Vacations from Chicago to Montego Bay
Explore our popular vacation packages from Charlotte From - To
From cmp-location-selector-label-description-origin
To cmp-location-selector-label-description-destination
Close
5-7 nights
Choose your night stays Any number of nights
Close
Advanced
Choose your night stays Choose your night stays
Close
Clear
cmp-carousel-container-explain 6 night(s)
Sky Beach Rooms
12/09/2025 December 9, 2025
- 12/15/2025 December 15, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $763 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 4 hours ago
6 night(s)
Iberostar Waves Rose Hall Beach
12/09/2025 December 9, 2025
- 12/15/2025 December 15, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,275 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 4 hours ago
6 night(s)
Secrets St. James
12/09/2025 December 9, 2025
- 12/15/2025 December 15, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,747 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: an hour ago
6 night(s)
Secrets Wild Orchid Montego Bay
12/09/2025 December 9, 2025
- 12/15/2025 December 15, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,999 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: an hour ago
7 night(s)
Iberostar Waves Rose Hall Beach
1/14/2026 January 14, 2026
- 1/21/2026 January 21, 2026
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,741 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
5 night(s)
Secrets St. James
12/30/2025 December 30, 2025
- 1/04/2026 January 4, 2026
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $2,499 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 4 hours ago
5 night(s)
Secrets Wild Orchid Montego Bay
12/30/2025 December 30, 2025
- 1/04/2026 January 4, 2026
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $2,505 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 4 hours ago
5 night(s)
Iberostar Waves Rose Hall Beach
12/30/2025 December 30, 2025
- 1/04/2026 January 4, 2026
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,964 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 4 hours ago
7 night(s)
Secrets St. James
1/14/2026 January 14, 2026
- 1/21/2026 January 21, 2026
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $2,655 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
7 night(s)
Secrets Wild Orchid Montego Bay
1/30/2026 January 30, 2026
- 2/06/2026 February 6, 2026
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $2,974 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 6 hours ago
7 night(s)
Secrets St. James
1/30/2026 January 30, 2026
- 2/06/2026 February 6, 2026
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $2,727 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 6 hours ago
7 night(s)
Secrets Wild Orchid Montego Bay
1/14/2026 January 14, 2026
- 1/21/2026 January 21, 2026
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $3,006 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 3 hours ago
7 night(s)
Iberostar Waves Rose Hall Beach
9/23/2025 September 23, 2025
- 9/30/2025 September 30, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,660 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Secrets St. James
9/23/2025 September 23, 2025
- 9/30/2025 September 30, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $2,150 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Secrets Wild Orchid Montego Bay
9/23/2025 September 23, 2025
- 9/30/2025 September 30, 2025
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $2,397 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 20 hours ago
7 night(s)
Iberostar Waves Rose Hall Beach
8/02/2026 August 2, 2026
- 8/09/2026 August 9, 2026
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $1,835 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 23 hours ago
7 night(s)
Secrets St. James
8/02/2026 August 2, 2026
- 8/09/2026 August 9, 2026
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $2,517 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 23 hours ago
7 night(s)
Secrets Wild Orchid Montego Bay
8/02/2026 August 2, 2026
- 8/09/2026 August 9, 2026
Chicago (ORD) To Montego Bay (MBJ)
Flight + Hotel
from $2,535 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 23 hours ago
*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.
Powered by: OpenWeatherMap.org