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
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 Caribbean to Chicago O'Hare International

(Round-trip)
Depart: Tue Aug 29 2017 Return: Wed Aug 30 2017 Trip spans 2 days
American Airlines
American Airlines
KIN
ORD
11h 00m
2 stops
ORD
KIN
7h 16m
1 stop
Depart: Sat May 6 2017 Return: Sun May 7 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 42m
1 stop
ORD
SJU
6h 50m
1 stop
Depart: Fri Jun 2 2017 Return: Tue Jun 6 2017 Trip spans 5 days
Delta
Delta
NAS
ORD
15h 15m
1 stop
ORD
NAS
14h 06m
1 stop
Depart: Tue May 2 2017 Return: Wed May 3 2017 Trip spans 2 days
JetBlue
JetBlue
SJU
ORD
6h 56m
1 stop
ORD
SJU
6h 24m
1 stop
Depart: Wed May 24 2017 Return: Tue Jun 20 2017 Trip spans 28 days
United
United
NAS
ORD
4h 00m
nonstop
ORD
NAS
26h 44m
2 stops
Depart: Tue May 23 2017 Return: Mon Jun 5 2017 Trip spans 14 days
Air Canada
Air Canada
POS
ORD
18h 18m
1 stop
ORD
POS
18h 00m
2 stops
Depart: Thu May 11 2017 Return: Sat May 13 2017 Trip spans 3 days
Major Airline
Major Airline
KIN
ORD
8h 24m
1 stop
ORD
KIN
5h 43m
1 stop
Depart: Sat Sep 9 2017 Return: Fri Sep 15 2017 Trip spans 7 days
Aeromexico
Aeromexico
SDQ
ORD
28h 49m
1 stop
ORD
SDQ
22h 26m
1 stop
Depart: Thu Jul 27 2017 Return: Mon Jul 31 2017 Trip spans 5 days
Frontier
Frontier
PUJ
ORD
5h 10m
nonstop
ORD
PUJ
4h 47m
nonstop
Depart: Thu May 4 2017 Return: Tue May 9 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 42m
1 stop
ORD
SJU
6h 50m
1 stop
Depart: Thu Apr 27 2017 Return: Sun Apr 30 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 42m
1 stop
ORD
SJU
6h 50m
1 stop
Depart: Thu Apr 20 2017 Return: Mon Apr 24 2017 Trip spans 5 days
American Airlines
American Airlines
PUJ
ORD
8h 05m
1 stop
ORD
PUJ
12h 35m
1 stop
Depart: Wed Apr 26 2017 Return: Tue May 2 2017 Trip spans 7 days
United
United
BQN
ORD
8h 39m
1 stop
ORD
BQN
15h 30m
2 stops
Depart: Tue Jun 13 2017 Return: Mon Jun 19 2017 Trip spans 7 days
Air Canada
Air Canada
POS
ORD
18h 48m
2 stops
ORD
POS
17h 40m
1 stop
Depart: Thu Jul 6 2017 Return: Mon Jul 10 2017 Trip spans 5 days
Delta
Delta
NAS
ORD
6h 56m
1 stop
ORD
NAS
16h 28m
1 stop
Depart: Thu Apr 27 2017 Return: Mon May 1 2017 Trip spans 5 days
JetBlue
JetBlue
KIN
ORD
15h 20m
1 stop
ORD
KIN
23h 52m
1 stop
Depart: Fri Apr 28 2017 Return: Sun Apr 30 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 42m
1 stop
ORD
SJU
6h 50m
1 stop
Depart: Wed May 10 2017 Return: Sat May 13 2017 Trip spans 4 days
American Airlines
American Airlines
SJU
ORD
5h 20m
nonstop
ORD
SJU
4h 39m
nonstop
Depart: Thu Jun 8 2017 Return: Fri Jun 16 2017 Trip spans 9 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 45m
nonstop
Depart: Tue Aug 1 2017 Return: Tue Aug 15 2017 Trip spans 15 days
Major Airline
Major Airline
SJU
ORD
8h 19m
nonstop
ORD
SJU
11h 18m
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,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Aguadilla
$376
Santo Domingo
$429
Nassau
$348
San Juan
$296
Kingston
$222
Punta Cana
$366
Piarco
$369
Destination

Chicago
$222
Airlines Airline reviews

12 travelers who booked a flight from Kingston to Chicago rated their chosen airlines with an average of 7.6.

Overall
7.8
Boarding
7.0
Crew
7.7
Comfort
7.7
Food
7.8
Entertainment
7.8