Highland Holidays from AU$1,198

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Your Highland Holiday

Put together a custom holiday package to Highland and get ready for your next great adventure. Consider staying in the neighbourhood of East Side, which is good for nature and walking, for a true taste of this interesting city. If sightseeing is on the agenda during your trip to Highland, check out major attractions like Hard Rock Casino Northern Indiana, Purdue University Northwest and Hammond Sportsplex & Community Centre. A few quick clicks is all it takes to build a customised Highland holiday on Expedia.

The Latest Highland Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
Price was AU$1,419, price is now AU$1,198 per person
AU$1,198
per person
26 Sept - 28 Sept
found 1 day ago
Return direct flight included
Orlando (MCO) to Chicago (ORD)
8.4/10 Very Good! (3,738 reviews)
Convenient to stay and walk around

Reviewed on 23 Aug. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$2,088, price is now AU$1,566 per person
AU$1,566
per person
26 Sept - 28 Sept
found 1 day ago
Return direct flight included
Orlando (MCO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug. 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,744, price is now AU$1,421 per person
AU$1,421
per person
26 Sept - 28 Sept
found 1 day ago
Return direct flight included
Orlando (MCO) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Will be coming back! Beautiful rooms and great staff.

Reviewed on 24 Aug. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was AU$1,835, price is now AU$1,498 per person
AU$1,498
per person
26 Sept - 28 Sept
found 1 day ago
Return direct flight included
Orlando (MCO) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug. 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was AU$1,744, price is now AU$1,501 per person
AU$1,501
per person
26 Sept - 28 Sept
found 1 day ago
Return direct flight included
Orlando (MCO) to Chicago (ORD)
9.4/10 Exceptional! (3,344 reviews)
I enjoyed the total experience of staying at this facility.

Reviewed on 22 Aug. 2025

Highland Holiday

Highland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Midway Intl. Airport (MDW)
Population
22,900
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Lake Street Beach, Mascot Hall Of Fame and Whihala Beach

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 AU$225 per night from 1 Sept to 2 Sept
AU$225
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,013 reviews)
"Nice"

Reviewed on 22 Aug. 2025

Hilton Chicago/Oak Lawn
Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
12801 South Cicero, Alsip, IL
Fully refundableReserve now, pay when you stay
The price is AU$163 per night from 2 Sept to 3 Sept
AU$163
2 Sept - 3 Sept
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"Our room was clean except for the sheets. I brought my own to sleep on, thankfully! However, the bathroom and again everything else in the room was clean. Friendly staff, and great hot breafast. You have to get there early to eat bevause the waffle mix goes fast. I will stay there again."

Reviewed on 22 Aug. 2025

Baymont by Wyndham 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 AU$122 per night from 7 Sept to 8 Sept
AU$122
7 Sept - 8 Sept
includes taxes & fees
6.4/10 (71 reviews)
"Clean remodeled rooms."

Reviewed on 15 Aug. 2025

Motel 6 - Chicago, IL
See all 844 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Highland holiday package cost?
Offering great value package deals from AU$1,198 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.