Highland Hills Travel Guide

Chicago

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

฿798
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago CityPASS: Admission to Top 5 Chicago Attractions

Chicago CityPASS®: Experience 5 must-see attractions

฿4,731
per adult
94% of travellers recommend
Chicago CityPASS®: Experience 5 must-see attractions
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

฿3,581
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
Art Institute of Chicago

Art Institute of Chicago

฿1,314
per adult
92% of travellers recommend
Art Institute of Chicago
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

฿5,074
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

฿795
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago

Top hotels in Highland Hills

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 ฿2,929 per night from 3 Aug to 4 Aug
฿2,929
฿3,251 total
3 Aug - 4 Aug
includes taxes & fees
Stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
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 11 Jul 2026

SureStay Plus Hotel by Best Western Chicago Lombard
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is ฿5,627 per night from 3 Aug to 4 Aug
฿5,627
฿6,413 total
3 Aug - 4 Aug
includes taxes & fees
Stay at this business-friendly hotel in Rosemont. Enjoy free Wi-Fi, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
8.8/10 Excellent! (2,814 reviews)
"Dated but comfortable and had all amenities"

Reviewed on 11 Jul 2026

Hyatt Regency O'Hare Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
The price is ฿9,289 per night from 2 Aug to 3 Aug
฿9,289
฿10,904 total
2 Aug - 3 Aug
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
8.4/10 Very good! (2,339 reviews)
"Very nice"

Reviewed on 11 Jul 2026

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 ฿5,761 per night from 9 Aug to 10 Aug
฿5,761
฿7,249 total
9 Aug - 10 Aug
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, an outdoor pool and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
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 11 Jul 2026

Holiday Inn & Suites Chicago - Downtown 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 ฿6,805 per night from 9 Aug to 10 Aug
฿6,805
฿9,080 total
9 Aug - 10 Aug
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 2 restaurants and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (2,442 reviews)
"Location is great, The HOTEL is located right on the Riverwalk Downtown Chicago."

Reviewed on 11 Jul 2026

Holiday Inn Chicago Dwtn - The Mart by IHG
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 ฿6,516 per night from 10 Aug to 11 Aug
฿6,516
฿7,748 total
10 Aug - 11 Aug
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the helpful staff in their reviews. ...
9/10 Wonderful! (2,361 reviews)
"We enjoyed our trip was very clean and helpful staff"

Reviewed on 10 Jul 2026

Crowne Plaza Chicago West Loop by IHG
See all 3,126 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 for the activities you enjoy most. Learn more about Highland Hills
Learn more about Highland Hills
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 Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

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 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 Travel Guide