Flight + Hotel Packages from Chicago to Montego Bay
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Number of Stars
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1/30
4Night(s) Trip
Tamboo Resort
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ORD-MBJ
Flights+Hotel
From
$874* Price subject to change
Viewed:6 hours ago
2/30
4Night(s) Trip
Sky Beach Hotel
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ORD-MBJ
Flights+Hotel
From
$972* Price subject to change
Viewed:6 hours ago
3/30
4Night(s) Trip
Villas Sur Mer
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ORD-MBJ
Flights+Hotel
From
$995* Price subject to change
Viewed:6 hours ago
4/30
4Night(s) Trip
Hotel Rumbao, a Tribute Portfolio Hotel
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ORD-MBJ
Flights+Hotel
From
$1,218* Price subject to change
Viewed:12 hours ago
5/30
4Night(s) Trip
Hilton Garden Inn San Juan Condado
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ORD-MBJ
Flights+Hotel
From
$1,282* Price subject to change
Viewed:12 hours ago
6/30
4Night(s) Trip
Moon Palace Jamaica Grande - All Inclusive
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ORD-MBJ
Flights+Hotel
From
$1,285* Price subject to change
Viewed:6 hours ago
7/30
4Night(s) Trip
Doubletree By Hilton San Juan
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ORD-MBJ
Flights+Hotel
From
$1,292* Price subject to change
Viewed:12 hours ago
8/30
4Night(s) Trip
AC Hotel by Marriott San Juan Condado
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ORD-MBJ
Flights+Hotel
From
$1,299* Price subject to change
Viewed:12 hours ago
9/30
4Night(s) Trip
The Condado Plaza Hotel
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ORD-MBJ
Flights+Hotel
From
$1,308* Price subject to change
Viewed:12 hours ago
10/30
4Night(s) Trip
Royalton Negril, An Autograph Collection All-Inclusive Resort
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ORD-MBJ
Flights+Hotel
From
$1,313* Price subject to change
Viewed:6 hours ago
11/30
4Night(s) Trip
Grand Palladium Lady Hamilton Resort & Spa All Inclusive
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ORD-MBJ
Flights+Hotel
From
$1,322* Price subject to change
Viewed:6 hours ago
12/30
4Night(s) Trip
Sheraton Puerto Rico Resort & Casino
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ORD-MBJ
Flights+Hotel
From
$1,331* Price subject to change
Viewed:12 hours ago
13/30
4Night(s) Trip
Grand Palladium Jamaica Resort & Spa-All Inclusive
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ORD-MBJ
Flights+Hotel
From
$1,346* Price subject to change
Viewed:6 hours ago
14/30
4Night(s) Trip
Winslow's Bungalows - Key West Historic Inns
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ORD-MBJ
Flights+Hotel
From
$1,362* Price subject to change
Viewed:12 hours ago
15/30
4Night(s) Trip
Blue Flamingo Resort Key West
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ORD-MBJ
Flights+Hotel
From
$1,369* Price subject to change
Viewed:12 hours ago
16/30
4Night(s) Trip
Parrot Key Hotel And Resort
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ORD-MBJ
Flights+Hotel
From
$1,384* Price subject to change
Viewed:12 hours ago
17/30
4Night(s) Trip
Oceans Edge Key West
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ORD-MBJ
Flights+Hotel
From
$1,389* Price subject to change
Viewed:12 hours ago
18/30
4Night(s) Trip
The Signature Level at Grand Palladium Lady Hamilton Resort & Spa- All Inclusive
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ORD-MBJ
Flights+Hotel
From
$1,408* Price subject to change
Viewed:6 hours ago
19/30
4Night(s) Trip
Riu Reggae - Adults Only - All Inclusive
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ORD-MBJ
Flights+Hotel
From
$1,431* Price subject to change
Viewed:6 hours ago
20/30
4Night(s) Trip
The Perry Hotel Key West
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ORD-MBJ
Flights+Hotel
From
$1,437* Price subject to change
Viewed:12 hours ago
21/30
4Night(s) Trip
Riu Palace Tropical Bay-All Inclusive
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ORD-MBJ
Flights+Hotel
From
$1,457* Price subject to change
Viewed:6 hours ago
22/30
4Night(s) Trip
O:live Boutique Hotel
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ORD-MBJ
Flights+Hotel
From
$1,461* Price subject to change
Viewed:12 hours ago
23/30
4Night(s) Trip
Azul Beach Resort Negril, Gourmet All Inclusive by Karisma
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ORD-MBJ
Flights+Hotel
From
$1,465* Price subject to change
Viewed:6 hours ago
24/30
4Night(s) Trip
Margaritaville Beach House Key West
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ORD-MBJ
Flights+Hotel
From
$1,482* Price subject to change
Viewed:12 hours ago
25/30
4Night(s) Trip
La Concha Key West, Autograph Collection
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ORD-MBJ
Flights+Hotel
From
$1,484* Price subject to change
Viewed:12 hours ago
26/30
4Night(s) Trip
The Cliff Hotel
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ORD-MBJ
Flights+Hotel
From
$1,264* Price subject to change
Viewed:a day ago
27/30
4Night(s) Trip
Couples Swept Away - All Inclusive - Couples Only
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ORD-MBJ
Flights+Hotel
From
$1,436* Price subject to change
Viewed:a day ago
28/30
4Night(s) Trip
Couples Negril - All Inclusive - Couples Only
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ORD-MBJ
Flights+Hotel
From
$1,440* Price subject to change
Viewed:a day ago
29/30
4Night(s) Trip
Castlevue B&B
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ORD-MBJ
Flights+Hotel
From
$847* Price subject to change
Viewed:a day ago
30/30
4Night(s) Trip
Chaudhry Second Floor Single Suite
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ORD-MBJ
Flights+Hotel
From
$884* Price subject to change
Viewed:a day ago
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*Average total price per person based on round trip flights and double occupancy hotel stays. Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply.
Current Weather in Montego Bay
Tuesdayovercast clouds
89°F06/03/25
Wednesdaylight rain
86°F06/04/25
Thursdaylight rain
85°F06/05/25
Fridaymoderate rain
84°F06/06/25
Saturdaylight rain
85°F06/07/25
Sundaylight rain
85°F06/08/25
Mondaylight rain
83°F06/09/25
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