Find Deals on Flights from Puerto Rico to Chicago O'Hare International

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.
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Book cheap flights from Puerto Rico to Chicago O'Hare International

(Round-trip)
Depart: Tue Jan 10 2017 Return: Tue Jan 17 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
SJU
10:08a
ORD
5:33a
19h 25m
1 stop
ORD
2:58p
SJU
4:37a
13h 39m
1 stop
Depart: Thu Mar 2 2017 Return: Sun Mar 5 2017 Trip spans 4 days
JetBlue
JetBlue
SJU
10:21a
ORD
8:10p
9h 49m
1 stop
ORD
2:00a
SJU
10:28a
8h 28m
1 stop
Depart: Mon Mar 13 2017 Return: Mon Mar 20 2017 Trip spans 8 days
Major Airline
Major Airline
SJU
6:17p
ORD
4:10p
21h 53m
nonstop
ORD
11:00p
SJU
11:10a
12h 10m
nonstop
Depart: Thu Feb 9 2017 Return: Sun Feb 12 2017 Trip spans 4 days
United
United
SJU
9:05p
ORD
10:38a
13h 33m
2 stops
ORD
4:10p
SJU
6:15a
14h 05m
2 stops
Depart: Fri Feb 17 2017 Return: Mon Feb 20 2017 Trip spans 4 days
American Airlines
American Airlines
SJU
10:57a
ORD
4:24p
5h 27m
nonstop
ORD
3:40a
SJU
8:10a
4h 30m
nonstop
Depart: Thu Dec 15 2016 Return: Wed Jan 4 2017 Trip spans 21 days
Delta
Delta
SJU
12:00p
ORD
8:34p
8h 34m
1 stop
ORD
10:35a
SJU
5:05p
6h 30m
1 stop
Depart: Fri Feb 3 2017 Return: Tue Feb 7 2017 Trip spans 5 days
JetBlue
JetBlue
SJU
10:28a
ORD
8:17p
9h 49m
1 stop
ORD
2:12a
SJU
12:31p
10h 19m
1 stop
Depart: Wed Jan 18 2017 Return: Wed Jan 25 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
SJU
3:44p
ORD
5:33a
13h 49m
1 stop
ORD
12:15a
SJU
12:44p
12h 29m
1 stop
Depart: Mon Jan 16 2017 Return: Mon Feb 20 2017 Trip spans 36 days
Major Airline
Major Airline
SJU
8:11p
ORD
4:44a
8h 33m
1 stop
ORD
9:00p
SJU
5:33a
8h 33m
1 stop
Depart: Fri Jan 27 2017 Return: Mon Jan 30 2017 Trip spans 4 days
Major Airline
Major Airline
SJU
12:34a
ORD
3:16p
14h 42m
nonstop
ORD
9:12p
SJU
7:29a
10h 17m
nonstop
Depart: Fri Mar 3 2017 Return: Sun Mar 5 2017 Trip spans 3 days
JetBlue
JetBlue
SJU
10:21a
ORD
8:10p
9h 49m
1 stop
ORD
2:00a
SJU
10:28a
8h 28m
1 stop
Depart: Tue Jan 24 2017 Return: Thu Feb 2 2017 Trip spans 10 days
Spirit Airlines
Spirit Airlines
SJU
3:44p
ORD
5:33a
13h 49m
1 stop
ORD
1:15p
SJU
7:08a
17h 53m
1 stop
Depart: Wed Jan 25 2017 Return: Sun Jan 29 2017 Trip spans 5 days
United
United
SJU
9:05p
ORD
7:04a
9h 59m
1 stop
ORD
2:40a
SJU
7:05a
4h 25m
nonstop
Depart: Thu Apr 27 2017 Return: Sun Apr 30 2017 Trip spans 4 days
American Airlines
American Airlines
SJU
10:55a
ORD
3:57p
5h 02m
nonstop
ORD
5:05a
SJU
10:00a
4h 55m
nonstop
Depart: Tue Mar 14 2017 Return: Tue Mar 21 2017 Trip spans 8 days
JetBlue
JetBlue
SJU
10:21a
ORD
8:10p
9h 49m
1 stop
ORD
3:00a
SJU
11:28a
8h 28m
1 stop
Depart: Thu Jan 12 2017 Return: Mon Jan 16 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJU
7:50a
ORD
7:57p
12h 07m
1 stop
ORD
2:58p
SJU
4:37a
13h 39m
1 stop
Depart: Thu Feb 16 2017 Return: Mon Feb 20 2017 Trip spans 5 days
United
United
SJU
10:10a
ORD
3:10p
5h 00m
nonstop
ORD
2:35a
SJU
7:00a
4h 25m
nonstop
Depart: Fri May 12 2017 Return: Mon May 15 2017 Trip spans 4 days
American Airlines
American Airlines
SJU
10:55a
ORD
3:57p
5h 02m
nonstop
ORD
5:05a
SJU
10:00a
4h 55m
nonstop
Depart: Wed Mar 15 2017 Return: Tue Mar 21 2017 Trip spans 7 days
JetBlue
JetBlue
SJU
10:21a
ORD
8:10p
9h 49m
1 stop
ORD
3:00a
SJU
11:28a
8h 28m
1 stop
Depart: Fri Jan 13 2017 Return: Mon Jan 16 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
SJU
12:41p
ORD
8:12a
19h 31m
1 stop
ORD
2:58p
SJU
4:37a
13h 39m
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.

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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

San Juan
$243
Destination

Chicago
$243
Airlines Airline reviews

29 travelers who booked a flight from San Juan to Chicago rated their chosen airlines with an average of 8.2.

Overall
8.6
Boarding
8.4
Crew
8.4
Comfort
8.5
Food
7.8
Entertainment
7.7