Highland Holidays
Photo by Joe Farmer
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Top Flight + Hotel Deals in Highland
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,671, price is now €1,091 per person
€1,091
per person
1 Feb - 6 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Absolutely loved the hotel.Grand Dulxe Suite was huge with amazing views.All staff top notch.
Reviewed on 27 Dec 2025
Pendry Chicago
Downtown Chicago
Price was €1,282, price is now €913 per person
€913
per person
14 Mar - 20 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
A very clean room, everything smells good and fresh, very nice staff, the staff helps all the time, my family and I feels very secure in the hotel.
Reviewed on 27 Dec 2025
The Peninsula Chicago
Downtown Chicago
Price was €1,746, price is now €1,272 per person
€1,272
per person
1 Feb - 6 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Beautifully decorated for Christmas. Spotless as always.
Reviewed on 27 Dec 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was €866, price is now €636 per person
€636
per person
1 Feb - 6 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on 18 Dec 2025
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 €94 per night from 4 Jan to 5 Jan
€94
4 Jan - 5 Jan 2026
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
Ok
Reviewed on 22 Dec 2025
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €72 per night from 11 Jan to 12 Jan
€72
11 Jan - 12 Jan 2026
includes taxes & fees
6.8/10 (208 reviews)
The handle for the sink wasn’t put on properly making it difficult to turn the water on. Otherwise everything was great.
Reviewed on 17 Dec 2025
Hilton Chicago/Oak Lawn
9333 S Cicero Ave Oak Lawn IL
Fully refundableReserve now, pay when you stay
The price is €123 per night from 4 Jan to 5 Jan
€123
4 Jan - 5 Jan 2026
includes taxes & fees
8.2/10 Very Good! (1,152 reviews)
The room was clean. Bathroom could use some attention in the toilet area
Reviewed on 22 Dec 2025
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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