Highland Holidays
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Highland Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Grand Royal Hotel O'Hare - Chicago
Price was S$907, price is now S$691 per person
S$691
per person
28 Mar - 4 Apr
found 1 day ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
5.8/10 (215 reviews)
Friendly front desk, easy and convenient for my overnight layover in Chicago
Reviewed on 7 Nov, 2025
Hilton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
Price was S$2,021, price is now S$1,404 per person
S$1,404
per person
28 Mar - 4 Apr
found 1 day ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Great stay fir early flights
Reviewed on 8 Jan, 2026
Hilton Rosemont Chicago O'Hare
Price was S$1,516, price is now S$1,165 per person
S$1,165
per person
28 Mar - 4 Apr
found 1 day ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
The room and staff were extremely friendly, but I specifically requested a room with a bath so I could soak my leg after a surgery. There was absolutely no water pressure when it came to the bath and the drain wouldn't close all the way. For how much I paid I feel like I should have been able to take a bath
Reviewed on 8 Dec, 2025
DoubleTree by Hilton Chicago - Oak Brook
Price was S$1,245, price is now S$957 per person
S$957
per person
28 Mar - 4 Apr
found 1 day ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
6.8/10 (1,000 reviews)
Hotel is old and showing its age.
Rooms are old too. Few amenities etc.
Reviewed on 6 Jan, 2026
Top hotels in Highland
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
The price is S$142 per night from 19 Jan to 20 Jan
S$142
19 Jan - 20 Jan
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
Clean room
Reviewed on 7 Jan, 2026
Hilton Chicago/Oak Lawn
9333 S Cicero Ave Oak Lawn IL
Fully refundableReserve now, pay when you stay
The price is S$169 per night from 18 Jan to 19 Jan
S$169
18 Jan - 19 Jan
includes taxes & fees
8.2/10 Very Good! (1,170 reviews)
Rooms are always clean, the staff is always welcoming and nice to you and it’s located near everything.
Reviewed on 6 Jan, 2026
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
The price is S$215 per night from 12 Jan to 13 Jan
S$215
12 Jan - 13 Jan
includes taxes & fees
9.2/10 Wonderful! (225 reviews)
Everything
Reviewed on 10 Jan, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
