Highland Hills Vacations
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Where to stay in 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 Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Highland Hills Hotel Deals
SureStay Plus Hotel by Best Western Chicago Lombard
I had a nice stay at the SureStay Plus Hotel in Lombard. The room was comfortable and clean, the breakfast had a good variety. When my room wasn’t cleaned one night, Patrick at the front desk was very helpful — he gave me fresh towels right away and confirmed that my room would be cleaned the next ...
Reviewed on 7 November 2025
Crowne Plaza Chicago West Loop by IHG
Great stay!
Reviewed on 6 November 2025
voco Chicago Downtown - Riverwalk by IHG
Room was good but it’s a bit weird that it’s both the Voco and a Holiday Inn and I can’t help but wonder if my room would have been the same room for less if I had reserved the Holiday Inn. Also entering the hotel is a bit weird - you check in in the building lobby and then must be directed to the ...
Reviewed on 8 November 2025
Discover the most popular places to visit in Highland Hills
Wrigley Field
Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its fascinating museums.