Vacations from Chicago to Kingston
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Jamaica Palace
1/02/2026 January 2, 2026
- 1/09/2026 January 9, 2026
Chicago (ORD) To Kingston (KIN)
Flight + Hotel
from $1,476 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
R Hotel Kingston
1/02/2026 January 2, 2026
- 1/09/2026 January 9, 2026
Chicago (ORD) To Kingston (KIN)
Flight + Hotel
from $1,486 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Millsborough B&B
1/02/2026 January 2, 2026
- 1/09/2026 January 9, 2026
Chicago (ORD) To Kingston (KIN)
Flight + Hotel
from $1,550 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
ROK Hotel Kingston, Tapestry Collection by Hilton
1/02/2026 January 2, 2026
- 1/09/2026 January 9, 2026
Chicago (ORD) To Kingston (KIN)
Flight + Hotel
from $1,616 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Bahia Principe Luxury Runaway Bay
1/02/2026 January 2, 2026
- 1/09/2026 January 9, 2026
Chicago (ORD) To Kingston (KIN)
Flight + Hotel
from $2,172 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Sandals Ochi Beach Resort
1/02/2026 January 2, 2026
- 1/09/2026 January 9, 2026
Chicago (ORD) To Kingston (KIN)
Flight + Hotel
from $3,191 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Sandals Royal Plantation, Ocho Rios, Jamaica
1/02/2026 January 2, 2026
- 1/09/2026 January 9, 2026
Chicago (ORD) To Kingston (KIN)
Flight + Hotel
from $4,379 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 hours ago
7 night(s)
Pogas Suites
1/02/2026 January 2, 2026
- 1/09/2026 January 9, 2026
Chicago (ORD) To Kingston (KIN)
Flight + Hotel
from $41,199,210 * cmp-price-disclaimer
Per person based on 2-person occupancy Updated: 15 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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*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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