Highland Holiday Deals

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Highland Holiday Package Deals

Bills, rent, work — isn't life hard enough? At lastminute.com.au, we can combine all your hotel bookings, airfares, hire cars and thrilling activities into a tidy package. You'll have more cash for Highland adventures and less paperwork to deal with!

How does a spare sound? That's what you could save if you book today.

Mix and match from 400 partner airlines and 282,000 hotels. With so many choices, you can craft a deal that suits your tastes and travelling style.

Think packages can't get any better? Challenge accepted. With our Price Pledge, if you find a lower price on your package or hotel within 24 hours of booking online, we'll match it by refunding you the difference.Terms and conditions apply.

Holidays in Highland

Been diagnosed with a bad case of the travel bug? Chillax — we've got the cure. Book a ticket to Highland and you'll feel a million bucks in no time!

It's located 930 kilometres west of United States of America's capital, Washington.

First Midwest Bank Amphitheatre is just 17 kilometres away in Homewood. This wonderful attraction is certainly worth the journey.

Sitting 45 kilometres to the north, North Avenue Beach is a great place to while away a few hours relaxing by the seaside. Montrose Beach is also home to some picturesque views. You'll discover this piece of coastline 50 kilometres to the north.

You'll find an assortment of striking natural sights just outside of Highland. Why not take off 35 kilometres to Indiana Dunes State Park? Alternatively, experience nature's artwork at Indiana Dunes National Lakeshore, 35 kilometres away.

Centennial Park is a tempting spot for a delicious picnic and a walk on a fine day. Remember to bring your camera!

What could be more fun than cheering yourself hoarse at a basketball game? Watch the Chicago Bulls bid for glory at United Center, located in Chicago, 40 kilometres away. Alternatively, get swept up in the exciting atmosphere of a live home game featuring the Chicago Blackhawks.

Take in the views from the chairlift at Raging Buffalo Snowboard Ski Park as you consider your next run. Along with Four Lakes Alpine Snowsports, this snow-dusted wonderland boasts some of the best skiing in the region.

What about stopping at South Shore Convention and Visitors Authority? It's a great place to spend some spare time.

Midway International Airport (MDW), the nearest airport, is 35 kilometres to the northwest from the middle of Highland. Pick a route, pack your bags and set an alarm — and make sure you don't hit the snooze button too many times!

Hotels in Highland

Planning to stay a few nights? You'll want to get in fast as there are just 17 Highland hotels on offer. So why put it off any longer? Let lastminute.com.au help you book today!

Want some hot tips? The Residence Inn By Marriott Chicago Southeast Hammond and Hampton Inn and Suites Munster are on par when it comes to great service and a comfortable night's rest.

Top hotels for your Highland holiday

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$261 per night from 14 May to 15 May
AU$261
14 May - 15 May
includes taxes & fees
Located in Hazel Crest (East Hazel Crest), Wind Creek Southland Casino and Hotel is within a 15-minute drive of Ravisloe Country Club and Tinley Park Convention ...
I don't like the fact that you allow kids at this property. They run around unsupervised, going to the pool. The property should be for people 21 and older!!

Reviewed on 12 May 2026

Opens in a new windowWind 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 AU$190 per night from 20 May to 21 May
AU$190
20 May - 21 May
includes taxes & fees
With a stay at DoubleTree by Hilton Chicago - Alsip in Alsip, you'll be near the airport, within a 15-minute drive of SeatGeek Stadium and Trinity Christian ...
Clean room with comfortable bed. No complimentary breakfast. No microwave in room. Pool closed. Parking was good. If there was a fitness room I couldn’t find it. Outside visiting area very convenient.

Reviewed on 11 May 2026

Opens in a new windowDoubleTree by Hilton Chicago - Alsip
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
The price is AU$209 per night from 14 May to 15 May
AU$209
14 May - 15 May
includes taxes & fees
In the heart of Chicago, Chicago Lake Shore Hotel is within a 5-minute drive of University of Chicago and Griffin Museum of Science and Industry.
This is an older 2 story property with great big refinished rooms with lake views. Daily attention to room turndown excellent! Front desk staff very nice. Location is wonderful with the highway close, biking path and water close, food a short walk, and museums a short drive. Parking is free. Downside ...

Reviewed on 11 May 2026

Opens in a new windowChicago Lake Shore Hotel
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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.

Top Picks

^Savings based on all package bookings made with Flight + Hotel on lastminute.com.au from January 1, 2019 to December 31, 2019, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.