Highland Holidays from AU$2,184
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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.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was AU$3,172, price is now AU$2,184 per person
AU$2,184
per person
20 Oct - 26 Oct
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
I had an amazing experience here! The staff—from valet to front desk to restaurant—was incredibly courteous, and Nate at the bar was a standout! My room was spotless, housekeeping was proactive, and guest services were top-tier.
The area around the hotel is packed with restaurants, bars, and convenience stores—super walkable and fun.
Only two minor cons: the terrace closes at 10 PM (wish it stayed open later), and the pool was closed during my visit.
Still, this place blew me away. Highly recommend!
Reviewed on 31 Aug. 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was AU$4,113, price is now AU$2,534 per person
AU$2,534
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,192 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
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$5,610, price is now AU$3,478 per person
AU$3,478
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on 29 Aug. 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$5,537, price is now AU$3,571 per person
AU$3,571
per person
20 Oct - 26 Oct
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on 31 Aug. 2025
Level Chicago – Old Town
Downtown Chicago
Price was AU$3,524, price is now AU$2,340 per person
AU$2,340
per person
20 Oct - 26 Oct
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on 27 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
9333 S Cicero Ave, Oak Lawn, IL
Fully refundableReserve now, pay when you stay
The price is AU$224 per night from 14 Sept to 15 Sept
AU$224
14 Sept - 15 Sept
includes taxes & fees
Baymont by Wyndham Chicago/Alsip
12801 South Cicero, Alsip, IL
Fully refundableReserve now, pay when you stay
The price is AU$154 per night from 7 Sept to 8 Sept
AU$154
7 Sept - 8 Sept
includes taxes & fees
Motel 6 - Chicago, IL
10022 South Halsted Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$121 per night from 14 Sept to 15 Sept
AU$121
14 Sept - 15 Sept
includes taxes & fees
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.