Find Cheap Flights from Puerto Rico to Chicago

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

(Round-trip)
Depart: Mon Sep 11 2017 Return: Tue Sep 19 2017 Trip spans 9 days
Frontier
Frontier
SJU
ORD
18h 30m
1 stop
ORD
SJU
16h 49m
1 stop
Depart: Wed Dec 6 2017 Return: Thu Dec 7 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
SJU
ORD
7h 30m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Tue Aug 22 2017 Return: Tue Aug 29 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
SJU
ORD
6h 52m
1 stop
ORD
SJU
9h 07m
1 stop
Depart: Tue Oct 3 2017 Return: Tue Oct 10 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
17h 02m
2 stops
MDW
SJU
13h 53m
2 stops
Depart: Tue Jul 11 2017 Return: Wed Jul 26 2017 Trip spans 16 days
United
United
SJU
ORD
13h 40m
1 stop
ORD
SJU
14h 23m
1 stop
Depart: Mon Aug 7 2017 Return: Thu Aug 10 2017 Trip spans 4 days
Major Airline
Major Airline
SJU
ORD
27h 26m
nonstop
ORD
SJU
11h 18m
nonstop
Depart: Mon Sep 11 2017 Return: Tue Sep 26 2017 Trip spans 16 days
Frontier
Frontier
SJU
ORD
18h 30m
1 stop
ORD
SJU
16h 49m
1 stop
Depart: Tue Sep 12 2017 Return: Tue Sep 19 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
SJU
ORD
6h 44m
1 stop
ORD
SJU
12h 32m
1 stop
Depart: Thu Aug 17 2017 Return: Mon Aug 21 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJU
ORD
6h 52m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Tue Aug 15 2017 Return: Sun Aug 20 2017 Trip spans 6 days
Frontier
Frontier
SJU
ORD
18h 02m
1 stop
ORD
SJU
17h 26m
1 stop
Depart: Thu Oct 19 2017 Return: Sun Oct 29 2017 Trip spans 11 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 32m
1 stop
ORD
SJU
6h 53m
1 stop
Depart: Tue Sep 12 2017 Return: Mon Sep 18 2017 Trip spans 7 days
Frontier
Frontier
SJU
ORD
18h 30m
1 stop
ORD
SJU
16h 49m
1 stop
Depart: Tue Sep 19 2017 Return: Wed Sep 27 2017 Trip spans 9 days
Delta
Delta
SJU
MDW
9h 48m
1 stop
MDW
SJU
13h 53m
2 stops
Depart: Thu Jul 27 2017 Return: Tue Aug 8 2017 Trip spans 13 days
Multiple Airlines
Multiple Airlines
SJU
ORD
15h 26m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Sun Nov 5 2017 Return: Sat Nov 11 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
SJU
ORD
6h 44m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Wed Oct 4 2017 Return: Wed Oct 11 2017 Trip spans 8 days
Frontier
Frontier
SJU
ORD
18h 30m
1 stop
ORD
SJU
16h 49m
1 stop
Depart: Fri Jul 28 2017 Return: Sat Aug 12 2017 Trip spans 16 days
United
United
SJU
ORD
18h 27m
1 stop
ORD
SJU
4h 45m
nonstop
Depart: Thu Nov 9 2017 Return: Wed Nov 15 2017 Trip spans 7 days
Delta
Delta
SJU
MDW
9h 46m
1 stop
MDW
SJU
15h 24m
2 stops
Depart: Wed Jul 12 2017 Return: Mon Jul 17 2017 Trip spans 6 days
Multiple Airlines
Multiple Airlines
BQN
ORD
30h 06m
1 stop
ORD
BQN
8h 14m
1 stop
Depart: Wed Dec 6 2017 Return: Mon Dec 11 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
7h 30m
1 stop
ORD
SJU
6h 56m
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,
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Airports
Origin

Aguadilla
$366
San Juan
$289
Destination

Chicago
only $289
only $379
Airlines Airline reviews

38 travelers who booked a flight from San Juan to Chicago rated their chosen airlines with an average of 7.7.

Overall
8.1
Boarding
7.9
Crew
8.2
Comfort
7.9
Food
7.0
Entertainment
7.1