
Highland Hills Vacations from $352
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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 Riu Plaza Chicago
Reviewed on Oct 25, 2025


Pendry Chicago
Reviewed on Oct 16, 2025

theWit Chicago, a Hilton Hotel
Reviewed on Oct 20, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile
Reviewed on Oct 4, 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

SureStay Plus Hotel by Best Western Chicago Lombard
Clean Rooms
Reviewed on Oct 23, 2025

Crowne Plaza Chicago West Loop by IHG
The room was nice, clean, comfy bed. The front desk staff was super friendly and helpful, and the breakfast in the hotel was good.
Reviewed on Oct 23, 2025

Hyatt Regency O'Hare Chicago
Great location. Large rooms with large windows to let a lot of natural light in. My experience was super positive from when I checked in to when I left. I will most definitely be back
Reviewed on Oct 22, 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.

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.

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

Skydeck - Willis Tower Admission
























