Highland Hills Vacations from $380

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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

Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
Hotel Riu Plaza Chicago
Palmer House a Hilton Hotel
Hilton Chicago
Hilton Chicago O'Hare Airport

Where to stay in Highland Hills

Find the best Highland Hills areas and neighborhoods for the activities you enjoy most. Learn more about Highland Hills

Highland Hills Hotel Deals

SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $80 total per night from Jan 13 to Jan 14
$80 total
Jan 13 - Jan 14
Total with taxes and fees
9/10 Wonderful! (2,478 reviews)
The Whole Hotel & its front desk, including our check-in & our Suite was A-1. Randy, Ernesto, Pat, Ken, Kim were Very Welcoming & Helpful. Breakfast & its staff & Housekeeping were Awesome.

Reviewed on Jan 7, 2026

SureStay Plus Hotel by Best Western Chicago Lombard
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
Fully refundable
$107 nightly
The price is $126 total per night from Jan 29 to Jan 30
$126 total
Jan 29 - Jan 30
Total with taxes and fees
8.8/10 Excellent! (2,104 reviews)
I love staying here. Great View. Staff is friendly.

Reviewed on Jan 10, 2026

Holiday Inn Chicago Dwtn - The Mart by IHG
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$196 nightly
The price is $230 total per night from Feb 6 to Feb 7
$230 total
Feb 6 - Feb 7
Total with taxes and fees
8.2/10 Very Good! (2,179 reviews)
We didn’t have breakfast included

Reviewed on Jan 11, 2026

Hilton Chicago O'Hare Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Highland Hills

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.