Highland Vacations

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Find the Best Highland Vacation Packages

Highland Hotel Deals

Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
The price is NT$4,804 per night from Aug 9 to Aug 10
NT$4,804
NT$5,380 total
Aug 9 - Aug 10
includes taxes & fees
9.4/10 Exceptional! (505 reviews)
"Fun place to stay"

Reviewed on 2026/7/14

Wind Creek Southland Casino and Hotel
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
The price is NT$4,201 per night from Aug 13 to Aug 14
NT$4,201
NT$4,747 total
Aug 13 - Aug 14
includes taxes & fees
8.4/10 Very Good! (1,139 reviews)
"My stay was overall pleasant and convenient, especially with the reliable and punctual airport shuttle service. However, the hotel is starting to show its age, with the carpets looking quite worn in some areas. It was a good experience. I would rebook. Thank you."

Reviewed on 2026/7/13

DoubleTree by Hilton Chicago - Alsip
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$2,869 per night from Aug 4 to Aug 5
NT$2,869
NT$3,368 total
Aug 4 - Aug 5
includes taxes & fees
7.4/10 Good! (399 reviews)
"I Didn't like the room I had at my Stay on July 12th through July 23 at 11am at motel 6. They need some repairs on some of they rooms.But they do have some rooms that are Okay ."

Reviewed on 2026/7/13

Motel 6 - Chicago, IL
See all 905 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 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.

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