Highland Hills, IL

Chicago

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,920
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

￥7,518
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,384
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago's Navy Pier Centennial Wheel Ticket

Chicago's Navy Pier Centennial Wheel Ticket

￥3,863
per adult
100% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
Flyover in Chicago

Flyover in Chicago

￥4,997
per adult
96% of travellers recommend
Flyover in Chicago
See all activities in 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
The price is ￥14,899 per night from Aug 30 to Aug 31
￥14,899
￥16,535 total
Aug 30 - Aug 31
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 ...
SureStay Plus Hotel by Best Western Chicago Lombard
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
The price is ￥36,901 per night from Sep 18 to Sep 19
￥36,901
￥43,318 total
Sep 18 - Sep 19
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 ...
Hilton Chicago O'Hare Airport
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
The price is ￥23,745 per night from Sep 7 to Sep 8
￥23,745
￥30,140 total
Sep 7 - Sep 8
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 ...
Holiday Inn & Suites Chicago - Downtown by IHG
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is ￥28,525 per night from Sep 7 to Sep 8
￥28,525
￥32,512 total
Sep 7 - Sep 8
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 ...
9/10 Wonderful! (3,067 reviews)
"Very courteous and friendly staff. Clean rooms and facility. Very efficient airport shuttles."

Reviewed on Aug 28, 2026

Hyatt Regency O'Hare Chicago
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
The price is ￥28,310 per night from Aug 30 to Aug 31
￥28,310
￥33,659 total
Aug 30 - Aug 31
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 ...
Crowne Plaza Chicago West Loop by IHG
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
The price is ￥28,310 per night from Aug 30 to Aug 31
￥28,310
￥38,394 total
Aug 30 - Aug 31
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! (2,517 reviews)
"This was one of my favorite stays in Chicago. The rooms are clean, they have a coffee shop and full bar available and the staff was super helpful and friendly. The pool was okay. I would’ve wished for it to be outdoors but my little one loved it no matter what. Breakfast, great. Couldn’t have asked ..."

Reviewed on Aug 27, 2026

Holiday Inn Chicago Dwtn - The Mart by IHG
See all 3,165 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.

Where to stay in Highland Hills

Find the best Highland Hills areas and neighborhoods for the activities you enjoy most.
A busy city street with tall buildings, a bus, and cars.

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.

A river with yellow boats, a bridge, and tall buildings.

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.

A historic castle-like building with intricate stonework and a paved walkway.

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.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

A river with a city skyline in the background, surrounded by green trees and grass.

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.

Highland Hills, IL