Find Deals on Flights from Caribbean to Chicago O'Hare International

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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Caribbean to Chicago O'Hare International

(Round-trip)
Depart: Thu Mar 2 2017 Return: Sun Mar 5 2017 Trip spans 4 days
JetBlue
JetBlue
SJU
ORD
9h 49m
1 stop
ORD
SJU
8h 28m
1 stop
Depart: Mon Mar 13 2017 Return: Mon Mar 20 2017 Trip spans 8 days
Major Airline
Major Airline
SJU
ORD
21h 53m
nonstop
ORD
SJU
12h 10m
nonstop
Depart: Sun Jan 15 2017 Return: Wed Jan 25 2017 Trip spans 11 days
Spirit Airlines
Spirit Airlines
SJU
ORD
13h 49m
1 stop
ORD
SJU
13h 39m
1 stop
Depart: Sat Jan 14 2017 Return: Mon Jan 16 2017 Trip spans 3 days
United
United
SJU
ORD
5h 05m
nonstop
ORD
SJU
4h 25m
nonstop
Depart: Fri May 12 2017 Return: Mon May 15 2017 Trip spans 4 days
American Airlines
American Airlines
SJU
ORD
5h 02m
nonstop
ORD
SJU
4h 55m
nonstop
Depart: Sun Jun 4 2017 Return: Fri Jun 16 2017 Trip spans 13 days
Delta
Delta
SJU
ORD
13h 19m
1 stop
ORD
SJU
16h 09m
2 stops
Depart: Fri Feb 3 2017 Return: Tue Feb 7 2017 Trip spans 5 days
JetBlue
JetBlue
SJU
ORD
9h 49m
1 stop
ORD
SJU
10h 19m
1 stop
Depart: Fri Jan 27 2017 Return: Mon Jan 30 2017 Trip spans 4 days
Major Airline
Major Airline
SJU
ORD
14h 42m
nonstop
ORD
SJU
10h 17m
nonstop
Depart: Wed Apr 5 2017 Return: Wed Apr 12 2017 Trip spans 8 days
JetBlue
JetBlue
SJU
ORD
27h 11m
1 stop
ORD
SJU
24h 09m
1 stop
Depart: Mon Dec 26 2016 Return: Tue Jan 3 2017 Trip spans 9 days
Air Canada
Air Canada
KIN
ORD
18h 45m
1 stop
ORD
KIN
16h 00m
1 stop
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: Tue Apr 4 2017 Return: Wed Apr 12 2017 Trip spans 9 days
JetBlue
JetBlue
SJU
ORD
9h 49m
1 stop
ORD
SJU
24h 09m
1 stop
Depart: Sat Dec 24 2016 Return: Sat Jan 14 2017 Trip spans 22 days
United
United
SJU
ORD
5h 00m
nonstop
ORD
SJU
4h 30m
nonstop
Depart: Tue Dec 20 2016 Return: Wed Jan 4 2017 Trip spans 16 days
Spirit Airlines
Spirit Airlines
STT
ORD
19h 55m
1 stop
ORD
STT
9h 12m
1 stop
Depart: Fri Apr 7 2017 Return: Sun Apr 16 2017 Trip spans 10 days
Frontier
Frontier
PUJ
ORD
5h 17m
nonstop
ORD
PUJ
4h 38m
nonstop
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: 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: Thu Jan 19 2017 Return: Sun Jan 22 2017 Trip spans 4 days
Major Airline
Major Airline
STT
ORD
7h 40m
1 stop
ORD
STT
9h 12m
1 stop
Depart: Wed Jun 14 2017 Return: Wed Jun 21 2017 Trip spans 8 days
American Airlines
American Airlines
SJU
ORD
5h 02m
nonstop
ORD
SJU
4h 55m
nonstop
Depart: Fri Feb 3 2017 Return: Sat Feb 4 2017 Trip spans 2 days
Major Airline
Major Airline
STT
ORD
7h 40m
1 stop
ORD
STT
9h 12m
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
$267
San Juan
$248
Saint Thomas Island
$326
Kingston
$577
Punta Cana
$654
Destination

Chicago
$248
Airlines Airline reviews

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

Overall
8.4
Boarding
8.1
Crew
8.2
Comfort
8.3
Food
7.7
Entertainment
7.7