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 Nov 11 to Nov 12
AED 281
AED 312 total
11 Nov - 12 Nov
includes taxes & fees
8.8/10 Excellent! (2,354 reviews)
I had a nice stay at the SureStay Plus Hotel in Lombard. The room was comfortable and clean, the breakfast had a good variety. When my room wasn’t cleaned one night, Patrick at the front desk was very helpful — he gave me fresh towels right away and confirmed that my room would be cleaned the next ...

Reviewed on 7 November 2025

SureStay Plus Hotel by Best Western Chicago Lombard
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is AED 331 per night from Nov 23 to Nov 24
AED 331
AED 388 total
23 Nov - 24 Nov
includes taxes & fees
8.8/10 Excellent! (1,656 reviews)
Great stay!

Reviewed on 6 November 2025

Crowne Plaza Chicago West Loop by IHG
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

3.5 out of 5
350 W Wolf Point Plaza Building, Chicago, IL
Fully refundable
The price is AED 382 per night from Nov 24 to Nov 25
AED 382
AED 448 total
24 Nov - 25 Nov
includes taxes & fees
8.6/10 Excellent! (3,334 reviews)
Room was good but it’s a bit weird that it’s both the Voco and a Holiday Inn and I can’t help but wonder if my room would have been the same room for less if I had reserved the Holiday Inn. Also entering the hotel is a bit weird - you check in in the building lobby and then must be directed to the ...

Reviewed on 8 November 2025

voco Chicago Downtown - Riverwalk by IHG
See all 3,190 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

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

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
McCormick Place showing a high rise building and a city

McCormick Place

During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.

McCormick Place