Your Highland Hills Vacation
Book a Highland Hills vacation package and discover the rhythm and vibe of this unique neighborhood. With all your travel plans taken care of, the only thing you need to worry about here is having a good time. Yorktown Shopping Center and Lilacia Park are two of the premier attractions nearby to stick on your itinerary during a trip to Highland Hills. No matter your travel goals or the size of your budget, booking your perfect Highland Hills vacation is easy with Expedia.
The Latest Highland Hills Vacation Packages
Aloft Chicago Downtown River North
Reviewed on May 29, 2024
Where to stay in Highland Hills
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Highland Hills Hotel Deals
Reviewed on May 29, 2024
Reviewed on May 30, 2024
Reviewed on May 31, 2024
Explore other types of vacation packages
Frequently asked questions
Discover the most popular places to visit in Highland Hills
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Six Flags Great America
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
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.
Things to do
Odyssey Lake Michigan Premier Dinner Cruise
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Chicago Pizza Tour
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals