Highland Hills Travel Guide
Chicago
Visit Highland Hills
Popular places to visit
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.
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
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.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Things to do
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Ticket
Volo Auto Museum: Admission Ticket
Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting
Top hotels in Highland Hills
SureStay Plus Hotel by Best Western Chicago Lombard
Great breakfast. Friendly people
Reviewed on 3 Jan 2026
Holiday Inn Chicago Dwtn - The Mart by IHG
Room was amazing, bed was comfy, staff were so nice. Definitely going to be our go to hotel for when we go to Chicago
Reviewed on 5 Jan 2026
Hilton Chicago O'Hare Airport
Checkin staff were very nice and professsional.
Reviewed on 2 Jan 2026
Crowne Plaza Chicago West Loop by IHG
Modern property
Reviewed on 5 Jan 2026
Hyatt Regency O'Hare Chicago
Very clean room and very nice staff can’t wait to go back
Reviewed on 1 Jan 2026
voco Chicago Downtown - Riverwalk by IHG
The room was really nice and the workers were so awesome!!!
Reviewed on 6 Jan 2026
Other neighbourhoods around Highland Hills
O'Hare
Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago.
Lawndale
When in Lawndale and the surrounding area, you'll want to check out sights like United Center or Garfield Park Conservatory and hop on the metro to see more of the city at Central Park Station (Pink Line) or Pulaski Station (Pink Line).
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 Polk Station (Pink Line) or Racine Station 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.
