Highland Hills Vacations from $263

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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.
Bridgeview Inn Chicago Area

Bridgeview Inn Chicago Area

2 out of 5
Save 100% on your flight
Price was $430, price is now $263 per person
$263
per person
Mar 16 - Mar 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
6.4/10 (105 reviews)
Newly remodeled room.

Reviewed on Oct 11, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $628, price is now $354 per person
$354
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
The room was spotless and the staff was good. Loved the hotel. Was just an overnight stay. Wish we had stayed another day. Loved the area.

Reviewed on Nov 30, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,021, price is now $582 per person
$582
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on Dec 18, 2025

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,689, price is now $1,069 per person
$1,069
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.

Reviewed on Jan 5, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $806, price is now $512 per person
$512
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean room, great breakfast, close to Trader Joe's!!

Reviewed on Jan 9, 2026

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
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

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
$75 nightly
The price is $83 total per night from Jan 15 to Jan 16
$83 total
Jan 15 - Jan 16
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
$103 nightly
The price is $121 total per night from Jan 22 to Jan 23
$121 total
Jan 22 - Jan 23
Total with taxes and fees
8.8/10 Excellent! (2,092 reviews)
Loved the staff, all of them were friendly. The restaurant team was personally our best.

Reviewed on Jan 6, 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! (2,199 reviews)
Our check in between flights was so friendly , efficient and competent . Ella is great . This easiest to access the property form terminal 2 .

Reviewed on Jan 5, 2026

Hilton Chicago O'Hare Airport
See all 3,279 properties in Highland Hills
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Highland Hills

Magnificent Mile - River North showing night scenes, a city and signage

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.

Michigan Avenue
Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$83
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.