Find Deals on 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
Students
under 26
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Puerto Rico to Chicago

(Round-trip)
Depart: Wed Jan 11 2017 Return: Wed Jan 18 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
SJU
ORD
7h 16m
1 stop
ORD
SJU
6h 53m
1 stop
Depart: Mon Apr 24 2017 Return: Sun Apr 30 2017 Trip spans 7 days
JetBlue
JetBlue
BQN
ORD
20h 47m
1 stop
ORD
BQN
18h 11m
1 stop
Depart: Sat Dec 24 2016 Return: Sat Dec 31 2016 Trip spans 8 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 35m
nonstop
Depart: Fri Feb 10 2017 Return: Mon Feb 13 2017 Trip spans 4 days
American Airlines
American Airlines
SJU
ORD
5h 27m
nonstop
ORD
SJU
4h 30m
nonstop
Depart: Fri Feb 3 2017 Return: Sun Feb 5 2017 Trip spans 3 days
Delta
Delta
SJU
MDW
17h 06m
2 stops
MDW
SJU
8h 14m
1 stop
Depart: Tue Jan 24 2017 Return: Mon Jan 30 2017 Trip spans 7 days
Major Airline
Major Airline
SJU
ORD
7h 16m
nonstop
ORD
SJU
6h 53m
nonstop
Depart: Wed Feb 1 2017 Return: Wed Feb 8 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
SJU
ORD
12h 07m
1 stop
ORD
SJU
12h 29m
1 stop
Depart: Mon May 15 2017 Return: Sat May 20 2017 Trip spans 6 days
JetBlue
JetBlue
BQN
ORD
27h 44m
1 stop
ORD
BQN
18h 51m
1 stop
Depart: Tue Dec 6 2016 Return: Sun Dec 11 2016 Trip spans 6 days
Spirit Airlines
Spirit Airlines
BQN
ORD
8h 53m
1 stop
ORD
BQN
6h 52m
1 stop
Depart: Sun Dec 25 2016 Return: Sat Dec 31 2016 Trip spans 7 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 35m
nonstop
Depart: Wed Mar 15 2017 Return: Tue Mar 21 2017 Trip spans 7 days
American Airlines
American Airlines
SJU
ORD
5h 02m
nonstop
ORD
SJU
4h 55m
nonstop
Depart: Thu Dec 8 2016 Return: Tue Jan 17 2017 Trip spans 41 days
Delta
Delta
SJU
MDW
7h 36m
1 stop
MDW
SJU
13h 15m
2 stops
Depart: Mon Feb 13 2017 Return: Tue Feb 21 2017 Trip spans 9 days
United
United
SJU
ORD
9h 59m
1 stop
ORD
SJU
4h 25m
nonstop
Depart: Thu Apr 27 2017 Return: Sun Apr 30 2017 Trip spans 4 days
American Airlines
American Airlines
SJU
ORD
5h 02m
nonstop
ORD
SJU
4h 55m
nonstop
Depart: Fri Jan 13 2017 Return: Tue Jan 17 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJU
ORD
13h 49m
1 stop
ORD
SJU
12h 29m
1 stop
Depart: Mon May 15 2017 Return: Sun May 21 2017 Trip spans 7 days
Major Airline
Major Airline
SJU
ORD
12h 30m
nonstop
ORD
SJU
8h 21m
nonstop
Depart: Thu Jun 1 2017 Return: Wed Jun 7 2017 Trip spans 7 days
American Airlines
American Airlines
SJU
ORD
5h 02m
nonstop
ORD
SJU
4h 55m
nonstop
Depart: Wed Jan 18 2017 Return: Fri Jan 20 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
SJU
ORD
12h 07m
1 stop
ORD
SJU
13h 39m
1 stop
Depart: Tue Apr 4 2017 Return: Wed Apr 12 2017 Trip spans 9 days
Delta
Delta
SJU
MDW
6h 48m
1 stop
MDW
SJU
16h 39m
2 stops
Depart: Tue May 16 2017 Return: Tue May 30 2017 Trip spans 15 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 50m
nonstop
* 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
$267
San Juan
$196
Destination

Chicago
only $196
only $310
Airlines Airline reviews

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

Overall
8.4
Boarding
8.3
Crew
8.3
Comfort
8.3
Food
7.5
Entertainment
7.5