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
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: Mon Jun 5 2017 Return: Wed Jun 21 2017 Trip spans 17 days
Spirit Airlines
Spirit Airlines
BQN
ORD
8h 28m
1 stop
ORD
BQN
8h 00m
1 stop
Depart: Tue May 9 2017 Return: Tue May 23 2017 Trip spans 15 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 45m
nonstop
Depart: Thu May 11 2017 Return: Tue May 16 2017 Trip spans 6 days
American Airlines
American Airlines
SJU
ORD
5h 20m
nonstop
ORD
SJU
4h 34m
nonstop
Depart: Wed Apr 5 2017 Return: Tue Apr 11 2017 Trip spans 7 days
Delta
Delta
SJU
MDW
7h 18m
1 stop
MDW
SJU
7h 50m
1 stop
Depart: Tue Mar 21 2017 Return: Tue Mar 28 2017 Trip spans 8 days
Major Airline
Major Airline
SJU
ORD
9h 01m
nonstop
ORD
SJU
7h 10m
nonstop
Depart: Fri Aug 18 2017 Return: Mon Aug 21 2017 Trip spans 4 days
JetBlue
JetBlue
SJU
ORD
6h 43m
nonstop
ORD
SJU
6h 37m
nonstop
Depart: Wed Apr 26 2017 Return: Fri Apr 28 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
SJU
ORD
7h 29m
1 stop
ORD
SJU
6h 50m
1 stop
Depart: Fri May 12 2017 Return: Sun May 14 2017 Trip spans 3 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 45m
nonstop
Depart: Tue May 9 2017 Return: Tue May 16 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 42m
1 stop
ORD
SJU
6h 50m
1 stop
Depart: Wed Apr 12 2017 Return: Wed Apr 26 2017 Trip spans 15 days
Delta
Delta
SJU
MDW
7h 40m
1 stop
MDW
SJU
8h 09m
1 stop
Depart: Tue Mar 28 2017 Return: Mon Apr 3 2017 Trip spans 7 days
Major Airline
Major Airline
SJU
ORD
15h 11m
nonstop
ORD
SJU
24h 08m
nonstop
Depart: Tue Aug 15 2017 Return: Sun Aug 20 2017 Trip spans 6 days
American Airlines
American Airlines
SJU
ORD
5h 02m
nonstop
ORD
SJU
4h 55m
nonstop
Depart: Wed Apr 26 2017 Return: Fri Apr 28 2017 Trip spans 3 days
Delta
Delta
SJU
MDW
7h 40m
1 stop
MDW
SJU
6h 25m
1 stop
Depart: Thu Jun 22 2017 Return: Thu Jul 6 2017 Trip spans 15 days
JetBlue
JetBlue
SJU
ORD
6h 43m
nonstop
ORD
SJU
6h 37m
nonstop
Depart: Wed Apr 12 2017 Return: Tue Apr 25 2017 Trip spans 14 days
Major Airline
Major Airline
SJU
ORD
15h 11m
nonstop
ORD
SJU
6h 43m
nonstop
Depart: Fri May 12 2017 Return: Mon May 15 2017 Trip spans 4 days
Delta
Delta
SJU
MDW
8h 24m
1 stop
MDW
SJU
6h 49m
1 stop
Depart: Mon Jul 24 2017 Return: Wed Aug 9 2017 Trip spans 17 days
Spirit Airlines
Spirit Airlines
BQN
ORD
8h 27m
1 stop
ORD
BQN
8h 00m
1 stop
Depart: Thu Jul 13 2017 Return: Thu Jul 20 2017 Trip spans 8 days
JetBlue
JetBlue
SJU
ORD
6h 43m
1 stop
ORD
SJU
9h 07m
1 stop
Depart: Thu Jun 1 2017 Return: Mon Jun 12 2017 Trip spans 12 days
Major Airline
Major Airline
SJU
ORD
12h 39m
nonstop
ORD
SJU
6h 26m
nonstop
Depart: Wed Jul 12 2017 Return: Wed Jul 19 2017 Trip spans 8 days
Delta
Delta
SJU
MDW
9h 39m
1 stop
MDW
SJU
6h 54m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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
$323
San Juan
$328
Destination

Chicago
only $323
only $362
Airlines Airline reviews

37 travelers who booked a flight from Aguadilla to Chicago rated their chosen airlines with an average of 8.1.

Overall
8.5
Boarding
8.3
Crew
8.4
Comfort
8.4
Food
7.4
Entertainment
7.8