Highland Hills Holidays

Book a Hotel + Flight or Car together to unlock savings

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

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

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

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

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

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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

Lincoln Park

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

Top hotels in Highland Hills

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

Fully refundableReserve now, pay when you stay

2.438.500 ₫

2.706.247 ₫ total

30 Aug - 31 Aug

includes taxes & fees

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

6.068.611 ₫

7.123.941 ₫ total

18 Sept - 19 Sept

includes taxes & fees

Holiday Inn & Suites Chicago - Downtown by IHG

506 West Harrison Street Chicago IL

Fully refundable

3.885.622 ₫

4.932.551 ₫ total

7 Sept - 8 Sept

includes taxes & fees

8.6/10 Excellent! (1,192 reviews)

"It was great"

Reviewed on 29 Aug 2026

See all 3,183 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 holiday package cost?

We make it easy to travel somewhere new, with Highland Hills holiday packages starting from as low as . You'll have the flexibility to combine your favourite 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 holiday 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 1null000null000 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 holiday!

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 Centre 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 holiday?

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 holiday package is the most convenient way to organise 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 holiday package?

Yes — and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our holiday 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 holiday package?

Don't worry if you're rethinking your Highland Hills holiday 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 realise 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.