Highland Hills Vacations from $359

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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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
The Westin Michigan Avenue Chicago
Hotel Riu Plaza Chicago
The Emily Hotel
Trump International Hotel & Tower Chicago

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
$81 nightly
The price is $90 total per night from Oct 13 to Oct 14
$90 total
Oct 13 - Oct 14
Total with taxes and fees
8.8/10 Excellent! (2,286 reviews)
"Ver"

Reviewed on Oct 8, 2025

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
$159 nightly
The price is $187 total per night from Nov 2 to Nov 3
$187 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,929 reviews)
"Great hotel - great location. It's a bummer that the view from the restaurant/bar isn't as cool as it used to be, because of the new buildings in front of it, but it's still pretty - and the drinks and food are very good. Room was very nice and clean."

Reviewed on Oct 10, 2025

Holiday Inn Chicago Dwtn - The Mart by IHG
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
$144 nightly
The price is $164 total per night from Oct 26 to Oct 27
$164 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (2,048 reviews)
"a bit dated but great for catching an early morning fligjt"

Reviewed on Oct 9, 2025

Hyatt Regency O'Hare Chicago
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.