Highland Hills Vacations

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Where to stay in Highland Hills

Find the best Highland Hills areas and neighborhoods for the activities you enjoy most. Learn more about Highland Hills
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Highland Hills Hotel Deals

SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
The price is AED 281 per night from Feb 11 to Feb 12
AED 281
AED 312 total
11 Feb - 12 Feb
includes taxes & fees
9/10 Wonderful! (2,545 reviews)
The only complaint I have is the carpet was not cleanedcleaned vacuumed

Reviewed on 4 February 2026

SureStay Plus Hotel by Best Western Chicago Lombard
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
Fully refundable
The price is AED 433 per night from Feb 19 to Feb 20
AED 433
AED 509 total
19 Feb - 20 Feb
includes taxes & fees
8.8/10 Excellent! (2,159 reviews)
The room was really clean and the hotel lobby/restaurant decorations were Lavish for the price. The view was the best thing! However, the pool wasn’t heated and wasn’t thought after. Variety in breakfast was really lacking. The lady at the front desk was really rude at check in, with concerns for ...

Reviewed on 4 February 2026

Holiday Inn Chicago Dwtn - The Mart by IHG
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is AED 720 per night from Mar 7 to Mar 8
AED 720
AED 845 total
7 Mar - 8 Mar
includes taxes & fees
8.2/10 Very Good! (2,218 reviews)
Food at sports bar was great along with the service. Bedding was top notch, room clean& nice TV

Reviewed on 9 February 2026

Hilton Chicago O'Hare Airport
See all 3,285 properties in Highland Hills
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.

Discover the most popular places to visit in Highland Hills

Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Navy Pier
Chicago Riverwalk which includes a city, a bay or harbor and a river or creek

Chicago Riverwalk

After visiting Chicago Riverwalk, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront in this vibrant area, or check out its top-notch restaurants.

Chicago Riverwalk