Highland Hills Vacations from NT$34,379

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The Latest Highland Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was NT$43,639, price is now NT$34,379 per person
NT$34,379
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Yes great Hotel everything was perfect

Reviewed on 2026/1/12

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was NT$53,482, price is now NT$35,706 per person
NT$35,706
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back!

Reviewed on 2026/1/11

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was NT$49,618, price is now NT$37,553 per person
NT$37,553
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Had an amazing stay. Just note, you need to ask for the room cleaning service, and its not for everyday. Overall really loved the place and hope to come back!

Reviewed on 2026/1/10

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was NT$45,588, price is now NT$35,001 per person
NT$35,001
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Clean room and amenities

Reviewed on 2026/1/8

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NT$44,455, price is now NT$34,811 per person
NT$34,811
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Great location, clean hotel

Reviewed on 2026/1/11

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 showing 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

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 NT$2,285 per night from Jan 15 to Jan 16
NT$2,285
NT$2,536 total
Jan 15 - Jan 16
includes taxes & fees
9/10 Wonderful! (2,478 reviews)
The Whole Hotel & its front desk, including our check-in & our Suite was A-1. Randy, Ernesto, Pat, Ken, Kim were Very Welcoming & Helpful. Breakfast & its staff & Housekeeping were Awesome.

Reviewed on 2026/1/7

SureStay Plus Hotel by Best Western Chicago Lombard
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
Fully refundable
The price is NT$3,385 per night from Jan 29 to Jan 30
NT$3,385
NT$3,974 total
Jan 29 - Jan 30
includes taxes & fees
8.8/10 Excellent! (2,104 reviews)
I love staying here. Great View. Staff is friendly.

Reviewed on 2026/1/10

Holiday Inn Chicago Dwtn - The Mart 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 NT$6,196 per night from Feb 6 to Feb 7
NT$6,196
NT$7,274 total
Feb 6 - Feb 7
includes taxes & fees
8.2/10 Very Good! (2,179 reviews)
We didn’t have breakfast included

Reviewed on 2026/1/11

Hilton Chicago O'Hare Airport
See all 3,301 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.

Frequently asked questions

How much does a Highland Hills vacation package cost?
We make it easy to travel somewhere new, with Highland Hills vacation packages starting from as low as NT$34,379. You'll have the flexibility to combine your favorite 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 vacation 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 vacation!
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 Center 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 vacation?
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 vacation package is the most convenient way to organize 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 vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our vacation 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 vacation package?
Don't worry if you're rethinking your Highland Hills vacation 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 realize 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

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.