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.
Pendry Chicago
Downtown Chicago
Price was €1,061, price is now €937 per person
€937
per person
28 Apr - 30 Apr
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on 31 Jan 2026
Top hotels in Highland Park
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is €195 per night from 14 Mar to 15 Mar
€195
14 Mar - 15 Mar
includes taxes & fees
8.4/10 Very Good! (2,219 reviews)
clean, convenient, friendly staff
Reviewed on 19 Feb 2026
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
The price is €111 per night from 22 Mar to 23 Mar
€111
22 Mar - 23 Mar
includes taxes & fees
8.6/10 Excellent! (2,745 reviews)
Clean
Reviewed on 18 Feb 2026
Comfort Suites Chicago O'Hare Airport
4200 North River Road Schiller Park IL
Fully refundableReserve now, pay when you stay
The price is €59 per night from 23 Feb to 24 Feb
€59
23 Feb - 24 Feb
includes taxes & fees
8/10 Very Good! (2,901 reviews)
Nice and quiet!
Reviewed on 19 Feb 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.
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
Chicago: Navy Pier Centennial Wheel Ticket
€20
per adult
88% of travellers recommend
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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.
