Highland Holidays from AU$274
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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 Orrington / Evanston
Downtown Evanston
Price was AU$382, price is now AU$274 per person
AU$274
per person
10 Jan - 12 Jan
found 1 day ago
Return flight included
Dallas (DFW) to Chicago (ORD)
7.6/10 Good! (1,002 reviews)
Clean rooms, great location in Evanston near the university. Helpful staff.
Reviewed on 17 Nov 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$849, price is now AU$558 per person
AU$558
per person
10 Jan - 12 Jan
found 1 day ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It's always perfection at the Trump. King suite with Lake view is the ultimate
Reviewed on 2 Dec 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was AU$475, price is now AU$328 per person
AU$328
per person
10 Jan - 12 Jan
found 1 day ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city
Reviewed on 26 Nov 2025
Hotel Chicago Downtown, Autograph Collection by Marriott
Downtown Chicago
Price was AU$427, price is now AU$300 per person
AU$300
per person
10 Jan - 12 Jan
found 1 day ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
Staff were very pleasant and helpful. We will definitely be back.
Reviewed on 26 Nov 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$220 per night from 29 Dec to 30 Dec
AU$220
29 Dec - 30 Dec
includes taxes & fees
8.2/10 Very Good! (1,138 reviews)
Room was nice staff was unfamiliar with the charging stations for my rental car but overall room was nice
Reviewed on 3 Dec 2025
Ameristar Casino Hotel East Chicago
777 Ameristar Blvd. East Chicago IN
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (1,025 reviews)
Morning staff was excellent. The night staff not so much. One of them even hung up on me when I called down to ask a question. Other than that, I HIGHLY recommend this hotel. Cleaning staff was very friendly.
Reviewed on 29 Nov 2025
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$128 per night from 18 Dec to 19 Dec
AU$128
18 Dec - 19 Dec
includes taxes & fees
6.8/10 (186 reviews)
Grest
Reviewed on 25 Nov 2025
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.
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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.
