
Highland Vacations from $397
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Your Highland Vacation
Spend less time travel planning and more time having exciting adventures with a Highland vacation package. The neighborhood of East Side, which is good for nature and walking, makes an excellent base for your city break. Like to get out and explore? Hard Rock Casino Northern Indiana, Purdue University Northwest and Hammond Sportsplex & Community Center are three of the leading places to visit during your trip to Highland. Don't delay your visit to this destination any longer. Your ultimate Highland vacation is only a few clicks away with Expedia.
The Latest Highland vacation packages
Price found within the past 48 hours. Click for updated prices.

Hilton Chicago O'Hare Airport
O'Hare
Price was $627, price is now $397 per person
$397
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,217 reviews)
Had a steak and ribs at the restaurant downstairs and both were delicious
Reviewed on Mar 1, 2026

La Banque Hotel
Price was $759, price is now $419 per person
$419
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (467 reviews)
Room was amazing and beautiful and comfortable
Only issue was when we arrived they had a plumbing issue and the whole place smelled horrific like a sewer. We didn’t go eat at the restaurant because the smell made us nauseous
Reviewed on Mar 1, 2026


The Wade
Downtown Chicago
Save 100% on your flight
Price was $950, price is now $542 per person
$542
per person
May 10 - May 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,705 reviews)
My stay at The Wade overall was pretty good. I booked here because it has a pool, and I thought I would have a nice view (city view). The view wasn’t available, I was on the 27th floor and only had a view of the roof of other buildings, and other apartments. I kept the window covered for the most part. The pool was unkept in my opinion, I didn’t feel comfortable with the dirt ring on the white tile that surrounded the pool, and the water looked and felt pretty grimy, I felt it needed to be serviced. Though my main attractions to this location were not fulfilled it was very quiet on my floor, the cleaning crew were very polite and generous, and the valet was very friendly and always gave me great service despite it being very busy over the course of my stay.
Reviewed on Mar 2, 2026

Pendry Chicago
Downtown Chicago
Price was $1,060, price is now $678 per person
$678
per person
May 18 - May 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,136 reviews)
Front desk staff are gems! They knew my name after 1 interaction and were very attentive. The room amenities were very nice-- espresso, bottled water, chocolates, steamer, toiletries.
Reviewed on Mar 1, 2026
Highland Hotel Deals

Hilton Chicago/Oak Lawn
9333 S Cicero Ave Oak Lawn IL
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $131 total per night from Mar 16 to Mar 17
$131 total
Mar 16 - Mar 17
Total with taxes and fees
8.4/10 Very Good! (1,235 reviews)
We love this location and stay here whenever we’re in town.
Reviewed on Mar 5, 2026

DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $115 total per night from Mar 29 to Mar 30
$115 total
Mar 29 - Mar 30
Total with taxes and fees
8.4/10 Very Good! (1,006 reviews)
Great shuttle driver. Didn't use gym.
Reviewed on Mar 2, 2026

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
18501 Convention Center Drive Tinley Park IL
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $104 total per night from Mar 9 to Mar 10
$104 total
Mar 9 - Mar 10
Total with taxes and fees
9/10 Wonderful! (1,233 reviews)
Clean room with a very comfortable bed
Reviewed on Mar 5, 2026
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.
Find the Best Highland Vacation Packages
Highland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Midway Intl. Airport (MDW) |
Population | 22,900 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Whihala Beach, Lake Street Beach and Theatre at the Center |
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Frequently asked questions
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