Highland Hills Holidays from AU$1,953

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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
Save 100% on your flight
Price was AU$2,926, price is now AU$1,953 per person
AU$1,953
per person
28 May - 1 June
found 7 hours ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
Great location and value

Reviewed on 25 Apr 2026

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Price was AU$4,759, price is now AU$3,797 per person
AU$3,797
per person
27 May - 1 June
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.6/10 Exceptional! (3,950 reviews)
Clean hotel great restaurant

Reviewed on 26 Apr 2026

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$2,538, price is now AU$2,118 per person
AU$2,118
per person
28 May - 1 June
found 7 hours ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
9/10 Wonderful! (1,519 reviews)
Have stayed on many occasions at the Claridge as it is a smaller hotel and located just where I like to be on the Gold Coast. Staff super friendly and helpful, have a nice happy hour. Only issue I had this trip is that our room was a terrible design, particularly that of the bathroom which seems to be stuck in where they could fit it. Difficult to navigate during the night, tight quarter and awkward door position. Other than that , had a great stay but would not stay again in that room

Reviewed on 21 Apr 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was AU$3,120, price is now AU$2,314 per person
AU$2,314
per person
29 May - 1 June
found 1 day ago
Return direct flight included
Honolulu (HNL) to Chicago (ORD)
9.2/10 Wonderful! (932 reviews)
We had a great time! Room was clean, spacious, and nice views! Staff was friendly and helpful. Will stay again

Reviewed on 26 Apr 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Price was AU$3,463, price is now AU$2,666 per person
AU$2,666
per person
29 May - 1 June
found 1 day ago
Return direct flight included
Honolulu (HNL) to Chicago (ORD)
9.2/10 Wonderful! (3,002 reviews)
Amazing location, great staff, room was luxurious, doormen were super friendly and helpful!

Reviewed on 24 Apr 2026

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

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$125 per night from 28 Apr to 29 Apr
AU$125
28 Apr - 29 Apr
includes taxes & fees
9/10 Wonderful! (2,703 reviews)
If you are traveling to Chicago I found this to be an excellent place. I stayed there two time and found it a very nice place, with free parking, and complimentary breakfast. Highly recommended if you are looking for a budget stay.

Reviewed on 26 Apr 2026

SureStay Plus Hotel by Best Western Chicago Lombard
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
Fully refundable
The price is AU$224 per night from 25 May to 26 May
AU$224
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (2,126 reviews)
.

Reviewed on 27 Apr 2026

Crowne Plaza Chicago West Loop by IHG
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$409 per night from 9 May to 10 May
AU$409
9 May - 10 May
includes taxes & fees
8.4/10 Very Good! (2,278 reviews)
State of the art gym, easy access to train

Reviewed on 27 Apr 2026

Hilton Chicago O'Hare Airport
See all 3,238 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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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$1,953. 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

Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
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

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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$38
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

AU$56
per adult
92% of travellers recommend
Art Institute of Chicago
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.