Find Cheap Flights from Chicago Midway to Caribbean

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Book cheap flights from Chicago Midway to Caribbean (round-trip)

Airports
Origin
Chicago
$280
only
$280
Destination
San Juan
$349
only
$349
Saint Thomas Island
$348
only
$348
Havana
$280
only
$280
Fri, Feb 23
MDW
HAV
6h 35m
Wed, Feb 28
HAV
MDW
7h 50m
Trip: 6 days
Overall null null
Based on null reviews
Wed, Mar 14
MDW
SJU
12h 55m
Tue, Apr 3
SJU
MDW
14h 34m
Trip: 21 days
Overall null null
Based on null reviews
Mon, Mar 5
MDW
HAV
6h 35m
Mon, Mar 12
HAV
MDW
9h 18m
Trip: 7 days
Overall null null
Based on null reviews
Sat, Feb 10
MDW
HAV
16h 40m
Thu, Feb 15
HAV
MDW
7h 50m
Trip: 6 days
Overall null null
Based on null reviews
Mon, May 14
MDW
HAV
16h 55m
Wed, May 23
HAV
MDW
12h 33m
Trip: 10 days
Overall null null
Based on null reviews
Tue, Jun 5
MDW
SJU
8h 44m
Tue, Jun 19
SJU
MDW
19h 36m
Trip: 15 days
Overall null null
Based on null reviews
Mon, Mar 5
MDW
HAV
6h 35m
Tue, Mar 20
HAV
MDW
9h 18m
Trip: 15 days
Overall null null
Based on null reviews
Tue, Mar 20
MDW
HAV
6h 35m
Tue, Mar 27
HAV
MDW
19h 07m
Trip: 8 days
Overall null null
Based on null reviews
Mon, May 14
MDW
HAV
15h 21m
Wed, May 16
HAV
MDW
10h 17m
Trip: 3 days
Overall null null
Based on null reviews
Wed, Feb 21
MDW
HAV
6h 35m
Sat, Feb 24
HAV
MDW
7h 49m
Trip: 4 days
Overall null null
Based on null reviews
Sun, Jun 3
MDW
HAV
6h 35m
Wed, Jun 6
HAV
MDW
9h 18m
Trip: 4 days
Overall null null
Based on null reviews
Wed, Mar 7
MDW
HAV
6h 35m
Wed, Mar 14
HAV
MDW
9h 18m
Trip: 7 days
Overall null null
Based on null reviews
Wed, May 2
MDW
HAV
6h 35m
Sun, May 6
HAV
MDW
9h 18m
Trip: 5 days
Overall null null
Based on null reviews
Sun, Apr 22
MDW
HAV
17h 20m
Tue, Apr 24
HAV
MDW
9h 18m
Trip: 3 days
Overall null null
Based on null reviews
Thu, Feb 8
MDW
HAV
6h 35m
Fri, Feb 9
HAV
MDW
7h 50m
Trip: 2 days
Overall null null
Based on null reviews
Mon, Mar 12
MDW
HAV
6h 35m
Tue, Mar 13
HAV
MDW
9h 18m
Trip: 2 days
Overall null null
Based on null reviews
Tue, Apr 3
MDW
HAV
6h 35m
Thu, Apr 5
HAV
MDW
9h 18m
Trip: 3 days
Overall null null
Based on null reviews
Fri, Feb 23
MDW
HAV
6h 35m
Tue, Feb 27
HAV
MDW
7h 50m
Trip: 5 days
Overall null null
Based on null reviews
Thu, May 10
MDW
HAV
5h 05m
Sun, May 13
HAV
MDW
8h 52m
Trip: 4 days
Overall null null
Based on null reviews
Tue, Apr 17
MDW
STT
6h 27m
Mon, Apr 23
STT
MDW
9h 26m
Trip: 7 days
Overall null null
Based on null reviews

Chicago Midway to Caribbean Flight Information

Flights Arrive in Caribbean
Flights Depart from Chicago Midway
Flight Price $280
Airlines Delta
*
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