Vacations from Chicago to Montego Bay
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Sky Beach Rooms
4/27/2025 April 27, 2025
- 5/03/2025 May 3, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $761 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 4 hours ago
5 night(s)
Sand And Tan
6/13/2025 June 13, 2025
- 6/18/2025 June 18, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,027 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Hotel Grand A View
6/13/2025 June 13, 2025
- 6/18/2025 June 18, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,033 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Grand Palladium Lady Hamilton Resort and Spa
9/18/2025 September 18, 2025
- 9/23/2025 September 23, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,055 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 12 hours ago
5 night(s)
Riu Negril
9/18/2025 September 18, 2025
- 9/23/2025 September 23, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,066 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 12 hours ago
5 night(s)
Iberostar Waves Rose Hall Beach
6/13/2025 June 13, 2025
- 6/18/2025 June 18, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,083 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Grand Palladium Jamaica Resort and Spa
9/18/2025 September 18, 2025
- 9/23/2025 September 23, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,126 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 12 hours ago
5 night(s)
Grand Decameron Cornwall Beach, All-Inclusive
6/13/2025 June 13, 2025
- 6/18/2025 June 18, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,136 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
6 night(s)
Hotel 39 Jamaica
4/27/2025 April 27, 2025
- 5/03/2025 May 3, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,142 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 4 hours ago
5 night(s)
Half Moon Jamaica
9/18/2025 September 18, 2025
- 9/23/2025 September 23, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,176 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 12 hours ago
5 night(s)
Riu Palace Tropical Bay
9/18/2025 September 18, 2025
- 9/23/2025 September 23, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,179 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 12 hours ago
6 night(s)
The Boardwalk Village Resor
4/27/2025 April 27, 2025
- 5/03/2025 May 3, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,203 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 4 hours ago
5 night(s)
Moon Palace Jamaica
6/13/2025 June 13, 2025
- 6/18/2025 June 18, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,215 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Riu Montego Bay
6/13/2025 June 13, 2025
- 6/18/2025 June 18, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,217 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Hyatt Ziva Rose Hall
9/18/2025 September 18, 2025
- 9/23/2025 September 23, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,226 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 12 hours ago
5 night(s)
Couples Tower Isle
6/13/2025 June 13, 2025
- 6/18/2025 June 18, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,243 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Riu Palace Aquarelle
9/18/2025 September 18, 2025
- 9/23/2025 September 23, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,245 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 12 hours ago
5 night(s)
Riu Ocho Rios
6/13/2025 June 13, 2025
- 6/18/2025 June 18, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,247 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Royalton Negril Resort and Spa
9/18/2025 September 18, 2025
- 9/23/2025 September 23, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,247 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 12 hours ago
5 night(s)
Riu Reggae
6/13/2025 June 13, 2025
- 6/18/2025 June 18, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,284 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Hyatt Zilara Rose Hall
9/18/2025 September 18, 2025
- 9/23/2025 September 23, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,308 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 12 hours ago
5 night(s)
Couples Sans Souci
9/18/2025 September 18, 2025
- 9/23/2025 September 23, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,357 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 12 hours ago
5 night(s)
Azul Beach Resort Negril by Karisma
6/13/2025 June 13, 2025
- 6/18/2025 June 18, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,369 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Princess Grand Jamaica
6/13/2025 June 13, 2025
- 6/18/2025 June 18, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,379 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Bahia Principe Luxury Runaway Bay
9/18/2025 September 18, 2025
- 9/23/2025 September 23, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,380 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 12 hours ago
5 night(s)
Sandals Ochi Beach Resort
9/18/2025 September 18, 2025
- 9/23/2025 September 23, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,408 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 12 hours ago
5 night(s)
Couples Negril
6/13/2025 June 13, 2025
- 6/18/2025 June 18, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,427 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
The Signature Level Grand Palladium Lady Hamilton
6/13/2025 June 13, 2025
- 6/18/2025 June 18, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,451 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Couples Swept Away
6/13/2025 June 13, 2025
- 6/18/2025 June 18, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,461 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 9 hours ago
5 night(s)
Zoetry Montego Bay Jamaica
9/18/2025 September 18, 2025
- 9/23/2025 September 23, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,479 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 12 hours ago
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*Average total price per person based on round trip flights in the Main Cabin and double occupancy hotel stays. Prices displayed have been collected within the last 24 hrs and may no longer be available at time of booking. Modifying this information may result in a different price. To find the most updated price, please visit aavacations.com.
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