Find Cheap 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: Thu Nov 30 2017 Return: Tue Dec 5 2017 Trip spans 6 days
Frontier
Frontier
SJU
12:00a
ORD
3:00p
15h 00m
1 stop
ORD
12:00a
SJU
2:41p
14h 41m
1 stop
Depart: Sat Sep 23 2017 Return: Sat Oct 7 2017 Trip spans 15 days
American Airlines
American Airlines
SJU
12:00a
ORD
7:23a
7h 23m
1 stop
ORD
12:00a
SJU
4:42a
4h 42m
nonstop
Depart: Fri Dec 1 2017 Return: Tue Dec 5 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
SJU
12:00a
ORD
1:31p
13h 31m
1 stop
ORD
12:00a
SJU
6:56a
6h 56m
1 stop
Depart: Thu Feb 1 2018 Return: Mon Feb 5 2018 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJU
12:00a
ORD
8:13a
8h 13m
1 stop
ORD
12:00a
SJU
6:56a
6h 56m
1 stop
Depart: Fri Sep 29 2017 Return: Mon Oct 9 2017 Trip spans 11 days
JetBlue
JetBlue
SJU
12:00a
ORD
6:49a
6h 49m
1 stop
ORD
12:00a
SJU
6:41a
6h 41m
1 stop
Depart: Sun Oct 8 2017 Return: Sun Oct 15 2017 Trip spans 8 days
United
United
SJU
12:00a
ORD
5:05a
5h 05m
nonstop
ORD
12:00a
SJU
4:40a
4h 40m
nonstop
Depart: Fri Nov 17 2017 Return: Mon Nov 27 2017 Trip spans 11 days
Delta
Delta
SJU
12:00a
ORD
8:47a
8h 47m
1 stop
ORD
12:00a
SJU
9:26a
9h 26m
1 stop
Depart: Tue Dec 5 2017 Return: Sun Dec 10 2017 Trip spans 6 days
Frontier
Frontier
SJU
12:00a
ORD
3:00p
15h 00m
1 stop
ORD
12:00a
SJU
2:30p
14h 30m
1 stop
Depart: Sun Oct 29 2017 Return: Mon Nov 6 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
BQN
12:00a
ORD
7:50a
7h 50m
1 stop
ORD
12:00a
BQN
8:03a
8h 03m
1 stop
Depart: Thu Oct 12 2017 Return: Mon Oct 16 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
SJU
12:00a
ORD
8:35a
8h 35m
1 stop
ORD
12:00a
SJU
12:32p
12h 32m
1 stop
Depart: Wed Jan 31 2018 Return: Mon Feb 5 2018 Trip spans 6 days
Frontier
Frontier
SJU
12:00a
ORD
6:25p
18h 25m
1 stop
ORD
12:00a
SJU
2:30p
14h 30m
1 stop
Depart: Sat Dec 23 2017 Return: Sun Dec 31 2017 Trip spans 9 days
United
United
SJU
12:00a
ORD
5:09a
5h 09m
nonstop
ORD
12:00a
SJU
4:35a
4h 35m
nonstop
Depart: Sun Oct 15 2017 Return: Tue Oct 31 2017 Trip spans 17 days
Multiple Airlines
Multiple Airlines
BQN
12:00a
ORD
7:50a
7h 50m
1 stop
ORD
12:00a
BQN
5:48p
17h 48m
2 stops
Depart: Wed Oct 18 2017 Return: Fri Oct 20 2017 Trip spans 3 days
American Airlines
American Airlines
SJU
12:00a
ORD
5:17a
5h 17m
nonstop
ORD
12:00a
SJU
7:18a
7h 18m
1 stop
Depart: Thu Oct 5 2017 Return: Tue Oct 10 2017 Trip spans 6 days
Frontier
Frontier
SJU
12:00a
ORD
6:25p
18h 25m
1 stop
ORD
12:00a
SJU
2:59p
14h 59m
1 stop
Depart: Sat Nov 4 2017 Return: Sat Nov 11 2017 Trip spans 8 days
United
United
BQN
12:00a
ORD
8:31a
8h 31m
1 stop
ORD
12:00a
BQN
1:20p
13h 20m
1 stop
Depart: Sat Oct 14 2017 Return: Sat Oct 28 2017 Trip spans 15 days
Spirit Airlines
Spirit Airlines
BQN
12:00a
ORD
7:50a
7h 50m
1 stop
ORD
12:00a
BQN
7:33a
7h 33m
1 stop
Depart: Sun Sep 24 2017 Return: Sun Oct 1 2017 Trip spans 8 days
American Airlines
American Airlines
SJU
12:00a
ORD
5:17a
5h 17m
nonstop
ORD
12:00a
SJU
4:42a
4h 42m
nonstop
Depart: Sun Nov 5 2017 Return: Sat Nov 11 2017 Trip spans 7 days
United
United
SJU
12:00a
ORD
8:15a
9h 15m
1 stop
ORD
12:00a
SJU
4:35a
4h 35m
nonstop
Depart: Mon Dec 25 2017 Return: Sun Dec 31 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
BQN
12:00a
ORD
8:39a
8h 39m
1 stop
ORD
12:00a
BQN
7:02a
7h 02m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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,
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Airports
Origin

Aguadilla
$341
San Juan
$300
Destination

Chicago
$300
Airlines Airline reviews

58 travelers who booked a flight from San Juan to Chicago rated their chosen airlines with an average of 7.8.

Overall
8.2
Boarding
8.1
Crew
8.2
Comfort
8.0
Food
7.2
Entertainment
7.2