Highland Hills Travel Guide
Tourist Guide
Visit Highland Hills
Popular places to visit
Wrigley Field
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.
Michigan Avenue
You can find the perfect gifts to bring home 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
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
McCormick Place
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Millennium Park
See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Activities
Skydeck - Willis Tower Admission
Chicago Sightseeing River and Lake Cruise
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour
Chicago Architecture Center River Cruise aboard First Lady
Our pick of the best Highland Hills Hotel Deals
SureStay Plus Hotel by Best Western Chicago Lombard
This hotel is under renovation . Clean lobby , clean room . Excellent front desk workers . Very accommodating!
Reviewed on 24 Oct 2025
Holiday Inn Chicago Dwtn - The Mart by IHG
The room was very nice and clean. The bed was really comfortable. Staff was very helpful and the restaurant was excellent. Definitely would stay here again.
Reviewed on 20 Oct 2025
Crowne Plaza Chicago West Loop by IHG
The room was nice, clean, comfy bed. The front desk staff was super friendly and helpful, and the breakfast in the hotel was good.
Reviewed on 23 Oct 2025
voco Chicago Downtown - Riverwalk by IHG
The staff were quick to check us in and helpful with any questions we had. The views from our room were spectacular and the hotel is conveniently located. We dined at the hotel restaurant one night - the food and drinks were great and the staff there were so nice.
Reviewed on 24 Oct 2025
Hyatt Regency O'Hare Chicago
Great location. Large rooms with large windows to let a lot of natural light in. My experience was super positive from when I checked in to when I left. I will most definitely be back
Reviewed on 22 Oct 2025
Holiday Inn Chicago O'Hare – Rosemont by IHG
Very friendly staff clean facility
Reviewed on 24 Oct 2025
Other neighbourhoods around Highland Hills
O'Hare
Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Rosemont Station and check out top sights like Rosemont Theatre.
Wicker Park
Spend some time visiting places like Milwaukee Avenue while getting to know Wicker Park, and be sure to check out the abundant dining options. You can hop aboard the metro at Damen Station or Division Station to see more of the area.
West Town
Noted for its live music and theatres, there's plenty to explore in West Town. Top attractions like The Salt Shed and Milwaukee Avenue are major draws, and you can hop on the metro at Division Station or Damen Station to see more of the city.
Near West Side
Live music, theatres and shopping highlight some notable features of Near West Side. Make a stop by United Center or Credit Union 1 Arena while you're visiting, and jump aboard the metro at Racine Station or Polk Station (Pink Line) to get around town.
West Loop
Consider a visit to Milwaukee Avenue and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.
Lakeview
Known for its lively bars and lake views, there's plenty to explore in Lakeview. Top attractions like Wrigley Field and Lake Michigan are major draws, and you can catch the metro at Southport Station or Addison Station (Red Line) to see more of the city.
