Highland Holidays from NZ$1,675

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The Latest Highland Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Hotel Riu Plaza Chicago
Thompson Chicago, by Hyatt
LondonHouse Chicago, Curio Collection by Hilton
Trump International Hotel & Tower Chicago

Highland Holiday

Our pick of the best 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 NZ$259 per night from 2 July to 3 July
NZ$259
2 July - 3 July
includes taxes & fees
8/10 Very Good! (1,007 reviews)
"I like the location"

Reviewed on 17 Jun. 2025

Hilton Chicago/Oak Lawn
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 NZ$140 per night from 10 July to 11 July
NZ$140
10 July - 11 July
includes taxes & fees
5.2/10 (23 reviews)
"Dirty"

Reviewed on 23 Jun. 2025

Motel 6 - Chicago, IL
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 refundableReserve now, pay when you stay
The price is NZ$159 per night from 29 June to 30 June
NZ$159
29 June - 30 June
includes taxes & fees
8.8/10 Excellent! (1,013 reviews)
"Quick check in process, awesome check in people. Slower elevators, but one was being serviced and there was a sign to use the staff service elevators. Rooms were clean and amazing."

Reviewed on 23 Jun. 2025

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
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 holiday package cost?
Offering great value package deals from NZ$1,675 on Expedia, you'll be surprised at how little a holiday to Highland costs! Expedia's packages simplify travel planning and maximise 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 holiday 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 holiday 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 holiday package as early as possible.
Is it cheaper to book a Highland holiday as a package?
An Expedia holiday 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 holiday 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 personalised Highland holiday package.

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