Highland Vacations from ￥93,126
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
￥193,537
per person
Nov 25 - Nov 29
found 19 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is one of the best Trump properties I've been to.
I know Trump Hotels' bar is high, but this is on another level.
Obviously, being a landmark in Chicago, location is the best in Chicago.
There is a Langham property right next to it, but this is it.
Rooms are well maintained, and the restaurants were excellent.
I hope to visit again soon.
Reviewed on Oct 12, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
￥134,441
per person
Nov 25 - Nov 29
found 19 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Cet hôtel est tout simplement parfait. Tout est d'une propreté irréprochable, le buffet du matin compris dans le prix de la chambre est exceptionnel et varie tous les jours, Et que dire de l'emplacement, tout simplement idéal, au coeur de Chicago, au coin de selon moi la plus belle rue de Chicago le Michigan Avenue, à deux pas de la Chicago River. Je vous conseille fortement de faire le tour de bateau Architecture sur la rivière, c'est vraiment intéressant et ça va donnes une vue complètement différente de la ville. Chicago a été un énorme coup de cœur pour moi. Le seul bémol est que si vous y allez en vacances, mois ce fut pour affaire, prévoyez un budget car c'est assez dispendieux.
Reviewed on Oct 12, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
￥133,892
per person
Nov 25 - Nov 29
found 19 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Lovely hotel with a great location. Kind staff. Only slight disappointment is that the fan in our bathroom did not work so it got a bit foggy. But outside of that very small thing this place was perfect.
Reviewed on Oct 11, 2026
Find the Best Highland Vacation Packages
Highland Hotel Deals
The Cardinal Hotel
2205 Main St Highland IN
Fully refundableReserve now, pay when you stay
￥37,139
￥41,595 total
Oct 20 - Oct 21
includes taxes & fees
10/10 Exceptional! (15 reviews)
"Staff were really friendly and helpful. Definitely a beautiful place and would visit again."
Reviewed on Oct 11, 2026
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
￥28,353
￥31,750 total
Oct 14 - Oct 15
includes taxes & fees
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
￥25,171
￥29,547 total
Nov 1 - Nov 2
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 ￥93,126 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.
