
Highland Vacations from $389
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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.

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $777, price is now $389 per person
$389
per person
Mar 11 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
A nice, clean hotel. Excellent breakfast.
Reviewed on Jan 15, 2026


Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,708, price is now $982 per person
$982
per person
Mar 12 - Mar 17
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.
Reviewed on Jan 5, 2026

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $816, price is now $472 per person
$472
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay.
Reviewed on Jan 12, 2026

The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $822, price is now $482 per person
$482
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
room was clean, comfortable, & staff were kind and welcoming
Reviewed on Jan 12, 2026
Highland Hotel Deals

DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $110 total per night from Jan 25 to Jan 26
$110 total
Jan 25 - Jan 26
Total with taxes and fees
8.2/10 Very Good! (1,011 reviews)
The room was very nice comfortable clean and stocked. Staff was very nice only inconvenience was the mini fridge did not work
Reviewed on Jan 10, 2026

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 Jan 22 to Jan 23
$131 total
Jan 22 - Jan 23
Total with taxes and fees
8.2/10 Very Good! (1,177 reviews)
Staff very friendly!
Reviewed on Jan 12, 2026

Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $163 total per night from Jan 19 to Jan 20
$163 total
Jan 19 - Jan 20
Total with taxes and fees
9.2/10 Wonderful! (226 reviews)
Everything
Reviewed on Jan 10, 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


















