
Highland Hills Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Holiday Package Deals in Highland Hills

La Banque Hotel
Reviewed on Jan 26, 2026

Hotel Riu Plaza Chicago
Reviewed on Feb 21, 2026

Level Chicago Fulton Market
Reviewed on Feb 16, 2026

JW Marriott Chicago
Reviewed on Feb 17, 2026
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. courteous
Reviewed on Feb 19, 2026

Hilton Chicago O'Hare Airport
We always enjoy staying here whenever we plan a trip where we fly out of O’Hare early. It is so convenient being connected directly to the Terminal.
Reviewed on Feb 20, 2026

Holiday Inn Chicago Dwtn - The Mart by IHG
Everything was great
Reviewed on Feb 19, 2026
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.

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














