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: Fri Mar 2 2018 Return: Wed Mar 7 2018 Trip spans 6 days
Spirit Airlines
Spirit Airlines
BQN
ORD
8h 41m
1 stop
ORD
BQN
7h 03m
1 stop
Depart: Thu Jan 25 2018 Return: Mon Jan 29 2018 Trip spans 5 days
Multiple Airlines
Multiple Airlines
SJU
ORD
15h 59m
2 stops
ORD
SJU
15h 32m
1 stop
Depart: Mon Oct 23 2017 Return: Fri Oct 27 2017 Trip spans 5 days
Delta
Delta
SJU
ORD
7h 14m
1 stop
ORD
SJU
9h 00m
1 stop
Depart: Thu Jan 25 2018 Return: Tue Jan 30 2018 Trip spans 6 days
JetBlue
JetBlue
SJU
ORD
10h 41m
1 stop
ORD
SJU
6h 46m
1 stop
Depart: Thu Dec 7 2017 Return: Sun Dec 10 2017 Trip spans 4 days
United
United
SJU
ORD
8h 24m
1 stop
ORD
SJU
13h 00m
1 stop
Depart: Fri Nov 17 2017 Return: Mon Nov 20 2017 Trip spans 4 days
American Airlines
American Airlines
SJU
ORD
5h 27m
nonstop
ORD
SJU
4h 33m
nonstop
Depart: Mon Mar 12 2018 Return: Tue Mar 20 2018 Trip spans 9 days
Spirit Airlines
Spirit Airlines
BQN
ORD
8h 43m
1 stop
ORD
BQN
7h 03m
1 stop
Depart: Tue Mar 13 2018 Return: Tue Mar 20 2018 Trip spans 8 days
Spirit Airlines
Spirit Airlines
BQN
ORD
8h 43m
1 stop
ORD
BQN
7h 03m
1 stop
Depart: Fri Dec 1 2017 Return: Wed Dec 6 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
32h 28m
1 stop
ORD
SJU
17h 52m
1 stop
Depart: Fri Jan 26 2018 Return: Mon Jan 29 2018 Trip spans 4 days
Multiple Airlines
Multiple Airlines
SJU
ORD
12h 51m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Wed Jan 24 2018 Return: Tue Jan 30 2018 Trip spans 7 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 13m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Fri Jan 26 2018 Return: Tue Jan 30 2018 Trip spans 5 days
JetBlue
JetBlue
SJU
ORD
10h 41m
1 stop
ORD
SJU
6h 46m
1 stop
Depart: Thu Feb 1 2018 Return: Mon Feb 5 2018 Trip spans 5 days
Multiple Airlines
Multiple Airlines
SJU
ORD
8h 13m
1 stop
ORD
SJU
11h 29m
1 stop
Depart: Sat Jan 27 2018 Return: Sun Jan 28 2018 Trip spans 2 days
JetBlue
JetBlue
SJU
ORD
10h 41m
1 stop
ORD
SJU
6h 46m
1 stop
Depart: Thu Nov 16 2017 Return: Wed Nov 29 2017 Trip spans 14 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 28m
1 stop
ORD
SJU
17h 52m
1 stop
Depart: Wed Jan 24 2018 Return: Sun Jan 28 2018 Trip spans 5 days
Multiple Airlines
Multiple Airlines
SJU
ORD
8h 13m
1 stop
ORD
SJU
7h 17m
1 stop
Depart: Wed Nov 29 2017 Return: Mon Dec 4 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
6h 45m
1 stop
MDW
SJU
7h 50m
1 stop
Depart: Wed Nov 22 2017 Return: Mon Nov 27 2017 Trip spans 6 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
14h 58m
1 stop
Depart: Fri Dec 22 2017 Return: Wed Jan 3 2018 Trip spans 13 days
American Airlines
American Airlines
SJU
ORD
5h 29m
nonstop
ORD
SJU
4h 33m
nonstop
Depart: Wed Nov 29 2017 Return: Mon Dec 4 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
32h 28m
1 stop
ORD
SJU
17h 52m
1 stop
* 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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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
$195
San Juan
$216
Destination

Chicago
only $195
only $382
Airlines Airline reviews

59 travelers who booked a flight from Aguadilla to Chicago rated their chosen airlines with an average of 7.8.

Overall
8.2
Boarding
8.1
Crew
8.3
Comfort
8.0
Food
7.3
Entertainment
7.2