Highland Holidays

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Highland Holiday

Our pick of the best Highland Hotel Deals

Econo Lodge South Holland - Chicago Southland

Econo Lodge South Holland - Chicago Southland

2 out of 5
17301 S Halsted St, Building B South Holland IL
Fully refundableReserve now, pay when you stay
The price is NZ$126 per night from 23 July to 24 July
NZ$126
23 July - 24 July
includes taxes & fees
6.2/10 (831 reviews)
"You get what you pay for. If you just need a okay play to lay your head it’s cool. Got twins bed instead of queens though."

Reviewed on 5 July 2026

Econo Lodge South Holland - Chicago Southland
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$178 per night from 4 Aug to 5 Aug
NZ$178
4 Aug - 5 Aug
includes taxes & fees
7.4/10 Good! (390 reviews)
"If you want a cheap and affordable room. Motel 6 is the best option to go with. Clean room, helpful staff. Only downside was the ice machine was out of order for some reason."

Reviewed on 5 July 2026

Motel 6 - Chicago, IL
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 NZ$281 per night from 13 July to 14 July
NZ$281
13 July - 14 July
includes taxes & fees
9.4/10 Exceptional! (485 reviews)
"Love this place and will be back very soon."

Reviewed on 5 July 2026

Wind Creek Southland Casino and Hotel
See all 898 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.

What to do in Highland

Chicago Pass: Save up to 50 Percent - Includes 360 Chicago

Chicago Pass: Save up to 50 Percent - Includes 360 CHICAGO

NZ$228
per adult
82% of travellers recommend
Chicago Pass: Save up to 50 Percent - Includes 360 CHICAGO
See all activities in Highland

Frequently asked questions

How much does a Highland holiday package cost?
Offering great value package deals 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.

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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.