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: Tue Aug 22 2017 Return: Tue Aug 29 2017 Trip spans 8 days
Frontier
Frontier
SJU
11:05p
ORD
4:42p
17h 37m
1 stop
ORD
2:00a
SJU
7:40p
17h 40m
1 stop
Depart: Fri Aug 11 2017 Return: Sat Aug 26 2017 Trip spans 16 days
Spirit Airlines
Spirit Airlines
BQN
10:59p
ORD
7:53a
8h 54m
1 stop
ORD
12:45p
BQN
8:59p
8h 14m
1 stop
Depart: Fri Aug 4 2017 Return: Tue Aug 22 2017 Trip spans 19 days
JetBlue
JetBlue
SJU
12:59p
ORD
7:42p
6h 43m
nonstop
ORD
3:00a
SJU
12:07p
9h 07m
1 stop
Depart: Fri Oct 6 2017 Return: Sun Oct 8 2017 Trip spans 3 days
United
United
SJU
10:30a
ORD
3:35p
5h 05m
nonstop
ORD
3:50a
SJU
8:30a
4h 40m
nonstop
Depart: Sun Dec 17 2017 Return: Thu Jan 4 2018 Trip spans 19 days
Delta
Delta
SJU
3:00a
ORD
10:51a
7h 51m
1 stop
ORD
1:00a
SJU
7:22a
6h 22m
1 stop
Depart: Mon Aug 28 2017 Return: Tue Sep 5 2017 Trip spans 9 days
Frontier
Frontier
SJU
11:05p
ORD
4:42p
17h 37m
1 stop
ORD
2:00a
SJU
7:40p
17h 40m
1 stop
Depart: Mon Sep 11 2017 Return: Tue Sep 26 2017 Trip spans 16 days
Frontier
Frontier
SJU
10:25p
ORD
4:25p
18h 00m
1 stop
ORD
2:00a
SJU
7:39p
17h 39m
1 stop
Depart: Sun Dec 31 2017 Return: Sun Jan 7 2018 Trip spans 8 days
American Airlines
American Airlines
SJU
2:40a
ORD
9:54a
7h 14m
1 stop
ORD
12:27a
SJU
9:13a
8h 46m
1 stop
Depart: Fri Sep 8 2017 Return: Sun Sep 24 2017 Trip spans 17 days
Spirit Airlines
Spirit Airlines
SJU
10:12a
ORD
4:55p
6h 43m
1 stop
ORD
1:15a
SJU
8:11a
6h 56m
1 stop
Depart: Sat Sep 9 2017 Return: Wed Sep 13 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJU
12:23p
ORD
8:55p
8h 32m
1 stop
ORD
1:15a
SJU
8:11a
6h 56m
1 stop
Depart: Wed Aug 9 2017 Return: Sat Aug 12 2017 Trip spans 4 days
Frontier
Frontier
SJU
11:05p
ORD
4:32p
17h 27m
1 stop
ORD
2:25a
SJU
7:40p
17h 15m
1 stop
Depart: Sat Dec 23 2017 Return: Sat Jan 6 2018 Trip spans 15 days
United
United
SJU
9:55p
ORD
3:05a
5h 10m
nonstop
ORD
2:15p
SJU
6:50p
4h 35m
nonstop
Depart: Wed Nov 22 2017 Return: Tue Nov 28 2017 Trip spans 7 days
JetBlue
JetBlue
SJU
9:25a
ORD
8:07p
10h 42m
1 stop
ORD
2:00a
SJU
11:56a
9h 56m
1 stop
Depart: Wed Sep 13 2017 Return: Sun Sep 17 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJU
12:23p
ORD
8:58p
8h 35m
1 stop
ORD
1:15a
SJU
8:11a
6h 56m
1 stop
Depart: Thu Aug 10 2017 Return: Sat Aug 12 2017 Trip spans 3 days
Frontier
Frontier
SJU
11:05p
ORD
4:32p
17h 27m
1 stop
ORD
2:25a
SJU
7:40p
17h 15m
1 stop
Depart: Sun Dec 24 2017 Return: Sat Jan 6 2018 Trip spans 14 days
United
United
SJU
1:00a
ORD
6:10a
5h 10m
nonstop
ORD
2:15p
SJU
6:50p
4h 35m
nonstop
Depart: Thu Sep 14 2017 Return: Sun Sep 17 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
SJU
12:23p
ORD
8:58p
8h 35m
1 stop
ORD
1:15a
SJU
8:11a
6h 56m
1 stop
Depart: Tue Nov 21 2017 Return: Tue Nov 28 2017 Trip spans 8 days
JetBlue
JetBlue
SJU
9:25a
ORD
8:07p
10h 42m
1 stop
ORD
2:00a
SJU
11:56a
9h 56m
1 stop
Depart: Wed Aug 16 2017 Return: Tue Aug 22 2017 Trip spans 7 days
Frontier
Frontier
SJU
11:05p
ORD
4:42p
17h 37m
1 stop
ORD
2:00a
SJU
7:40p
17h 40m
1 stop
Depart: Tue Dec 19 2017 Return: Sun Jan 14 2018 Trip spans 27 days
United
United
SJU
10:10a
ORD
3:20p
5h 10m
nonstop
ORD
8:00a
SJU
5:50p
9h 50m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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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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.

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Airports
Origin

Aguadilla
$301
San Juan
$279
Destination

Chicago
$279
Airlines Airline reviews

55 travelers who booked a flight from San Juan to Chicago rated their chosen airlines with an average of 7.9.

Overall
8.4
Boarding
8.3
Crew
8.4
Comfort
8.1
Food
7.3
Entertainment
7.3