Highland Vacations from ￥461,740
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Highland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥461,740
per person
Nov 15 - Nov 20
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
Nice place and location, especially if you have a good room. It's expensive but you get good experiance
Reviewed on Aug 26, 2026
Swissotel - Chicago
Downtown Chicago
￥471,246
per person
Nov 15 - Nov 20
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Pros: Location is excellent. View was excellent. They upgraded my room from the 4th floor to the 28th floor at no extra cost. Cleaned when I requested.
Cons: Staff was a bit snooty snooty hoity toity. Didn't know I had to pay for parking so that cost more than I budgeted for, it was also an unnecessary hassle to do due to poor internet connection. Confusing amenity fees that I thought I was properly taking advantage of but toward the end felt was taking advantage of me to extract more money. I requested some items be brought up to our room only for staff to tell me I had to come down to the lobby myself to grab them.
Ultimately I can summarize the experience easily as its not worth what I paid for. Also no pool but thats more on me for not checking for that ahead of time.
Reviewed on Aug 26, 2026
The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
￥762,894
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
8/10 Very Good! (2,019 reviews)
Hair in the bed, impossible to talk to anyone because guest counter was packed and hotel is understaffed.
Reviewed on Aug 26, 2026
Find the Best Highland Vacation Packages
Highland Hotel Deals
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
￥24,995
￥29,342 total
Sep 7 - Sep 8
includes taxes & fees
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
￥12,169
￥14,285 total
Sep 13 - Sep 14
includes taxes & fees
Quality Inn & Suites Orland Park - Chicago
8800 W 159th St Orland Park IL
Fully refundable
￥14,226
￥15,931 total
Sep 20 - Sep 21
includes taxes & fees
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 ￥461,740 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?
- 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.
- 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.
- 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.
- 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.
