Highland Vacations from $259

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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

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $446, price is now $259 per person
$259
per person
Apr 16 - Apr 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Great location right off of Michigan Ave. They have a very good breakfast, that included almost everything you could want. It was very popular and packed with people. One negative, it felt like it was a cafeteria and not a relaxing place to sit down, relax and enjoy.

Reviewed on Mar 9, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was $1,462, price is now $892 per person
$892
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,613 reviews)
Every thing was amazing the staff was friendly and helpful shops and everything was close by I loved it thank you again

Reviewed on Mar 9, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,921, price is now $1,215 per person
$1,215
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,070 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.

Reviewed on Mar 3, 2026

Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Price was $449, price is now $289 per person
$289
per person
May 19 - May 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8/10 Very Good! (503 reviews)
Pool was out of commission. Front desk was welcoming.

Reviewed on Mar 5, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,311, price is now $858 per person
$858
per person
Jun 4 - Jun 8
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Room was nice and clean, decent view. Perfect location. Close to shopping and nice restaurants. Staff was amazing; Myron in particular was so kind and accommodating.

Reviewed on Mar 8, 2026

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Highland Hotel Deals

DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $115 total per night from Mar 22 to Mar 23
$115 total
Mar 22 - Mar 23
Total with taxes and fees
8.4/10 Very Good! (1,010 reviews)
The room was fine for what we needed - a place to stay before an early flight. I wouldn’t have wanted to stay any longer, it was a bit worn, carpet especially and the bed uncomfortable. The “handicap accessible “ (which we didn’t need was not great, no wheelchair would fit with the “closet” and the ...

Reviewed on Mar 9, 2026

DoubleTree by Hilton Chicago - Alsip
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
$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
Hilton Chicago/Oak Lawn
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $170 total per night from Mar 11 to Mar 12
$170 total
Mar 11 - Mar 12
Total with taxes and fees
9.4/10 Exceptional! (278 reviews)
Very clean inside and out.

Reviewed on Mar 7, 2026

Wind Creek Southland Casino and Hotel
See all 918 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 $259 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.