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.
Navy Pier
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
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.
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
Wendella's 90-min Chicago River Architecture Tour
Chicago By Night River & Lake Cruise
Chicago: Architecture Boat Tour with Drinks
Chicago: Navy Pier Centennial Wheel Ticket
Chicago River: 1.5-Hour Guided Architecture Riverboat Tour
Our pick of the best Highland Hills Hotel Deals
SureStay Plus Hotel by Best Western Chicago Lombard
Reviewed on 20 Jul. 2025
Crowne Plaza Chicago West Loop by IHG
Reviewed on 20 Jul. 2025
Holiday Inn Chicago Dwtn - The Mart by IHG
Reviewed on 20 Jul. 2025
Hilton Chicago O'Hare Airport
Reviewed on 23 Jul. 2025
Hyatt Regency O'Hare Chicago
Reviewed on 22 Jul. 2025
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Reviewed on 20 Jul. 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.
Logan Square
The breweries and live music are just a few things visitors like about Logan Square. Milwaukee Avenue and Logan Square Farmers Market are worthwhile spots to check out, and you can hop on the metro at Logan Square Station or California Station (Blue Line) to get around the larger 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.