Highland Vacations from $372

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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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $731, price is now $372 per person
$372
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on Oct 20, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $3,682, price is now $1,112 per person
$1,112
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,070 reviews)
Great trip! Will stay again.

Reviewed on Nov 2, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,015, price is now $479 per person
$479
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
We loved the Pendry!

Reviewed on Oct 27, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $2,124, price is now $1,032 per person
$1,032
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
Really cool modern space

Reviewed on Nov 4, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $3,683, price is now $1,835 per person
$1,835
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. The deep soaking bathtub was smaller in scale than one would expect, and more specifically the shower head is set far too low for those of us who are six feet or taller. I would recommend this property.

Reviewed on Nov 3, 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
$127 nightly
The price is $146 total per night from Nov 16 to Nov 17
$146 total
Nov 16 - Nov 17
Total with taxes and fees
8.2/10 Very Good! (1,102 reviews)
Staff was great! The rooms, toilets and hotel should be updated. The rooms are nice, but need some repairs and modernizations.

Reviewed on Nov 2, 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 Nov 6 to Nov 7
$88 total
Nov 6 - Nov 7
Total with taxes and fees
6.6/10 (150 reviews)
Great hotel, not so great area
We booked 2 rooms here for a concert. The area around it is sketchy BUT the hotel makes you feel safe once in the room. Clean and decently quiet considering there were locals that were outside all night. Our taxi driver almost wouldnt take us to our hotel because the area is not the safest. But hotel-wise ...

Reviewed on Oct 27, 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
$111 nightly
The price is $124 total per night from Nov 6 to Nov 7
$124 total
Nov 6 - Nov 7
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
The room was perfect! Clean, spacious and overall very good! The employees also so nice!

Reviewed on Nov 2, 2025

Ameristar Casino Hotel East Chicago
See all 861 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 $372 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.