Highland Vacations from $348

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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.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was $531, price is now $348 per person
$348
per person
Jun 14 - Jun 19
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (998 reviews)
I enjoyed my stay here. Clean and friendly environment

Reviewed on Apr 4, 2026

Holiday Inn Express & Suites Prospect Heights by IHG

Holiday Inn Express & Suites Prospect Heights by IHG

3 out of 5
Save 100% on your flight
Price was $591, price is now $389 per person
$389
per person
Jun 14 - Jun 19
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (929 reviews)
Good breakfast, could have more options for vegetarians, having croissants and breads everyday is not healthy for vegetarians

Reviewed on Mar 29, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,522, price is now $1,009 per person
$1,009
per person
Jun 21 - Jun 27
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Nice room, nice view of shops, within walking distance of the beach, shopping and places to dine.

Reviewed on Apr 4, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $912, price is now $606 per person
$606
per person
May 15 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Phenomenal nothing else to say top notch

Reviewed on Apr 5, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,410, price is now $952 per person
$952
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Beautiful rooms at an amazing location. Parking is terribly expensive though, and breakfast is not included. There is no mini fridge, so good luck saving leftovers to reduce expenses. There is also no swimming pool which I found weird for a place this elegant. Their main restaurant does not have good breakfast. Go for dinner or lunch and you will be very happy. But don't bother with breakfast, it's just a bunch of cheese and grease and it's unpleasant.

Reviewed on Apr 4, 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
$110 nightly
The price is $124 total per night from Apr 12 to Apr 13
$124 total
Apr 12 - Apr 13
Total with taxes and fees
8.4/10 Very Good! (1,007 reviews)
If check in is at 4 maybe consider having someone else at the desk as well. Had one older lady, tending to four different customers, all by herself.I felt so bad for her

Reviewed on Apr 4, 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
$122 nightly
The price is $140 total per night from Apr 12 to Apr 13
$140 total
Apr 12 - Apr 13
Total with taxes and fees
8.4/10 Very Good! (1,268 reviews)
Clean room , food good. I had a problem with a dog barking all 3 nights of our stay until 3am was very disappointed ☹️

Reviewed on Apr 4, 2026

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
$179 nightly
The price is $200 total per night from Apr 6 to Apr 7
$200 total
Apr 6 - Apr 7
Total with taxes and fees
9.4/10 Exceptional! (313 reviews)
All in all we had a wonderful stay

Reviewed on Apr 4, 2026

Wind Creek Southland Casino and Hotel
See all 921 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 $348 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.