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.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Things to do
360 CHICAGO Observation Deck
Chicago CityPASS®: Experience 5 must-see attractions
Skydeck - Willis Tower Admission
Big Bus Chicago Hop-On Hop-Off Big Bus Tour
Top hotels in Highland Hills
SureStay Plus Hotel by Best Western Chicago Lombard
Fresh
Reviewed on 4 May 2026
Holiday Inn Chicago Dwtn - The Mart by IHG
The Holiday Inn Voco at Wolf Point continues to exceed expectations! Warm, welcoming staff, spotless rooms and outstanding service by housekeeping! I call it my home away from home and I stay there frequently when visiting our children! Spectacular views, inviting atmosphere and stay second to none! ...
Reviewed on 4 May 2026
Crowne Plaza Chicago West Loop by IHG
I travel to Chicago frequently, but I usually stay outside of the downtown area. I made an exception for this hotel as it was convenient to my event at the United Center. I was really impressed! The location was awesome, the entrance felt secluded, safe and not crowded yet walkable to dozens of restaurants, ...
Reviewed on 5 May 2026
Hyatt Regency O'Hare Chicago
Wonderful staff
Reviewed on 5 May 2026
Hilton Chicago O'Hare Airport
Wonderful location, staff were very helpful and room was clean. Older hotel but well maintained. Pricey but worthwhile for convenience sake.
Reviewed on 5 May 2026
Comfort Suites Chicago O'Hare Airport
The hotel was definitely old and outdated but was extremely clean. The staff was super friendly and the free shuttle to and from the airport was a nice perk. The shuttle drivers were friendly and helpful. The room was very clean and the beds were comfortable enough for a good sleep after a long international ...
Reviewed on 4 May 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.
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.
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.
