Highland Hills Vacations from NT$33,582

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The Latest Highland Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4 out of 5
Downtown Chicago
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.6/10 Exceptional! (1,005 reviews)
Comfortable bed and walkable but rooms can be noisy for outside noises

Reviewed on 2025/8/10

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Amazing property well worth the money

Reviewed on 2025/8/11

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 2025/8/10

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
We enjoyed the rooftop dining--the view is terrific, especially after dark. Excellent location on Michigan Ave near restaurants, shopping and museums. Did the valet parking and it worked well for us. The service was all around excellent including checkin/checkout, in room dining service (we did breakfast), concierge, baggage help and valet . They were able to give us a late check out so we could fit in an architectural boat tour and then kept our luggage all day until evening so we could squeeze more out of this long weekend trip to the Windy City. The hotel is clean, stylish and service is top rate. I would highly recommend this hotel.

Reviewed on 2025/8/11

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 2025/7/27

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$2,288 per night from Aug 13 to Aug 14
NT$2,288
NT$2,540 total
Aug 13 - Aug 14
includes taxes & fees
8.8/10 Excellent! (2,176 reviews)
"Room needed updating."

Reviewed on 2025/8/9

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 NT$4,248 per night from Aug 24 to Aug 25
NT$4,248
NT$4,987 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,367 reviews)
"The staff was absolutely wonderful. My friend and I were in town for a concert, and the staff were so kind to let us store our stuff in the hotel until we were able to check in, and before we were able to get on our train home."

Reviewed on 2025/8/11

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 NT$5,363 per night from Sep 5 to Sep 6
NT$5,363
NT$6,295 total
Sep 5 - Sep 6
includes taxes & fees
8/10 Very Good! (2,086 reviews)
"The room was comfortable and very quiet despite the proximity to the airport. I would have preferred a queen size bed, but the only available option was a double."

Reviewed on 2025/8/9

Hilton Chicago O'Hare Airport
See all 3,053 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$33,582. 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.