Highland Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to SAR 390 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Highland Vacation Packages

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
The price is SAR 447 per night from Apr 13 to Apr 14
SAR 447
SAR 514 total
includes taxes & fees
13 Apr - 14 Apr
8/10 Very Good! (1,004 reviews)
"Always have a great stay at Hilton oak lawn"

Reviewed on 2 April 2025

Hilton Chicago/Oak Lawn
Hyatt Place Chicago-South/University Medical Center
Hyatt Place Chicago-South/University Medical Center
3 out of 5
5225 S Harper Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is SAR 567 per night from Apr 20 to Apr 21
SAR 567
SAR 665 total
includes taxes & fees
20 Apr - 21 Apr
8.8/10 Excellent! (1,003 reviews)
"Each time I have visited it has been a great stay. Hotel is clean, staff is personable and very friendly. The only disturbance was construction next to the hotel was loud and started before 7am breaking our sleep."

Reviewed on 4 April 2025

Hyatt Place Chicago-South/University Medical Center
Super 8 by Wyndham South Holland
Super 8 by Wyndham South Holland
2 out of 5
17225 Halsted St, South Holland, IL
Fully refundableReserve now, pay when you stay
The price is SAR 271 per night from Apr 13 to Apr 14
SAR 271
SAR 306 total
includes taxes & fees
13 Apr - 14 Apr
7.4/10 Good! (1,007 reviews)
"Great place and staff is cool"

Reviewed on 4 April 2025

Super 8 by Wyndham South Holland
See all 745 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.

Frequently asked questions

How much does a Highland vacation package cost?
Offering great value package deals 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?
You can generally find lower rates and better availability in January, February and November. Explore our cheap Highland vacation packages and you could get some great off-season discounts.
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 when to travel: Check your calendar and get your bags packed. Your preferred season and the available activities will also help you decide when to visit Highland.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and dining out to flights and activities. Your hotel will probably be the biggest expense during your trip to Highland.
  3. Set the duration of your trip: Start by listing all the attractions you’d like to get to in Highland. Then, estimate how long you’ll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Highland vacation package.