Find Cheap Flights from Chicago to Caribbean

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Sat 12/16
Sat 12/23
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Book cheap flights from Chicago to Caribbean (round-trip)

Airports
Origin
Chicago
$260
only
$260
Destination
San Juan
$260
only
$260
Havana
$272
only
$272
Tue, Feb 13
ORD
SJU
14h 17m
Thu, Feb 22
SJU
ORD
16h 17m
Trip: 10 days
Overall null null
Based on null reviews
Sat, Jan 20
ORD
HAV
22h 00m
Mon, Mar 5
HAV
ORD
19h 20m
Trip: 45 days
Overall null null
Based on null reviews
Tue, Jan 23
ORD
HAV
5h 45m
Wed, Feb 7
HAV
ORD
9h 01m
Trip: 16 days
Overall null null
Based on null reviews
Mon, Mar 19
ORD
HAV
10h 45m
Fri, Mar 23
HAV
ORD
9h 07m
Trip: 5 days
Overall null null
Based on null reviews
Wed, Jan 17
ORD
SJU
6h 57m
Wed, Jan 24
SJU
ORD
8h 14m
Trip: 8 days
Overall null null
Based on null reviews
Fri, Jan 5
ORD
HAV
18h 20m
Fri, Jan 26
HAV
ORD
10h 15m
Trip: 22 days
Overall null null
Based on null reviews
Wed, Jan 17
ORD
SJU
6h 57m
Tue, Jan 23
SJU
ORD
24h 55m
Trip: 7 days
Overall null null
Based on null reviews
Mon, Jan 29
ORD
HAV
5h 45m
Tue, Feb 6
HAV
ORD
9h 01m
Trip: 9 days
Overall null null
Based on null reviews
Sun, Apr 1
ORD
HAV
10h 40m
Thu, Apr 5
HAV
ORD
12h 32m
Trip: 5 days
Overall null null
Based on null reviews
Sat, Jan 20
ORD
SJU
6h 57m
Wed, Jan 24
SJU
ORD
8h 14m
Trip: 5 days
Overall null null
Based on null reviews
Fri, Jan 12
ORD
HAV
16h 15m
Sun, Jan 21
HAV
ORD
10h 05m
Trip: 10 days
Overall null null
Based on null reviews
Sat, Jan 20
ORD
SJU
6h 57m
Tue, Jan 23
SJU
ORD
24h 55m
Trip: 4 days
Overall null null
Based on null reviews
Thu, Feb 1
ORD
HAV
5h 45m
Wed, Feb 7
HAV
ORD
9h 01m
Trip: 7 days
Overall null null
Based on null reviews
Mon, Apr 2
ORD
HAV
8h 45m
Thu, Apr 5
HAV
ORD
12h 32m
Trip: 4 days
Overall null null
Based on null reviews
Wed, Jan 17
ORD
HAV
18h 20m
Tue, Jan 30
HAV
ORD
11h 45m
Trip: 14 days
Overall null null
Based on null reviews
Mon, Jan 15
ORD
SJU
22h 25m
Tue, Jan 23
SJU
ORD
24h 55m
Trip: 9 days
Overall null null
Based on null reviews
Sun, Feb 4
ORD
HAV
5h 45m
Wed, Feb 7
HAV
ORD
9h 01m
Trip: 4 days
Overall null null
Based on null reviews
Sat, Jan 27
ORD
HAV
18h 20m
Sun, Feb 4
HAV
ORD
11h 44m
Trip: 9 days
Overall null null
Based on null reviews
Mon, Jan 15
ORD
SJU
22h 25m
Tue, Jan 23
SJU
ORD
24h 55m
Trip: 9 days
Overall null null
Based on null reviews
Tue, Feb 6
ORD
HAV
5h 45m
Tue, Feb 20
HAV
ORD
9h 58m
Trip: 15 days
Overall null null
Based on null reviews
*
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