
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
per person
8 May - 11 May
found 13 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Great location and beautiful hotel. However- room amenities were missing basic needs like iron, ironing boards, slippers, full length mirror and no working desk. Not good for business needs at all.
Reviewed on 1 Apr 2025

Hotel Riu Plaza Chicago
Downtown Chicago
per person
8 May - 11 May
found 13 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,605 reviews)
Enjoyed our stay!! Rooms were clean and breakfast was top tier with many options. They don’t have valet, but they do have self pay parking across the street for $55 a day. Front desk staff professional and helpful.
Reviewed on 1 Apr 2025

The Emily Hotel
Downtown Chicago
per person
8 May - 11 May
found 13 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,046 reviews)
What an amazing experience we had at The Emily. From their stylish coffee shop to their upscale dining experience, this is the place to stay if you are just visiting or looking for an escape from the 9 to 5. The local restaurants are absolute gems, and entertainment can be found in any direction. I’m booking my next stay now, can’t wait to be back in summer!
Reviewed on 30 Mar 2025
Top hotels in Highland Park

Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is €151 per night from 16 Apr to 17 Apr
€151
includes taxes & fees
16 Apr - 17 Apr
8.6/10 Excellent! (1,453 reviews)
"We missed our connecting flight at O’Hare, this hotel was close to the airport and an airport shuttle was available making it very convenient after a long day of travel with many delays. We didn’t have our checked bags and therefore didn’t have some necessities, it was late so we were unable to get ..."
Reviewed on 31 Mar 2025

Viceroy Chicago
1118 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €268 per night from 20 Apr to 21 Apr
€268
includes taxes & fees
20 Apr - 21 Apr
9.4/10 Exceptional! (1,004 reviews)
"This property was simply amazing. I recommend staying here. The staff were so accommodating. The views are breathtaking. My first time in Chicago was perfect because of my stay here. I will be back."
Reviewed on 28 Mar 2025

Thompson Chicago, by Hyatt
21 East Bellevue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €188 per night from 20 Apr to 21 Apr
€188
includes taxes & fees
20 Apr - 21 Apr
9/10 Wonderful! (1,036 reviews)
"Great location!"
Reviewed on 29 Mar 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.
Frequently asked questions
Popular places to visit

Wrigley Field
4.5/5(40 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
4.5/5(14 reviews)
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
4/5(125 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Highland Park

Chicago: Willis Tower Skydeck and The Ledge Ticket
€41
per adult
86% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.