Highland Hills Holidays

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Your Highland Hills Holiday

Book a Highland Hills holiday package and experience the rhythm and lifestyle of this fascinating neighbourhood. With all your travel plans taken care of, the only thing you need to worry about here is having a great time. Of course, you'll want to do some sightseeing during your trip to Highland Hills. Make sure you check out nearby attractions such as Yorktown Shopping Centre and Lilacia Park. Stop daydreaming and start doing. When it's time to lock in your dream holiday to Highland Hills, Expedia will help get you there.

Our guide on 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 featuring 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

Our pick of the best 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
The price is AU$112 per night from 12 Mar to 13 Mar
AU$112
12 Mar - 13 Mar
includes taxes & fees
9/10 Wonderful! (2,605 reviews)
Great staff, comfortable room except for the hanging system in the wardrobe. 2 hangers were broken and the system is hard to reach to try to put the hanger into a little hole to hang clothesPrefer a regular hanging rod as I always bring my own hangers. . Internet/WiFi was very hit & miss. But everything ...

Reviewed on 10 Mar 2026

SureStay Plus Hotel by Best Western Chicago Lombard
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
The price is AU$323 per night from 3 Apr to 4 Apr
AU$323
3 Apr - 4 Apr
includes taxes & fees
8.4/10 Very Good! (2,234 reviews)
We only stayed because we had to make a connection in the morning and it is the hotel attached to the airport

Reviewed on 10 Mar 2026

Hilton Chicago O'Hare Airport
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$209 per night from 3 Apr to 4 Apr
AU$209
3 Apr - 4 Apr
includes taxes & fees
8.6/10 Excellent! (1,231 reviews)
Very nice property. Blue line from airport to downtown stops right in parking lot

Reviewed on 10 Mar 2026

Marriott Chicago O'Hare
See all 3,233 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.
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Beach Holidays
Beach Holidays

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 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 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.

Discover the most popular places to visit in Highland Hills

Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(64 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Chicago_UnitedCenter_6064077_01

United Center

5/5(8 reviews)

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

United Center

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$57
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$62
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
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.