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 00m
1 stop
ORD
SJU
17h 39m
1 stop
Depart: Tue Jan 9 2018 Return: Mon Jan 15 2018 Trip spans 7 days
Spirit Airlines
Spirit Airlines
BQN
ORD
8h 39m
1 stop
ORD
BQN
20h 10m
1 stop
Depart: Mon Sep 11 2017 Return: Tue Sep 19 2017 Trip spans 9 days
Multiple Airlines
Multiple Airlines
SJU
ORD
6h 43m
1 stop
ORD
SJU
12h 32m
1 stop
Depart: Tue Sep 19 2017 Return: Sun Sep 24 2017 Trip spans 6 days
United
United
BQN
ORD
13h 57m
1 stop
ORD
BQN
18h 00m
1 stop
Depart: Wed Sep 27 2017 Return: Wed Oct 11 2017 Trip spans 15 days
Delta
Delta
SJU
MDW
9h 36m
1 stop
MDW
SJU
13h 40m
2 stops
Depart: Tue Aug 29 2017 Return: Fri Sep 29 2017 Trip spans 32 days
Major Airline
Major Airline
SJU
MDW
6h 30m
nonstop
MDW
SJU
12h 15m
nonstop
Depart: Mon Oct 2 2017 Return: Tue Oct 10 2017 Trip spans 9 days
Frontier
Frontier
SJU
ORD
18h 00m
1 stop
ORD
SJU
14h 59m
1 stop
Depart: Tue Aug 29 2017 Return: Fri Sep 29 2017 Trip spans 32 days
JetBlue
JetBlue
PSE
ORD
16h 03m
1 stop
ORD
PSE
30h 04m
1 stop
Depart: Mon Sep 11 2017 Return: Tue Sep 19 2017 Trip spans 9 days
Multiple Airlines
Multiple Airlines
SJU
ORD
6h 43m
1 stop
ORD
SJU
12h 32m
1 stop
Depart: Wed Oct 25 2017 Return: Mon Oct 30 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 35m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Mon Sep 25 2017 Return: Tue Oct 10 2017 Trip spans 16 days
Frontier
Frontier
SJU
ORD
18h 00m
1 stop
ORD
SJU
14h 59m
1 stop
Depart: Tue Oct 17 2017 Return: Tue Oct 24 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
SJU
ORD
14h 03m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Sat Dec 9 2017 Return: Wed Dec 13 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 28m
1 stop
ORD
SJU
6h 55m
1 stop
Depart: Tue Sep 12 2017 Return: Mon Sep 18 2017 Trip spans 7 days
Frontier
Frontier
SJU
ORD
18h 00m
1 stop
ORD
SJU
17h 39m
1 stop
Depart: Thu Nov 9 2017 Return: Mon Nov 13 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
SJU
ORD
8h 28m
1 stop
ORD
SJU
12h 34m
1 stop
Depart: Wed Oct 25 2017 Return: Mon Oct 30 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
10h 45m
2 stops
MDW
SJU
6h 11m
1 stop
Depart: Thu Jan 11 2018 Return: Tue Jan 16 2018 Trip spans 6 days
Frontier
Frontier
SJU
ORD
18h 25m
1 stop
ORD
SJU
14h 30m
1 stop
Depart: Fri Oct 6 2017 Return: Wed Oct 11 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
BQN
ORD
7h 50m
1 stop
ORD
BQN
7h 33m
1 stop
Depart: Fri Dec 22 2017 Return: Wed Jan 3 2018 Trip spans 13 days
United
United
SJU
ORD
15h 04m
1 stop
ORD
SJU
10h 59m
1 stop
Depart: Thu Oct 12 2017 Return: Mon Oct 16 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
7h 15m
1 stop
MDW
SJU
6h 11m
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.

We compile tonnes of data for you
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

Aguadilla
$298
San Juan
$279
Ponce
$578
Destination

Chicago
only $279
only $389