
Highland Park Holidays
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Top Flight + Hotel Deals in Highland Park
Price found within the past 48 hours. Click for updated prices.

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €819, price is now €673 per person
€673
per person
18 Dec - 22 Dec
found 24 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,188 reviews)
It was a beautiful room with an absolutely gorgeous view. The staff was friendly and helpful.
Reviewed on 5 Nov 2025

Park Hyatt Chicago
Downtown Chicago
Price was €1,776, price is now €1,391 per person
€1,391
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on 20 Oct 2025

Level Chicago – Old Town
Downtown Chicago
Price was €1,354, price is now €1,077 per person
€1,077
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
This was our first time at Level Chicago -Old Town. Last year we stayed at Level Chicago - North. Both apartments were really cozy and offered amazing views of the city. Old Town is a great place to stay, the staff overall was professional and polite. The unit was mostly clean, however, some of the towel were stained (seemed like he make up did not come off with bleach). It wasn't to my liking so I did not use them. Also, they knew we were six people but only gave 4 bath towels. I had to request additional. Another thing is that the locks in the bathroom and bedrooms were not working. It was a bit frustrating considering 6 people were sharing one bathroom.
The apartment itself is very comfortable, has washer and dryer on site, which is convenient, especially when staying with children. The kitchen was equipped with all the basic needs except a good coffee machine. They have a nespresso machine but I would have rather an actual coffee machine not espresso machine.
Safety was key. My family and I felt safe in the building and the area. Parking was not available in the building (the cost is $70 per night) but that wasnt an issue because we found plenty of parking right outside by the meters.
Reviewed on 29 Oct 2025

Top hotels in Highland Park

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd, Wood Dale, IL
Fully refundableReserve now, pay when you stay
The price is €86 per night from 27 Nov to 28 Nov
€86
27 Nov - 28 Nov
includes taxes & fees
8/10 Very Good! (1,001 reviews)
Good
Reviewed on 6 Nov 2025

Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €182 per night from 28 Nov to 29 Nov
€182
28 Nov - 29 Nov
includes taxes & fees
8.2/10 Very Good! (2,193 reviews)
PROs: comfortable bed, clean bathroom, heater is working, different TV show choices to watch, toiletries ( other than toothbrush and toothpaste ) are provided, room card/key needed to use the elevator, great accessibility when flying via Ohare airport and wanting to stay ( used the tram ), there ...
Reviewed on 4 Nov 2025

Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
The price is €116 per night from 30 Nov to 1 Dec
€116
30 Nov - 1 Dec
includes taxes & fees
8.6/10 Excellent! (2,118 reviews)
The room was clean, great service at the hotel bar, ambiance of the hotel was welcoming.
Reviewed on 31 Oct 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.
Popular places to visit

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Highland Park

Skydeck - Willis Tower Admission
€38
per adult
98% of travellers recommend

Chicago Sightseeing River and Lake Cruise
€38
per adult
98% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


