Highland Hills Vacation Packages

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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.

Top Holiday Package Deals in Highland Hills

Price found within the past 48 hours. Click for updated prices.

The Talbott, Autograph Collection

Downtown Chicago

CA $941

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (179 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,128

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (5,404 reviews)

Great food, very helpful staff

Reviewed on Oct 10, 2026

The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

CA $944

per person

Dec 12 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

8/10 Very good! (2,382 reviews)

We loved the location. The hotel lobby and bar was nice. The breakfast buffet was an average buffet, nothing fancy. Our room was on the small side and the furniture needs some upgrading. The room was clean and we would stay there again. Friendly staff. The person whom booked on Expedia in front of me had there room denied, due to overbooking. They did not offer them a room at another hotel. The staff told the person to contact Expedia. You may want to call the hotel a couple of days before to make sure your booking is accepted. My booking was luckily accepted. Tip for dog owners: if your dog is only urinates on grass, there are patches of grass a couple of blocks east on Lake Shore Drive.

Reviewed on Oct 10, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

CA $1,770

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (2,035 reviews)

Park Hyatt Chicago

Downtown Chicago

CA $1,460

per person

Dec 11 - Dec 13

found 16 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Chicago (ORD)

9.6/10 Exceptional! (1,003 reviews)

Excellent experience. I’d recommend this property for their outstanding service and updated rooms.

Reviewed on Oct 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

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 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 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 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

CA $138

CA $153 total

Oct 28 - Oct 29

includes taxes & fees

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

CA $302

CA $354 total

Oct 31 - Nov 1

includes taxes & fees

Chicago Club Inn & Suites

630 Pasquinelli Dr Westmont IL

Fully refundableReserve now, pay when you stay

CA $80

CA $89 total

Nov 9 - Nov 10

includes taxes & fees

See all 3,211 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.

Frequently asked questions

How much does a Highland Hills vacation package cost?

We make it easy to travel somewhere new, with Highland Hills vacation packages starting from as low as CA $941. You'll have the flexibility to combine your favorite airlines, hotels and car rental. For the ultimate escape, why not add a couple of tours and experiences to your travel itinerary?

How do I get a cheap travel package to Highland Hills?

If you love landing a bargain, bundle your bookings into a Highland Hills vacation package. Whether you're chasing hotels, flights, rental cars or day tours, you can book them all in one place. You'll have plenty of choice at your fingertips too. Expedia has over 550 airlines and 1,000,000 hotel options worldwide to choose from. Fly with who you prefer, stay wherever you like and save a pretty penny — now that's the perfect vacation!

Where should I stay in Highland Hills?

There's so much to see in Highland Hills, so spend your nights close to its top attractions and treat yourself to more time sightseeing. Yorktown Shopping Center is one spot to put on your must-see list.

What are the top hotels in Highland Hills?

Sonesta ES Suites Chicago - Lombard and SureStay Plus Hotel by Best Western Chicago Lombard are a couple of the most sought-after properties in Highland Hills. Why not have a look at the facilities and rates at each and then decide?

How far in advance should I book my Highland Hills vacation?

While not all air carriers release ticket prices early, you can usually look up international fares on Expedia up to 12 months in advance. This is when you'll score some incredible bargains. If you're purchasing tickets last minute, there's a chance you could get lucky. Sometimes the cheapest prices emerge only weeks before departure.

What does an Expedia Highland Hills travel package include?

Expedia has all you need to arrange your Highland Hills trip, but what your package looks like is your choice. Select from any combination of flights, hotels and rental cars. In search of some experiences or tours to keep you busy? Once you've made your booking, you can add them on too. No matter your style or budget, there's a deal to suit your needs.

What should I know before booking a Highland Hills travel package?

Bundling your bookings into a Highland Hills vacation package is the most convenient way to organize your trip. Not only that, you'll save just for combining your flights, hotels and car rentals. Once you've booked, why not add on a tour or an activity?

Can I choose my airline with a Highland Hills Expedia vacation package?

Yes — and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our vacation packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.

If I'm not able to travel, can I cancel my Highland Hills vacation package?

Don't worry if you're rethinking your Highland Hills vacation package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We realize life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.

Things to do

360 CHICAGO Observation Deck

CA $34

per adult

86% of travellers recommend

Skydeck Chicago at Willis Tower

CA $59

per adult

88% of travellers recommend

Wendella's Lake and River Architecture Tour

CA $63

per adult

94% of travellers recommend

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.

Highland Hills Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Highland Hills Vacation

Top Holiday Package Deals in Highland Hills

The Talbott, Autograph Collection

Hotel Riu Plaza Chicago

The Chicago Hotel Collection Ambassador Gold Coast

Trump International Hotel & Tower Chicago

Park Hyatt Chicago

Where to stay in Highland Hills

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Highland Hills Hotel Deals

SureStay Plus Hotel by Best Western Chicago Lombard

Hilton Chicago O'Hare Airport

Chicago Club Inn & Suites

Frequently asked questions

Things to do

360 CHICAGO Observation Deck

Skydeck Chicago at Willis Tower

Wendella's Lake and River Architecture Tour