Find Deals on 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
Students
under 26
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 Jan 18 2017 Return: Tue Jan 31 2017 Trip spans 14 days
Spirit Airlines
Spirit Airlines
ORD
12:15a
SJU
7:08a
6h 53m
1 stop
SJU
12:41p
ORD
7:57p
7h 16m
1 stop
Depart: Thu Jan 26 2017 Return: Thu Feb 2 2017 Trip spans 8 days
JetBlue
JetBlue
ORD
2:12a
SJU
6:18p
16h 06m
1 stop
SJU
10:28a
ORD
8:17p
9h 49m
1 stop
Depart: Fri Feb 24 2017 Return: Wed Mar 1 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
9:15a
SJU
5:00p
7h 45m
1 stop
SJU
5:21a
ORD
3:10p
9h 49m
1 stop
Depart: Sun Feb 12 2017 Return: Tue Feb 14 2017 Trip spans 3 days
United
United
ORD
4:10p
SJU
6:15a
14h 05m
2 stops
SJU
9:05p
ORD
5:10p
20h 05m
2 stops
Depart: Fri Apr 28 2017 Return: Fri May 5 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
5:05a
SJU
10:00a
4h 55m
nonstop
SJU
10:55a
ORD
3:57p
5h 02m
nonstop
Depart: Wed Apr 12 2017 Return: Fri Apr 21 2017 Trip spans 10 days
Delta
Delta
ORD
2:00a
SJU
6:39p
16h 39m
1 stop
SJU
3:25a
ORD
9:52a
6h 27m
1 stop
Depart: Tue Jan 31 2017 Return: Wed Feb 8 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
ORD
12:15a
SJU
7:08a
6h 53m
1 stop
SJU
12:41p
ORD
7:58p
7h 17m
1 stop
Depart: Wed Feb 1 2017 Return: Fri Mar 3 2017 Trip spans 31 days
JetBlue
JetBlue
ORD
2:12a
SJU
12:31p
10h 19m
1 stop
SJU
10:21a
ORD
8:10p
9h 49m
1 stop
Depart: Tue Feb 28 2017 Return: Tue Mar 7 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
9:00p
SJU
5:28a
8h 28m
nonstop
SJU
8:04p
ORD
10:52a
14h 48m
nonstop
Depart: Sat Feb 4 2017 Return: Wed Feb 8 2017 Trip spans 5 days
JetBlue
JetBlue
ORD
2:12a
SJU
3:20p
13h 08m
1 stop
SJU
5:34a
ORD
8:17p
14h 43m
1 stop
Depart: Sat Mar 4 2017 Return: Wed Mar 8 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
11:40p
SJU
4:46p
17h 06m
1 stop
SJU
11:59p
ORD
3:10p
15h 11m
1 stop
Depart: Tue Jan 24 2017 Return: Tue Jan 31 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
12:15a
SJU
12:44p
12h 29m
1 stop
SJU
7:50a
ORD
7:57p
12h 07m
1 stop
Depart: Sat Dec 31 2016 Return: Thu Jan 12 2017 Trip spans 13 days
United
United
ORD
2:25p
SJU
7:00p
4h 35m
nonstop
SJU
9:05p
ORD
7:04a
9h 59m
1 stop
Depart: Sat Apr 29 2017 Return: Fri May 5 2017 Trip spans 7 days
American Airlines
American Airlines
ORD
11:30a
SJU
4:25p
4h 55m
nonstop
SJU
10:55a
ORD
3:57p
5h 02m
nonstop
Depart: Wed Mar 1 2017 Return: Mon Mar 6 2017 Trip spans 6 days
JetBlue
JetBlue
ORD
2:00a
SJU
10:28a
8h 28m
1 stop
SJU
4:59a
ORD
8:10p
15h 11m
1 stop
Depart: Wed Jan 25 2017 Return: Tue Jan 31 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
12:15a
SJU
12:44p
12h 29m
1 stop
SJU
7:50a
ORD
7:57p
12h 07m
1 stop
Depart: Sat Jan 21 2017 Return: Mon Jan 30 2017 Trip spans 10 days
Major Airline
Major Airline
ORD
7:59a
SJU
4:45p
8h 46m
1 stop
SJU
8:27a
ORD
3:16p
6h 49m
1 stop
Depart: Sat Jan 7 2017 Return: Thu Jan 19 2017 Trip spans 13 days
United
United
ORD
5:25p
SJU
9:55p
4h 30m
nonstop
SJU
10:10a
ORD
3:10p
5h 00m
nonstop
Depart: Sun Apr 30 2017 Return: Fri May 5 2017 Trip spans 6 days
American Airlines
American Airlines
ORD
5:05a
SJU
10:00a
4h 55m
nonstop
SJU
10:55a
ORD
3:57p
5h 02m
nonstop
Depart: Sun Mar 5 2017 Return: Tue Mar 7 2017 Trip spans 3 days
JetBlue
JetBlue
ORD
2:00a
SJU
10:28a
8h 28m
1 stop
SJU
10:21a
ORD
8:10p
9h 49m
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
$191
Destination

San Juan
$191
Airlines Airline reviews

22 travelers who booked a flight from Chicago to San Juan rated their chosen airlines with an average of 6.4.

Overall
6.7
Boarding
6.1
Crew
6.7
Comfort
6.4
Food
6.2
Entertainment
6.2