Find Cheap Flights from Chicago O'Hare International to Caribbean

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Wed 2/21
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Book cheap flights from Chicago O'Hare International to Caribbean (round-trip)

Airports
Origin
Chicago
$189
only
$189
Destination
Aguadilla
$210
only
$210
Bridgetown
$345
only
$345
Nassau
$303
only
$303
San Juan
$189
only
$189
Havana
$242
only
$242
Tue, Apr 10
ORD
SJU
7h 31m
Mon, Apr 16
SJU
ORD
8h 38m
Trip: 7 days
Overall null null
Based on null reviews
Wed, Mar 7
ORD
BQN
6h 57m
Mon, Mar 12
BQN
ORD
9h 07m
Trip: 5 days
Overall null null
Based on null reviews
Tue, Mar 6
ORD
SJU
7h 01m
Mon, Apr 9
SJU
ORD
8h 38m
Trip: 34 days
Overall null null
Based on null reviews
Tue, Apr 10
ORD
HAV
9h 30m
Sun, Apr 22
HAV
ORD
10h 05m
Trip: 13 days
Overall null null
Based on null reviews
Tue, Apr 24
ORD
NAS
10h 04m
Tue, May 1
NAS
ORD
6h 15m
Trip: 8 days
Overall null null
Based on null reviews
Wed, Mar 14
ORD
BGI
10h 24m
Wed, Mar 21
BGI
ORD
9h 37m
Trip: 8 days
Overall null null
Based on null reviews
Wed, Mar 28
ORD
SJU
4h 45m
Tue, Apr 10
SJU
ORD
5h 10m
Trip: 14 days
Overall null null
Based on null reviews
Wed, Apr 11
ORD
SJU
7h 31m
Tue, Apr 17
SJU
ORD
8h 38m
Trip: 7 days
Overall null null
Based on null reviews
Tue, May 1
ORD
SJU
7h 32m
Mon, May 7
SJU
ORD
8h 26m
Trip: 7 days
Overall null null
Based on null reviews
Thu, Apr 19
ORD
BQN
8h 26m
Thu, Apr 26
BQN
ORD
9h 01m
Trip: 8 days
Overall null null
Based on null reviews
Tue, Apr 3
ORD
SJU
25h 53m
Mon, Apr 9
SJU
ORD
8h 38m
Trip: 7 days
Overall null null
Based on null reviews
Tue, May 8
ORD
SJU
7h 32m
Mon, May 14
SJU
ORD
8h 26m
Trip: 7 days
Overall null null
Based on null reviews
Fri, Apr 20
ORD
HAV
12h 30m
Sun, Apr 22
HAV
ORD
13h 10m
Trip: 3 days
Overall null null
Based on null reviews
Wed, May 16
ORD
SJU
7h 32m
Tue, May 22
SJU
ORD
8h 26m
Trip: 7 days
Overall null null
Based on null reviews
Mon, Feb 26
ORD
BQN
20h 07m
Thu, Mar 1
BQN
ORD
8h 39m
Trip: 4 days
Overall null null
Based on null reviews
Tue, May 1
ORD
HAV
9h 30m
Tue, May 8
HAV
ORD
10h 05m
Trip: 8 days
Overall null null
Based on null reviews
Fri, Apr 13
ORD
HAV
9h 30m
Tue, Apr 17
HAV
ORD
10h 20m
Trip: 5 days
Overall null null
Based on null reviews
Tue, Jun 5
ORD
SJU
7h 32m
Mon, Jun 11
SJU
ORD
8h 32m
Trip: 7 days
Overall null null
Based on null reviews
Mon, Jun 18
ORD
HAV
21h 25m
Sun, Jul 15
HAV
ORD
22h 01m
Trip: 28 days
Overall null null
Based on null reviews
Mon, Feb 26
ORD
SJU
17h 51m
Mon, Mar 5
SJU
ORD
32h 19m
Trip: 8 days
Overall null null
Based on null reviews

Chicago O'Hare International to Caribbean Flight Information

Flights Arrive in Caribbean
Flights Depart from Chicago O'Hare International
Flight Price $189
Airlines Frontier, Spirit Airlines, Copa Airlines, JetBlue, American Airlines, United
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

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