Search 24 Chicago to Saint James Resort Vacation Deals and 21 Resorts

At CheapCaribbean.com, we’ve created 24 custom vacation packages for 21 different resorts in Saint James. Each “Flight + Hotel” package is priced per person. Each “Hotel Only” package is priced per night. Make sure to use the filters to find the perfect Saint James resort deal for you!
× Amenities
× Class
× Theme
FLIGHT + HOTEL
Half Moon Jamaica - All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $1,884 to $2,910* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Breathless Montego Bay Resort & Spa - All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $1,059 to $1,625* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Zoëtry Montego Bay Jamaica - All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $877 to $1,198* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Iberostar Grand Rose Hall - All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $855 to $1,191* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Riu Reggae - AIl Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $821 to $1,130* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Iberostar Selection Rose Hall Suites - All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $804 to $1,106* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Hideaway at Royalton Blue Waters, An Autograph Collection- All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $779 to $1,064* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Ocean Eden Bay Resort - All inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $728 to $987* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Iberostar Rose Hall Beach - All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $695 to $924* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Ocean Coral Spring - All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $670 to $900* /person
3 to 5 Day Trips - Aug to Nov

Top Saint James Destination: Montego Bay Resort Packages from Chicago

Offering an astounding 20 vacation packages from Chicago to a top city in Saint James, CheapCaribbean.com offers a vacation package to Montego Bay that's just right for everyone, with amenities including a spa, a golf and an exercise gym. Whether you're seeking dining, romance or on the beach-focused experiences, our vacation packages have you covered. These enticing deals, priced per person, include your flight and stay at top-notch hotels from esteemed brands such as Iberostar Hotels & Resorts, Ocean by H10 and Hyatt Inclusive Collection. The packages range form $670 to $2,910, with an average price per person at $917, providing unbeatable value for a 3-day getaway in Montego Bay.*

FLIGHT + HOTEL
Ocean Coral Spring - All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $670 to $900* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Iberostar Rose Hall Beach - All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $695 to $924* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Ocean Eden Bay Resort - All inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $728 to $987* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Hideaway at Royalton Blue Waters, An Autograph Collection- All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $779 to $1,064* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Iberostar Selection Rose Hall Suites - All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $804 to $1,106* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Riu Reggae - AIl Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $821 to $1,130* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Iberostar Grand Rose Hall - All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $855 to $1,191* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Zoëtry Montego Bay Jamaica - All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $877 to $1,198* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Breathless Montego Bay Resort & Spa - All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $1,059 to $1,625* /person
3 to 5 Day Trips - Aug to Nov
FLIGHT + HOTEL
Half Moon Jamaica - All Inclusive Montego Bay
All-Inclusive
2 Deals Available!
From $1,884 to $2,910* /person
3 to 5 Day Trips - Aug to Nov
Silent Waters Villa Montego Bay
Silent Waters Villa
Montego Bay
Property Location: Located in Montego Bay, this villa is in the mountains, within a 15-minute drive of Fairview Shopping Center and Tryall Golf Club. This 5-star villa is 17 mi (27.3 km) from Rose Ha...
Round Hill Hotel And Villas Montego Bay
Property Location: Located in Montego Bay, Round Hill Hotel And Villas is by the ocean, within a 10-minute drive of Jamaica Beaches and Tryall Golf Club. This 4.5-star hotel is 8.7 mi (14 km) from Mo...

Top Saint James Destination: Rose Hall Resort Packages from Chicago

Escape to the picturesque Rose Hall in Saint James with CheapCaribbean.com's 0 enticing package deals originating from Chicago that cater to every preference, whether it's for a package. Each deal is thoughtfully curated to include both your flight and accommodations at sought-after hotel brands, offering amenities such as spa, golf and exercise gym. Priced on a per-person basis, these packages span a range an average of per person, indicative of the value we deliver in Rose Hall.*

Holiday Inn Resort Montego Bay - All Inclusive Rose Hall
All-Inclusive
Dreaming of warm sun on your face and sand between your toes? Explore Holiday Inn Resort Montego Bay! This all-inclusive, beachfront property features beautiful, white sand beaches and great activitie...

FAQs about Chicago to Saint James Vacation Packages

What cities in Saint James have the highest rated hotels with packages offered that include a flight from Chicago - O'Hare?

In Saint James, the top-rated hotels that offer a flight from ORD are predominantly found in Montego Bay with 20 top rated hotels and Rose Hall with 1 top rated hotel.

What cities in Saint James have the cheapest packages available from Chicago?

For travelers from Chicago to Saint James, Montego Bay present the most budget-friendly vacation packages. Prices begin at $670 in Montego Bay.

What cities in Saint James offer family-friendly, luxury, or adults-only deals?

Montego Bay offers 12 family-friendly packages, 8 luxury packages and 8 adults-only packages.

What resort brands offer vacations from Chicago to Saint James?

Ocean by H10, Iberostar Hotels & Resorts, Blue Diamond Resorts - HBS, Riu Resorts and Hyatt Inclusive Collection currently have amazing package deals on flights from Chicago to Saint James with resort accommodations included. Here are some of their best deals as of 08-29-2024:

Explore More Vacations

*Current vacation package prices are listed as of 08-29-2024 and are subject to change based on dates, origins and availability.