Highland Hills
Chicago
Visit Highland Hills
Things to do
Skydeck Chicago at Willis Tower
CA $59
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $57
per adult
94% of travellers recommend
LEGOLAND® Discovery Center Chicago
CA $37
per adult
92% of travellers recommend
Museum of Illusions Chicago Admission Ticket
CA $60
per adult
Highland Hills Hotel Deals
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
The price is CA $138 per night from Oct 21 to Oct 22
CA $138
CA $153 total
Oct 21 - Oct 22
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! (3,055 reviews)
"Liked it so much I extended my stay by one more day, 40 min from down town Chicago, breakfast buffet was actually good, pankcakes , scrambled eggs, waffle, oatmeal, and other stuff,"
Reviewed on Oct 14, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
The price is CA $311 per night from Nov 13 to Nov 14
CA $311
CA $365 total
Nov 13 - Nov 14
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 ...
8.6/10 Excellent! (2,551 reviews)
"We were put in a room where our headboard was right up against the wall behind which was the elevator shaft! Noisiest room ever!"
Reviewed on Oct 13, 2026
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
The price is CA $216 per night from Nov 1 to Nov 2
CA $216
CA $274 total
Nov 1 - Nov 2
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! (1,247 reviews)
"good breakfast, friendly staff"
Reviewed on Oct 12, 2026
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
The price is CA $80 per night from Nov 12 to Nov 13
CA $80
CA $89 total
Nov 12 - Nov 13
includes taxes & fees
Book a stay at this business-friendly hotel in Westmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms ...
7.2/10 Good! (1,874 reviews)
"Very nice room with large hot tub in it."
Reviewed on Oct 14, 2026
Hyatt Place Chicago/Downtown - The Loop
28 North Franklin Street Chicago IL
The price is CA $277 per night from Nov 1 to Nov 2
CA $277
CA $330 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast ...
8.8/10 Excellent! (1,667 reviews)
"Our room was a corner city view, It was beautiful at night! Loved the room"
Reviewed on Oct 13, 2026
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $229 per night from Oct 30 to Oct 31
CA $229
CA $269 total
Oct 30 - Oct 31
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a free airport shuttle, and a 24-hour fitness center. Our guests praise ...
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 Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Photo by © City of Chicago
Open Photo by © City of Chicago
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.
