Highland Vacations from NT$55,230

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The Latest Highland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Aug 7 - Aug 13
found 24 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
8.8/10 Excellent! (1,771 reviews)
Small rooms with very thin walls

Reviewed on 2025/6/18

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Aug 7 - Aug 13
found 24 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (1,613 reviews)
Great hotel with great staff.

Reviewed on 2025/6/20

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
Aug 7 - Aug 13
found 24 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.2/10 Wonderful! (1,749 reviews)
Great location, friendly staff, nice rooms!

Reviewed on 2025/6/21

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Aug 7 - Aug 13
found 24 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Beautiful property. Amazing customer service.

Reviewed on 2025/6/17

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
Aug 7 - Aug 13
found 24 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
I loved my stay at The Wit. It was a convenient walk to everything. Great location, great staff!

Reviewed on 2025/6/18

Find the Best Highland Vacation Packages

Highland Hotel Deals

Hilton Chicago/Oak Lawn
Hilton Chicago/Oak Lawn
3.5 out of 5
9333 S Cicero Ave, Oak Lawn, IL
Fully refundableReserve now, pay when you stay
The price is NT$3,993 per night from Jun 30 to Jul 1
NT$3,993
NT$4,591 total
Jun 30 - Jul 1
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"I like the location"

Reviewed on 2025/6/17

Hilton Chicago/Oak Lawn
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
3.5 out of 5
18501 Convention Center Drive, Tinley Park, IL
Fully refundable
The price is NT$2,746 per night from Jun 29 to Jun 30
NT$2,746
NT$3,299 total
Jun 29 - Jun 30
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"Great stay. Will stay on on next visit"

Reviewed on 2025/6/21

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
Holiday Inn Express & Suites Chicago - Oak Forest by IHG
Holiday Inn Express & Suites Chicago - Oak Forest by IHG
2.5 out of 5
4365 Frontage Rd, Oak Forest, IL
Fully refundable
The price is NT$3,612 per night from Jun 29 to Jun 30
NT$3,612
NT$4,226 total
Jun 29 - Jun 30
includes taxes & fees
9/10 Wonderful! (341 reviews)
"Staff was friendly and helpful. Clean room and public areas. Breakfast options were plentiful. Only downsize was the walls are to thin. Could hear doors opening, people talking, etc."

Reviewed on 2025/6/18

Holiday Inn Express & Suites Chicago - Oak Forest by IHG
See all 786 properties in Highland
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 vacation package cost?
Offering great value package deals from NT$55,230 on Expedia, you'll be surprised at how little a vacation to Highland costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Highland?
You can generally find lower rates and better availability in January, February and November. Explore our cheap Highland vacation packages and you could get some great off-season discounts.
How many days is enough for Highland?
With a well-planned schedule, you can easily hit the most popular Highland attractions in a few days. But if you want to venture off the beaten track or take day trips, think about booking your Highland vacation for longer.
How to find the best Highland package deals?
Use Expedia's handy filters to help you find some unbeatable Highland package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Highland package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Highland vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels individually. Better still, you can tailor your Highland getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Highland?
If you're considering a spontaneous Highland trip, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Highland?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the available activities will also help you decide when to visit Highland.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and dining out to flights and activities. Your hotel will probably be the biggest expense during your trip to Highland.
  3. Set the duration of your trip: Start by listing all the attractions you'd like to get to in Highland. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Highland vacation package.

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