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Your Highland Hills Vacation
Get ready to experience Highland Hills in your own style with a custom Highland Hills vacation package! Uncovering the best parts of this fascinating city is made easier with a base in a neighborhood such as Clarendon Hills, which is good for golfing, among plenty of other things. Yorktown Shopping Center and Lilacia Park are some of the major attractions to tour during a trip to Highland Hills. Expedia is here to help you escape your routine. Tailor your vacation to Highland Hills to suit your travel style, whatever that may be.
The Latest Highland Hills Vacation Packages

Hotel Felix River North/Magnificent Mile
Reviewed on Jul 9, 2025

Virgin Hotels Chicago
Reviewed on Jul 8, 2025

LondonHouse Chicago, Curio Collection by Hilton
Reviewed on Jul 11, 2025

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 Jul 7, 2025

Reviewed on Jul 11, 2025

Reviewed on Jul 10, 2025
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.

Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Things to do

Wendella's 90-min Chicago River Architecture Tour
