
Highland Hills Vacations from $359
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Find the right fit
Rest easy
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

Sable at Navy Pier Chicago, Curio Collection by Hilton
Reviewed on Oct 11, 2025

The Westin Michigan Avenue Chicago
Reviewed on Oct 2, 2025

Hotel Riu Plaza Chicago
Reviewed on Oct 10, 2025

The Emily Hotel
Reviewed on Oct 10, 2025

Trump International Hotel & Tower Chicago
Reviewed on Oct 6, 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
Reviewed on Oct 8, 2025

Holiday Inn Chicago Dwtn - The Mart by IHG
Reviewed on Oct 10, 2025

Hyatt Regency O'Hare Chicago
Reviewed on Oct 9, 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
