Highland Vacations from $368

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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.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $672, price is now $368 per person
$368
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (281 reviews)
From the time we came through the front door we were greeted with a smile can’t remember their names but very good customer service rooms were great housekeeping gave me what I needed everyone greeted us every time we enter the lobby area Mike an Ashley checked us out with smiles they took time and ask how was our stay very knowledgeable about the billing also breakfast was excellent everything and everyone was great Thank you Jacqueline Robinson

Reviewed on Oct 21, 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $999, price is now $514 per person
$514
per person
Dec 31 - Jan 3
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,195, price is now $633 per person
$633
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
It was very clean, quiet and a unique space. It was in walking distance of a lot of great restaurants. My husband loved the mattress. Great water pressure on the fourth floor.

Reviewed on Oct 17, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $788, price is now $418 per person
$418
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.

Reviewed on Oct 16, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $727, price is now $395 per person
$395
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Great hotel. Better coffee would be great

Reviewed on Oct 21, 2025

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Highland Hotel Deals

Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
9333 S Cicero Ave, Oak Lawn, IL
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $142 total per night from Oct 28 to Oct 29
$142 total
Oct 28 - Oct 29
Total with taxes and fees
8.2/10 Very Good! (1,081 reviews)
"Room was clean and quiet. Key card stopped working and was required to operate elevator. That was slightly inconvenient but overall an enjoyable stay."

Reviewed on Oct 18, 2025

Hilton Chicago/Oak Lawn
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $88 total per night from Oct 22 to Oct 23
$88 total
Oct 22 - Oct 23
Total with taxes and fees
6.6/10 (139 reviews)
"Everything was very nice even staff"

Reviewed on Oct 11, 2025

Motel 6 - Chicago, IL
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
777 Ameristar Blvd., East Chicago, IN
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $167 total per night from Oct 22 to Oct 23
$167 total
Oct 22 - Oct 23
Total with taxes and fees
8.4/10 Very Good! (1,027 reviews)
"This place was very comfortable. I love the neighboring beach, restaurants, and smoking room option. I only wish the rooms came equipped with microwaves."

Reviewed on Oct 19, 2025

Ameristar Casino Hotel East Chicago
See all 858 properties in Highland
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

How much does a Highland vacation package cost?
Offering great value package deals from $368 on Expedia, you'll be surprised at how little a vacation to Highland costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Highland?
If you'd like to book a cheap Highland vacation package, consider traveling in November, December and January. You'll usually find lower prices on accommodations and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Highland?
With a well-organized travel plan, you can easily hit the most popular Highland attractions in a handful of days. But if you'd like to discover hidden spots or go on day trips, consider booking your Highland vacation for longer.
How to find the best Highland package deals?
Use Expedia's handy filters to help you find some unbeatable Highland package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Highland package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Highland vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels individually. Better still, you can tailor your Highland getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Highland?
If you're considering a spontaneous Highland trip, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Highland?

  1. Choose the perfect time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to go to Highland.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to activities and airfares. Your hotel will probably be the largest expense during your trip to Highland.
  3. Discover Highland with our trip planning tool: Gain insights into the most popular attractions and best stays for your trip to Highland. You can also save your must-visit places, collaborate with friends and family and manage your plans in one place.
  4. Decide how many days away: Start by compiling a list of the sights and activities you want to get to in Highland. Then, estimate how long you'll need at each, along with any travel time.
  5. Combine your airfare and accommodations: After you've settled on your travel dates and duration, book the ideal Highland vacation package for you.
  6. Book activities and experiences ahead of time: Whether it's a ticket to a big attraction or a day trip in nature, you won't have to worry about missing out on Highland's best offerings. Find all the exciting things to do in Highland with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Highland vacation packages?
If you're like us, you love traveling the world but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Highland break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.