Highland Hills, IL
Chicago
Visit Highland Hills
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
90% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
LEGOLAND® Discovery Center Chicago
$29
per adult
92% of travellers recommend
Highland Hills Hotel Deals
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
$92 nightly
The price is $103 total per night from Aug 29 to Aug 30
$103 total
Aug 29 - Aug 30
Total with taxes and 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! (2,942 reviews)
"A/C did not dry out room air, the room was always very very humid"
Reviewed on Aug 7, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
$216 nightly
The price is $254 total per night from Aug 29 to Aug 30
$254 total
Aug 29 - Aug 30
Total with taxes and 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 ...
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
$169 nightly
The price is $193 total per night from Aug 30 to Aug 31
$193 total
Aug 30 - Aug 31
Total with taxes and 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 ...
8.8/10 Excellent! (2,966 reviews)
"We got a double bed room which was great and spacious but it doesn’t have a kitchen type amenities."
Reviewed on Aug 8, 2026
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
$154 nightly
The price is $183 total per night from Sep 8 to Sep 9
$183 total
Sep 8 - Sep 9
Total with taxes and 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 ...
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
$156 nightly
The price is $185 total per night from Aug 30 to Aug 31
$185 total
Aug 30 - Aug 31
Total with taxes and 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 ...
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2 Chicago IL
$220 nightly
The price is $261 total per night from Aug 9 to Aug 10
$261 total
Aug 9 - Aug 10
Total with taxes and 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! (2,493 reviews)
"Nice clean hotel Great staff! Easy walk to numerous restaurants and trains"
Reviewed on Aug 8, 2026
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. Learn more about Highland Hills
Learn more about Highland Hills
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 Lake Michigan are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
The Loop
Lake Michigan and Michigan Avenue 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.
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.
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.
Photo by Mattyboy876
Open Photo by Mattyboy876
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).
Highland Hills, IL
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- Visit Naperville
- Visit Hillside
- Visit Rush Street
- Visit Magnificent Mile
- Visit Oakbrook Terrace
- Visit Bedford Park
- Visit Addison
- Visit Villa Park
- Visit Berkeley
- Visit Glen Ellyn
- Visit Elk Grove Village
- Visit Franklin Park
- Visit Lisle
- Visit Melrose Park
- Chicago Vacations
- Where to stay in Chicago
- Visit Oak Brook
- Visit Downtown Chicago
- Visit The Loop
- Visit United Center
- Visit Oak Park
- Visit Chicago
- Visit Downers Grove
- Visit Elmhurst
- Visit Wheaton
- Visit Lombard
- Visit Schaumburg
- Visit Westmont
- Visit Hinsdale
- Visit Itasca
- Visit Clarendon Hills
- Visit Rosemont
