Trip spans 8 days
Frontier
Frontier
ORD
1:00a
SJU
8:09p
19h 09m
1 stop
SJU
11:10p
ORD
10:46a
11h 36m
1 stop
Depart: Wed Dec 13 2017 Return: Tue Dec 19 2017 Trip spans 7 days
Frontier
Frontier
ORD
1:00a
SJU
8:09p
19h 09m
1 stop
SJU
11:10p
ORD
10:46a
11h 36m
1 stop
Depart: Mon Sep 11 2017 Return: Sat Sep 16 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
1:23p
SJU
8:11a
18h 48m
1 stop
SJU
12:23p
ORD
8:58p
8h 35m
1 stop
Depart: Tue Jan 23 2018 Return: Mon Feb 5 2018 Trip spans 14 days
Frontier
Frontier
ORD
1:00a
SJU
8:09p
19h 09m
1 stop
SJU
11:10p
ORD
10:46a
11h 36m
1 stop
Depart: Sat Oct 14 2017 Return: Mon Oct 16 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
ORD
1:23p
SJU
8:11a
18h 48m
1 stop
SJU
12:23p
ORD
6:49a
18h 26m
1 stop
Depart: Thu Jan 4 2018 Return: Wed Jan 10 2018 Trip spans 7 days
United
United
ORD
1:00a
SJU
5:50p
16h 50m
1 stop
SJU
8:58p
ORD
8:19a
11h 21m
1 stop
Depart: Wed Jan 24 2018 Return: Mon Feb 5 2018 Trip spans 13 days
Frontier
Frontier
ORD
1:00a
SJU
8:09p
19h 09m
1 stop
SJU
11:10p
ORD
10:46a
11h 36m
1 stop
Depart: Sat Sep 9 2017 Return: Mon Sep 11 2017 Trip spans 3 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 Nov 22 2017 Return: Thu Nov 30 2017 Trip spans 9 days
United
United
ORD
4:23p
SJU
9:27a
17h 04m
1 stop
SJU
10:10a
ORD
3:20p
5h 10m
nonstop
Depart: Tue Jan 30 2018 Return: Mon Feb 5 2018 Trip spans 7 days
Frontier
Frontier
ORD
1:00a
SJU
8:09p
19h 09m
1 stop
SJU
11:10p
ORD
10:46a
11h 36m
1 stop
Depart: Tue Oct 3 2017 Return: Mon Oct 9 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
1:23p
SJU
8:11a
18h 48m
1 stop
SJU
12:23p
ORD
6:49a
18h 26m
1 stop
Depart: Wed Jan 31 2018 Return: Tue Feb 27 2018 Trip spans 28 days
Frontier
Frontier
ORD
1:00a
SJU
8:09p
19h 09m
1 stop
SJU
11:10p
ORD
10:46a
11h 36m
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
$235
Destination

San Juan
$235
Airlines Airline reviews

39 travelers who booked a flight from Chicago to San Juan rated their chosen airlines with an average of 7.0.

Overall
7.4
Boarding
6.8
Crew
7.4
Comfort
6.8
Food
6.6
Entertainment
7.1