Highland Hills Holidays from AU$807

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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.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Sept - 3 Oct
found 7 hours ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
Had a great stay. Staff was friendly and helpful. Room was clean.

Reviewed on 19 Jul. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Sept - 3 Oct
found 7 hours ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Just a great property- really a 5 star experience-great location

Reviewed on 20 Jul. 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Sept - 3 Oct
found 7 hours ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on 13 Jun. 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Sept - 3 Oct
found 7 hours ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
The property in itself was not terrible, but I expected better.

Reviewed on 19 Jul. 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Sept - 3 Oct
found 7 hours ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
Beautiful property, will definitely stay there again.

Reviewed on 19 Jul. 2025

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$174 per night from 21 July to 22 July
AU$174
21 July - 22 July
includes taxes & fees
8.8/10 Excellent! (2,124 reviews)
Awesome hotel
"Clean and polite staff"

Reviewed on 17 Jul. 2025

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$296 per night from 10 Aug to 11 Aug
AU$296
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (1,279 reviews)
"Great stay - two weeks of wonderful service and attentive front desk. It made my trip worth it!"

Reviewed on 18 Jul. 2025

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$323 per night from 9 Aug to 10 Aug
AU$323
9 Aug - 10 Aug
includes taxes & fees
8/10 Very Good! (2,092 reviews)
"Hotel is just ok but we were delayed all day on a flight got in at 1:00am and obviously missed our connection. So we had about 5 hours before catching a new flight the next morning and you can literally walk to and from the hotel to the departure area in 5 mins. Staff was very friendly and ..."

Reviewed on 17 Jul. 2025

Hilton Chicago O'Hare Airport
See all 3,038 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$807. 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

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
Grant Park

Grant Park

4.5/5(47 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

Activities

River tour boat in Chicago

Architecture River Tour

AU$75
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$69
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

AU$69
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
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.