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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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 Aug 16 2017 Return: Tue Aug 22 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 16m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Thu Sep 28 2017 Return: Sun Oct 1 2017 Trip spans 4 days
Delta
Delta
SJU
MDW
7h 29m
1 stop
MDW
SJU
6h 54m
1 stop
Depart: Fri Oct 6 2017 Return: Thu Oct 12 2017 Trip spans 7 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 45m
nonstop
Depart: Tue Jul 4 2017 Return: Sun Jul 9 2017 Trip spans 6 days
Major Airline
Major Airline
SJU
ORD
12h 49m
1 stop
ORD
SJU
9h 07m
1 stop
Depart: Fri May 12 2017 Return: Wed May 17 2017 Trip spans 6 days
American Airlines
American Airlines
SJU
ORD
5h 20m
nonstop
ORD
SJU
9h 06m
1 stop
Depart: Mon Sep 4 2017 Return: Tue Sep 12 2017 Trip spans 9 days
JetBlue
JetBlue
BQN
ORD
19h 52m
1 stop
ORD
BQN
15h 19m
1 stop
Depart: Wed Aug 30 2017 Return: Wed Sep 6 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 16m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Wed Oct 4 2017 Return: Tue Oct 10 2017 Trip spans 7 days
Delta
Delta
SJU
MDW
8h 57m
1 stop
MDW
SJU
6h 32m
1 stop
Depart: Thu Sep 28 2017 Return: Sun Oct 1 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 36m
1 stop
ORD
SJU
6h 51m
1 stop
Depart: Mon Jul 10 2017 Return: Fri Jul 14 2017 Trip spans 5 days
United
United
SJU
ORD
7h 43m
1 stop
ORD
SJU
4h 45m
nonstop
Depart: Tue Jun 6 2017 Return: Tue Jun 27 2017 Trip spans 22 days
American Airlines
American Airlines
SJU
ORD
9h 55m
1 stop
ORD
SJU
7h 45m
1 stop
Depart: Thu Oct 12 2017 Return: Mon Oct 16 2017 Trip spans 5 days
Delta
Delta
SJU
MDW
9h 39m
1 stop
MDW
SJU
6h 54m
1 stop
Depart: Fri Sep 29 2017 Return: Wed Oct 4 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 36m
1 stop
ORD
SJU
6h 51m
1 stop
Depart: Wed Oct 18 2017 Return: Mon Oct 23 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 36m
1 stop
ORD
SJU
6h 51m
1 stop
Depart: Fri Jul 7 2017 Return: Sun Jul 9 2017 Trip spans 3 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 45m
nonstop
Depart: Wed May 24 2017 Return: Wed May 31 2017 Trip spans 8 days
American Airlines
American Airlines
SJU
ORD
8h 13m
1 stop
ORD
SJU
9h 39m
1 stop
Depart: Tue Jun 13 2017 Return: Wed Jun 28 2017 Trip spans 16 days
JetBlue
JetBlue
BQN
ORD
20h 00m
1 stop
ORD
BQN
18h 19m
1 stop
Depart: Fri Oct 20 2017 Return: Wed Oct 25 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 36m
1 stop
ORD
SJU
6h 51m
1 stop
Depart: Thu Jul 13 2017 Return: Mon Jul 31 2017 Trip spans 19 days
Major Airline
Major Airline
SJU
ORD
12h 42m
nonstop
ORD
SJU
11h 18m
nonstop
Depart: Mon Jul 10 2017 Return: Fri Jul 14 2017 Trip spans 5 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 45m
nonstop
* 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
$389
San Juan
$336
Destination

Chicago
only $336
only $362
Airlines Airline reviews

38 travelers who booked a flight from San Juan to Chicago rated their chosen airlines with an average of 8.0.

Overall
8.4
Boarding
8.2
Crew
8.4
Comfort
8.2
Food
7.3
Entertainment
7.6