Highland Holidays

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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.

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

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
The price is AU$334 per night from 10 Aug to 11 Aug
AU$334
10 Aug - 11 Aug
includes taxes & fees
7/10 Good! (1,016 reviews)
"The room was clean and bed was a little stiff the air conditioner stunk a little"

Reviewed on 23 July 2026

Chicago Lake Shore Hotel
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 AU$224 per night from 27 July to 28 July
AU$224
27 July - 28 July
includes taxes & fees
9.4/10 Exceptional! (545 reviews)
"T"

Reviewed on 23 July 2026

Wind Creek Southland Casino and Hotel
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$151 per night from 17 Aug to 18 Aug
AU$151
17 Aug - 18 Aug
includes taxes & fees
7.2/10 Good! (411 reviews)
"everyone was helpful and kind. this was suppposedly a rough location on the south side of chicago- even though i was the only white person, everyone was kind adn considerate"

Reviewed on 22 July 2026

Motel 6 - Chicago, IL
See all 906 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

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

AU$216
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.

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