
Highland Vacations from $196
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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.

Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $365, price is now $196 per person
$196
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in.
Reviewed on Nov 25, 2025


Level Chicago – Old Town
Downtown Chicago
Price was $680, price is now $336 per person
$336
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views.
Reviewed on Dec 3, 2025

The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $587, price is now $316 per person
$316
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.
Reviewed on Nov 26, 2025

Highland Hotel Deals

Hilton Chicago/Oak Lawn
9333 S Cicero Ave Oak Lawn IL
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $145 total per night from Dec 29 to Dec 30
$145 total
Dec 29 - Dec 30
Total with taxes and fees
8.2/10 Very Good! (1,140 reviews)
Staff was very friendly, the hotel was very clean. We liked that we didn’t have to leave the hotel to get something to eat, the food was delicious and reasonably priced.
Reviewed on Nov 26, 2025

Ameristar Casino Hotel East Chicago
777 Ameristar Blvd. East Chicago IN
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $137 total per night from Dec 4 to Dec 5
$137 total
Dec 4 - Dec 5
Total with taxes and fees
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 Nov 29, 2025

Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $94 total per night from Dec 4 to Dec 5
$94 total
Dec 4 - Dec 5
Total with taxes and fees
6.8/10 (186 reviews)
Grest
Reviewed on Nov 25, 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.
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.



















