Highland Holidays
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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$177 per night from 3 Jun to 4 Jun
S$177
3 Jun - 4 Jun
includes taxes & fees
8.6/10 Excellent! (1,061 reviews)
"Always a nice stay."
Reviewed on 23 May, 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$218 per night from 26 May to 27 May
S$218
26 May - 27 May
includes taxes & fees
9.4/10 Exceptional! (391 reviews)
"The hotel staff was amazing and the bartenders and staff at the Alto Restaurant on the rooftop were also fantastic! The only complaints I have are that the AC did not cool down as well as we would have liked. The lowest we could get it to was 70/71 and it was not comfortable for sleeping. Also, the ..."
Reviewed on 25 May, 2026
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
The price is S$239 per night from 27 May to 28 May
S$239
27 May - 28 May
includes taxes & fees
6.8/10 (1,002 reviews)
"Nice staff, clean, nice spot. Definitely will stay here the next time I’m in Chicago"
Reviewed on 25 May, 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.
