Highland Vacations from $575
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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.
Trump International Hotel & Tower Chicago
Downtown Chicago
$587
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
The Trump hotel is right in the middle of downtown, but it's on the quieter side of the river from the other hotels. It offers direct access to the river where you can join the architecture river tour and is overall quieter than the hotels on the other side of the river. The self parking is a bit of a tricky drive up very narrow and curving ramps. If you drive a Suburban or a Cybertruck, you might have difficulty.
Reviewed on Sep 29, 2026
Level Chicago – Old Town
Downtown Chicago
$741
per person
Oct 29 - Nov 2
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.
Reviewed on Sep 27, 2026
Highland Hotel Deals
The Cardinal Hotel
2205 Main St Highland IN
Fully refundableReserve now, pay when you stay
$219 nightly
$246 total
Sep 30 - Oct 1
Total with taxes and fees
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
$169 nightly
$199 total
Sep 30 - Oct 1
Total with taxes and fees
7/10 Good! (1,018 reviews)
"Good"
Reviewed on Sep 28, 2026
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
$169 nightly
$189 total
Oct 13 - Oct 14
Total with taxes and fees
9.4/10 Exceptional! (732 reviews)
"King bed was comfortable with nice pillows. The bathroom lights were push button behind the door, not convenient and no bathroom fan. Key card took a while to activate and actually work, staff assisted after several minutes at the elevator and rode up with is to ensure we were able to get in our ..."
Reviewed on Sep 29, 2026
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 $575 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?
- 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.
- 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.
- 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.
- 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.
- Combine your airfare and accommodations: After you've settled on your travel dates and duration, book the ideal Highland vacation package for you.
- 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.
