Highland Hills
Chicago
Visit Highland Hills
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $35
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $58
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
CA $71
per adult
94% of travellers recommend
Highland Hills Hotel Deals
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Aug 3 to Aug 4
CA $125
CA $138 total
Aug 3 - Aug 4
includes taxes & fees
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (2,878 reviews)
"Everything was good, as this is our 3rd or 4th time at this hotel. But this was the first time we had a first floor accommodation. And the only problem we encountered were ants crawling on the table to get to our fountain pops."
Reviewed on Jul 11, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
The price is CA $239 per night from Aug 6 to Aug 7
CA $239
CA $273 total
Aug 6 - Aug 7
includes taxes & fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,814 reviews)
"Dated but comfortable and had all amenities"
Reviewed on Jul 11, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
The price is CA $359 per night from Aug 10 to Aug 11
CA $359
CA $421 total
Aug 10 - Aug 11
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very good! (2,339 reviews)
"Very nice"
Reviewed on Jul 11, 2026
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
The price is CA $245 per night from Aug 9 to Aug 10
CA $245
CA $308 total
Aug 9 - Aug 10
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,066 reviews)
"We had a nice time! Clean room and luv the rooftop pool. Only down fall breakfast prices."
Reviewed on Jul 11, 2026
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2 Chicago IL
The price is CA $289 per night from Jul 26 to Jul 27
CA $289
CA $386 total
Jul 26 - Jul 27
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (2,442 reviews)
"Location is great, The HOTEL is located right on the Riverwalk Downtown Chicago."
Reviewed on Jul 11, 2026
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
The price is CA $277 per night from Aug 10 to Aug 11
CA $277
CA $329 total
Aug 10 - Aug 11
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
9/10 Wonderful! (2,361 reviews)
"We enjoyed our trip was very clean and helpful staff"
Reviewed on Jul 10, 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.
Where to stay in Highland Hills
Find the best Highland Hills areas and neighborhoods for the activities you enjoy most.
Downtown Chicago
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.
Magnificent Mile
Michigan Avenue and Chicago Water Tower are just a few worthwhile attractions to visit in Magnificent Mile. Travelers also love the fascinating museums, panoramic lake views, and popular shops.
The Loop
Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops, and acclaimed art galleries.
River North
Known for its fantastic nightlife, stunning river views, and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.
