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
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 May 9 2017 Return: Tue May 16 2017 Trip spans 8 days
JetBlue
JetBlue
SJU
10:31a
ORD
7:18p
8h 47m
1 stop
ORD
2:19a
SJU
10:49a
8h 30m
1 stop
Depart: Thu Apr 27 2017 Return: Tue May 2 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
12:17p
ORD
8:59p
8h 42m
1 stop
ORD
1:17p
SJU
8:05a
18h 48m
1 stop
Depart: Wed Mar 29 2017 Return: Mon Apr 3 2017 Trip spans 6 days
United
United
SJU
9:02p
ORD
7:01a
9h 59m
1 stop
ORD
5:15p
SJU
7:15a
14h 00m
2 stops
Depart: Tue May 2 2017 Return: Mon May 8 2017 Trip spans 7 days
Major Airline
Major Airline
SJU
12:59p
ORD
3:18p
26h 19m
nonstop
ORD
10:19p
SJU
11:30p
25h 11m
nonstop
Depart: Sun Apr 2 2017 Return: Sun Apr 23 2017 Trip spans 22 days
American Airlines
American Airlines
SJU
11:55a
ORD
5:22p
5h 27m
nonstop
ORD
5:40a
SJU
10:14a
4h 34m
nonstop
Depart: Wed Apr 12 2017 Return: Sun Apr 16 2017 Trip spans 5 days
Delta
Delta
SJU
11:45a
ORD
8:39p
8h 54m
1 stop
ORD
2:00a
SJU
8:20a
6h 20m
1 stop
Depart: Fri Apr 28 2017 Return: Tue May 2 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJU
12:17p
ORD
8:59p
8h 42m
1 stop
ORD
1:17p
SJU
8:05a
18h 48m
1 stop
Depart: Wed May 3 2017 Return: Mon May 8 2017 Trip spans 6 days
JetBlue
JetBlue
SJU
10:31a
ORD
7:18p
8h 47m
1 stop
ORD
2:19a
SJU
10:49a
8h 30m
1 stop
Depart: Wed May 17 2017 Return: Mon May 22 2017 Trip spans 6 days
Major Airline
Major Airline
SJU
2:57a
ORD
12:38a
21h 41m
nonstop
ORD
10:19p
SJU
6:49a
8h 30m
nonstop
Depart: Fri Mar 3 2017 Return: Mon Mar 6 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
SJU
12:28p
ORD
8:29a
20h 01m
1 stop
ORD
1:19p
SJU
7:07a
17h 48m
1 stop
Depart: Tue Mar 14 2017 Return: Tue Mar 21 2017 Trip spans 8 days
JetBlue
JetBlue
SJU
10:21a
ORD
8:09p
9h 48m
1 stop
ORD
3:00a
SJU
11:27a
8h 27m
1 stop
Depart: Wed Apr 5 2017 Return: Tue Apr 11 2017 Trip spans 7 days
United
United
SJU
10:22a
ORD
3:32p
5h 10m
nonstop
ORD
3:42a
SJU
8:27a
4h 45m
nonstop
Depart: Thu Jul 27 2017 Return: Mon Sep 4 2017 Trip spans 40 days
American Airlines
American Airlines
SJU
10:55a
ORD
3:57p
5h 02m
nonstop
ORD
5:05a
SJU
10:00a
4h 55m
nonstop
Depart: Sat Apr 29 2017 Return: Mon May 1 2017 Trip spans 3 days
Delta
Delta
SJU
3:00a
ORD
12:51p
9h 51m
1 stop
ORD
2:00a
SJU
9:52a
7h 52m
1 stop
Depart: Thu Feb 23 2017 Return: Tue Feb 28 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
12:28p
ORD
8:29a
20h 01m
1 stop
ORD
1:14p
SJU
7:07a
17h 53m
1 stop
Depart: Tue Apr 25 2017 Return: Wed May 3 2017 Trip spans 9 days
JetBlue
JetBlue
SJU
10:21a
ORD
8:10p
9h 49m
1 stop
ORD
2:19a
SJU
10:49a
8h 30m
1 stop
Depart: Thu May 18 2017 Return: Fri May 19 2017 Trip spans 2 days
United
United
SJU
10:10a
ORD
3:20p
5h 10m
nonstop
ORD
3:30a
SJU
8:15a
4h 45m
nonstop
Depart: Wed Aug 2 2017 Return: Wed Aug 9 2017 Trip spans 8 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 May 24 2017 Return: Tue May 30 2017 Trip spans 7 days
Delta
Delta
SJU
3:25a
ORD
11:01a
7h 36m
1 stop
ORD
2:00a
SJU
9:52a
7h 52m
1 stop
Depart: Thu Mar 9 2017 Return: Mon Mar 13 2017 Trip spans 4 days
Major Airline
Major Airline
SJU
5:21a
ORD
3:09p
9h 48m
nonstop
ORD
11:00p
SJU
3:27a
28h 27m
nonstop
* 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
$295
Destination

Chicago
$295
Airlines Airline reviews

37 travelers who booked a flight from San Juan to Chicago rated their chosen airlines with an average of 8.1.

Overall
8.5
Boarding
8.3
Crew
8.4
Comfort
8.4
Food
7.4
Entertainment
7.8