Highland Hills Vacations from $428

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, 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.

The Latest Highland Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Virgin Hotels Chicago
LondonHouse Chicago, Curio Collection by Hilton
Trump International Hotel & Tower Chicago
Hilton Garden Inn Chicago Downtown South Loop

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
$95 nightly
The price is $105 total per night from Jul 13 to Jul 14
$105 total
Jul 13 - Jul 14
Total includes taxes and fees
8.8/10 Excellent! (2,102 reviews)
"Staff are always nice and helpful. Rooms and property are clean and comfortable"

Reviewed on Jul 7, 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
$147 nightly
The price is $173 total per night from Aug 10 to Aug 11
$173 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (1,243 reviews)
"Room didn’t have a shower curtain and the night manager Jerry brought one right up and installed it. Also gave us complimentary breakfast buffets because of this"

Reviewed on Jul 11, 2025

Crowne Plaza Chicago West Loop 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
$179 nightly
The price is $210 total per night from Aug 8 to Aug 9
$210 total
Aug 8 - Aug 9
Total includes taxes and fees
8/10 Very Good! (2,064 reviews)
"Super convenient for an early morning flight, and surprisingly quiet considering it’s only steps from the terminal."

Reviewed on Jul 10, 2025

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.