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

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Art Villa
Pendry Chicago
theWit Chicago, a Hilton Hotel
Hilton Grand Vacations Club Chicago Magnificent Mile

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 27 to Oct 28
$90 total
Oct 27 - Oct 28
Total with taxes and fees
8.8/10 Excellent! (2,313 reviews)
Clean Rooms

Reviewed on Oct 23, 2025

SureStay Plus Hotel by Best Western Chicago Lombard
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
$102 nightly
The price is $120 total per night from Nov 26 to Nov 27
$120 total
Nov 26 - Nov 27
Total with taxes and fees
8.8/10 Excellent! (1,617 reviews)
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

Crowne Plaza Chicago West Loop by IHG
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $134 total per night from Nov 24 to Nov 25
$134 total
Nov 24 - Nov 25
Total with taxes and fees
8.6/10 Excellent! (2,093 reviews)
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

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.