Highland Hills Holidays from £944
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Your Highland Hills Holiday
Get ready to experience Highland Hills in your own style with a custom Highland Hills holiday package! Uncovering the best parts of this fascinating city is made easier with a base in a neighbourhood such as Clarendon Hills, which is good for golfing, among plenty of other things. Yorktown Shopping Centre and Lilacia Park are some of the major attractions to tour during a trip to Highland Hills. Expedia is here to help you escape your routine. Tailor your holiday to Highland Hills to suit your travel style, whatever that may be.
Where to stay in Highland Hills
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
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.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Highland Hills
SureStay Plus Hotel by Best Western Chicago Lombard
Hilton Chicago O'Hare Airport
"All of the staff that I encountered were very helpful and friendly. The thermostat in my room was broken so the maintenance staff put a large space heater in my room. Also, the room had a faint smell of cigarette smoke. The decor of the hotel is rather dated and could use a makeover. Overall, it ..."
Reviewed on 8 Oct 2026
Chicago Club Inn & Suites
Frequently asked questions
How much does a Highland Hills travel package cost?
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Does Expedia offer Book Now, Pay Later Highland Hills holidays?
- Pay monthly holidays: If paying bite-sized amounts each month sounds right for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams possible.
- Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your holiday over multiple transactions.
- Low deposit holidays: Clicking on the "book now" button is easier with this payment option. Simply put down a small deposit on your booking and then start working on your travel plans.
Where should I stay in Highland Hills?
What are the top hotels in Highland Hills?
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Things to do
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.