Highland Hills Travel Guide
Chicago
Visit Highland Hills
Popular places to visit
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
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.
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.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Things to do
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Top hotels in Highland Hills
SureStay Plus Hotel by Best Western Chicago Lombard
Breakfast was good.
Reviewed on 22 Apr 2026
Crowne Plaza Chicago West Loop by IHG
Great location, great staff, clean and spacious rooms. Only down side was no microwave in the room. We had delicious Chicago food we couldn’t eat later in the day. Overall great stay!
Reviewed on 21 Apr 2026
Hyatt Regency O'Hare Chicago
Charged 2 times, once through Expedia and then again through “Hyatt”. Watch charges closely if booking through Expedia. Hyatt itself is lovely!
Reviewed on 22 Apr 2026
Hilton Chicago O'Hare Airport
Convenient but very dated. Needs a renovation. And not cheap.
Reviewed on 21 Apr 2026
La Quinta Inn & Suites by Wyndham Chicago Downtown
Check-in was efficient and pleasant. The room was very clean. Breakfast was quite elaborate, unusual for a complimentary meal. One of the staff in the breakfast room was a ray of sunshine! Her name is Ariane and she deserves a raise. Her friendliness to every single patron was just lovely to behold. ...
Reviewed on 22 Apr 2026
Holiday Inn & Suites Chicago - Downtown by IHG
Safe cozy hotel Rooms
Reviewed on 21 Apr 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.
Logan Square
The breweries and live music are just a few things visitors like about Logan Square. Concord Music Hall and Milwaukee Avenue 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.
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.
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.
