Highland Hills Vacations from $442

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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 Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$442

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (2,960 reviews)

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$1,424

per person

Oct 5 - Oct 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (556 reviews)

Great! But parking was bad.

Reviewed on Aug 26, 2026

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$900

per person

Oct 15 - Oct 18

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,553 reviews)

Everything was amazing, but I only stayed for one night so we haven’t really checked out what the hotel has to offer. My only surprise was an urban fee that I had to pay when checking out. I didn’t know what it was for, I will have to call to see what it is. Otherwise it was a great experience, thanks.

Reviewed on Aug 29, 2026

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Save 100% on your flight

$476

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.4/10 Very Good! (2,146 reviews)

Great stay!

Reviewed on Aug 29, 2026

Kinzie Hotel

Downtown Chicago

Save 100% on your flight

$497

per person

Nov 18 - Nov 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (2,218 reviews)

Excellent location, friendly and considerate staff, room was spacious and bathrooms were clean. Super nice gym, happy hours from 5 pm - 7 pm with beer/wine and bar snacks. Breakfast was decent. Overall great location and stay for the price.

Reviewed on Aug 28, 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

A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Highland Hills Hotel Deals

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

Fully refundableReserve now, pay when you stay

$93 nightly

$104 total

Aug 30 - Aug 31

Total with taxes and fees

9/10 Wonderful! (2,981 reviews)

"Staff is amazing, breakfast was delicious, and room was immaculate! Great area to dine on anything your ❤️ desires!!!"

Reviewed on Aug 29, 2026

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

$253 nightly

$297 total

Sep 19 - Sep 20

Total with taxes and fees

8.4/10 Very Good! (2,457 reviews)

"Checking in and out was a breeze"

Reviewed on Aug 29, 2026

Holiday Inn & Suites Chicago - Downtown by IHG

506 West Harrison Street Chicago IL

Fully refundable

$159 nightly

$189 total

Sep 7 - Sep 8

Total with taxes and fees

See all 3,165 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.