Highland Hills Travel Guide

Tourist Guide

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$39
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$36
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

AU$58
per adult
92% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$59
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Spirit of Chicago Signature Lunch Cruise on Lake Michigan

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

AU$91
per adult
City Cruises Chicago: Signature Lunch Cruise on Lake Michigan
Color Factory Chicago Ticket

Color Factory Chicago Ticket

AU$49
per adult
96% of travellers recommend
Color Factory Chicago Ticket
See all activities in Chicago

Our pick of the best 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 AU$154 per night from 4 Aug to 5 Aug
AU$154
4 Aug - 5 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 ...
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 AU$325 per night from 6 Aug to 7 Aug
AU$325
6 Aug - 7 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 ...
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 AU$301 per night from 20 Aug to 21 Aug
AU$301
20 Aug - 21 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! (2,427 reviews)
"Good"

Reviewed on 26 July 2026

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 AU$345 per night from 20 Aug to 21 Aug
AU$345
20 Aug - 21 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! (2,475 reviews)
"Nice hotel in an area that was perfect for our stay! close to lots of food and drink options in a clean neighborhood."

Reviewed on 27 July 2026

Holiday Inn Chicago Dwtn - The Mart by IHG
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 AU$299 per night from 20 Aug to 21 Aug
AU$299
20 Aug - 21 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! (1,102 reviews)
"It has a great location in the west loop."

Reviewed on 27 July 2026

Holiday Inn & Suites Chicago - Downtown by IHG
DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr Naperville IL
The price is AU$137 per night from 16 Aug to 17 Aug
AU$137
16 Aug - 17 Aug
includes taxes & fees
Stay at this business-friendly hotel in Naperville. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
7.8/10 Good! (1,382 reviews)
"Great experience the whole weekend"

Reviewed on 27 July 2026

DoubleTree by Hilton Lisle Naperville
See all 3,139 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.

Our guide on where to stay in Highland Hills

Find the best Highland Hills areas 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 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

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