Highland Vacations from ￥206,246

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The Latest Highland Vacation Packages

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

Arlo Chicago

4 out of 5
Downtown Chicago
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,749 reviews)
A good location, modern, clean and friendly staff.

Reviewed on Jun 19, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,609 reviews)
Beautiful spacious well thought room with no dust, beautiful views of the lake and river and buildings, perfect staff teams (front desk, bellboys, housekeeper team)! I will be back at the same room!

Reviewed on Jun 19, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
The customer service was top notch, everyone went above and beyond to make my stay an exceptional experience!! 5 Stars All around!!

Reviewed on Jun 10, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Beautiful property. Amazing customer service.

Reviewed on Jun 17, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (319 reviews)
I had no idea how nice this property would be! I had a full one-bedroom apartment and amazing view and amenities. 10/10, would stay again!

Reviewed on Jun 1, 2025

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 ￥19,604 per night from Jun 30 to Jul 1
￥19,604
￥22,541 total
Jun 30 - Jul 1
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"I like the location"

Reviewed on Jun 17, 2025

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 ￥13,485 per night from Jun 29 to Jun 30
￥13,485
￥16,196 total
Jun 29 - Jun 30
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"Front desk is always friendly, even helped and worked with me to get me checked in early. Rooms are always clean and great big space"

Reviewed on Jun 17, 2025

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 ￥17,736 per night from Jun 22 to Jun 23
￥17,736
￥20,748 total
Jun 22 - Jun 23
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 Jun 18, 2025

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 ￥206,246 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.