Highland Vacations

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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 15 to Apr 16
SAR 447
SAR 515 total
includes taxes & fees
15 Apr - 16 Apr
8/10 Very Good! (942 reviews)
"I felt very safe. Although I personally didn’t think it was in a bad area, they had security guards in the parking lots. Extra security measure where you had to have your room card to get the elevator up to your floor which I thought was nice. Room was nice, very clean and quiet. I’d stay there ..."

Reviewed on 8 April 2025

Hilton Chicago/Oak Lawn
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 287 per night from Apr 23 to Apr 24
SAR 287
SAR 324 total
includes taxes & fees
23 Apr - 24 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
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 16 to Apr 17
SAR 567
SAR 665 total
includes taxes & fees
16 Apr - 17 Apr
8.8/10 Excellent! (1,007 reviews)
"We had a great stay. The rooms were clean and quiet and the staff was very helpful."

Reviewed on 4 April 2025

Hyatt Place Chicago-South/University Medical Center
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.