Highland Hills Travel Guide

Chicago

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

฿893
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

฿1,559
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Art Institute of Chicago

Art Institute of Chicago

฿1,324
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago CityPASS: Admission to Top 5 Chicago Attractions

Chicago CityPASS®: Experience 5 must-see attractions

฿4,765
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®

฿3,607
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

฿813
per adult
90% 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 ฿3,164 per night from 2 Sept to 3 Sept
฿3,164
฿3,511 total
2 Sept - 3 Sept
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 ...
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
Fully refundableReserve now, pay when you stay
The price is ฿7,991 per night from 18 Sept to 19 Sept
฿7,991
฿9,381 total
18 Sept - 19 Sept
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 ...
Hilton Chicago O'Hare Airport
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 ฿5,645 per night from 30 Aug to 31 Aug
฿5,645
฿6,712 total
30 Aug - 31 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! (2,554 reviews)
"Loved our stay"

Reviewed on 26 Aug 2026

Crowne Plaza Chicago West Loop 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 ฿5,851 per night from 7 Sept to 8 Sept
฿5,851
฿6,669 total
7 Sept - 8 Sept
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 ...
Hyatt Regency O'Hare Chicago
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 ฿4,871 per night from 7 Sept to 8 Sept
฿4,871
฿6,183 total
7 Sept - 8 Sept
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! (1,184 reviews)
"Everything was great!"

Reviewed on 25 Aug 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 ฿6,314 per night from 31 Aug to 1 Sept
฿6,314
฿8,479 total
31 Aug - 1 Sept
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 ...
Holiday Inn Chicago Dwtn - The Mart by IHG
See all 3,183 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 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

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 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