Highland Holidays
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Top Flight + Hotel Deals in Highland
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was €3,053, price is now €1,918 per person
€1,918
per person
1 Aug - 6 Aug
found 10 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (488 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on 22 May 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €2,225, price is now €1,570 per person
€1,570
per person
1 Aug - 6 Aug
found 10 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
Without a doubt, the view of the pier and city skyline was the BEST part of this hotel experience. The room was pretty large and had a great sitting area to read, gaze at the water, people watch, and relax. The hotel staff was nice and helpful. Everything I needed and wanted to do for this trip was at the Navy Pier so the Sable Hotel checked all my boxes.
Reviewed on 28 May 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was €2,604, price is now €1,857 per person
€1,857
per person
1 Aug - 6 Aug
found 10 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
What a great place to stay!! So clean and so convenient. Thank you!!! I will return soon
Reviewed on 30 May 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €2,272, price is now €1,641 per person
€1,641
per person
1 Aug - 6 Aug
found 10 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
I enjoyed our stay at LondonHouse Chicago, Curio Collection by Hilton. Staff members were friendly and helpful! Housekeeping staff were friendly and on point with cleaning! My next visit to Chicago, I plan on staying there.
Reviewed on 27 May 2026
Top hotels in Highland
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
The price is €160 per night from 10 Jun to 11 Jun
€160
10 Jun - 11 Jun
includes taxes & fees
6.8/10 (1,001 reviews)
"Nice staff, clean, nice spot. Definitely will stay here the next time I ’m in Chicago"
Reviewed on 25 May 2026
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
The price is €123 per night from 14 Jun to 15 Jun
€123
14 Jun - 15 Jun
includes taxes & fees
8.4/10 Very Good! (1,063 reviews)
"Pool was closed “for repairs.”"
Reviewed on 29 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 €154 per night from 4 Jun to 5 Jun
€154
4 Jun - 5 Jun
includes taxes & fees
9.4/10 Exceptional! (401 reviews)
"Great room Great hotel ...When you get a chance treat yourself and others and book a room"
Reviewed on 29 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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