Highland Hills Holidays from AU$2,121

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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.

Top Holiday Package Deals in Highland Hills

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$3,292, price is now AU$2,121 per person
AU$2,121
per person
25 Jan - 28 Jan
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
8.4/10 Very good! (3,148 reviews)
I stayed for a night before transferring to the main hotel while there for chicago marathon. Room was a little small but I was okay with given the price. Just know the standard rooms can be a little tight so don't be afraid to upgrade if you have lots of luggage.

Reviewed on 10 Nov 2026

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was AU$4,430, price is now AU$2,847 per person
AU$2,847
per person
25 Jan - 28 Jan
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was AU$3,634, price is now AU$2,346 per person
AU$2,346
per person
25 Jan - 28 Jan
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$4,057, price is now AU$2,628 per person
AU$2,628
per person
25 Jan - 28 Jan
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Amazing experience! Kurtis and Luis at concierge was great! I had a romantic arrangement in the room before arrival and they made it happen! Great great great 5 ✨

Reviewed on 9 Nov 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was AU$3,374, price is now AU$2,201 per person
AU$2,201
per person
25 Jan - 28 Jan
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (2,181 reviews)

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
A cityscape with tall skyscrapers and a historic tower.

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.

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$143 per night from 11 Nov to 12 Nov
AU$143
11 Nov - 12 Nov
includes taxes & fees
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$320 per night from 11 Dec to 12 Dec
AU$320
11 Dec - 12 Dec
includes taxes & fees
Hilton Chicago O'Hare Airport
Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop

3 out of 5
28 North Franklin Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 23 Nov to 24 Nov
AU$203
23 Nov - 24 Nov
includes taxes & fees
Hyatt Place Chicago/Downtown - The Loop
See all 3,224 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 AU$2,121. 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.

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$58
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

AU$61
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
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.