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.

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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

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

Find hotel + flight trips 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$131 per night from 30 Nov to 1 Dec
AU$131
includes taxes & fees
30 Nov - 1 Dec
8.8/10 Excellent! (1,858 reviews)
"Nice one"

Reviewed on 25 Nov. 2024

SureStay Plus Hotel by Best Western Chicago Lombard
voco Chicago Downtown, an IHG Hotel
voco Chicago Downtown, an IHG Hotel
3.5 out of 5
350 W Wolf Point Plaza Building, Chicago, IL
Fully refundable
The price is AU$217 per night from 29 Dec to 30 Dec
AU$217
includes taxes & fees
29 Dec - 30 Dec
8.6/10 Excellent! (2,044 reviews)
"Nice place to stay"

Reviewed on 27 Nov. 2024

voco Chicago Downtown, an IHG Hotel
La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago Downtown
3 out of 5
1 S Franklin Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$160 per night from 22 Dec to 23 Dec
AU$160
includes taxes & fees
22 Dec - 23 Dec
8.6/10 Excellent! (2,167 reviews)
"It was clean, free breakfast, but parking is expensive"

Reviewed on 27 Nov. 2024

La Quinta Inn & Suites by Wyndham Chicago Downtown
See all 2,793 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 Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

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

McCormick Place

McCormick Place

4.5/5(21 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Navy Pier

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

Activities

Flyover in Chicago

Flyover in Chicago

AU$58
Per adult
94% of travellers recommend
Flyover in Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

AU$68
Per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
River tour boat in Chicago

Architecture River Tour

AU$75
Per adult
94% of travellers recommend
Architecture River Tour
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.