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 AED 467 per night from Apr 27 to Apr 28
AED 467
AED 537 total
includes taxes & fees
27 Apr - 28 Apr
8/10 Very Good! (1,002 reviews)
"This was my second time this year at your hotel. Your staff is amazing. They all making me feel comfortable at all times. From the front desk to the front door and restaurant staff. Thank you for another wonderful experience. See you soon!"

Reviewed on 15 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 AED 694 per night from Apr 20 to Apr 21
AED 694
AED 815 total
includes taxes & fees
20 Apr - 21 Apr
8.8/10 Excellent! (1,002 reviews)
Family Friendly World Class Staff
"The staff was amazing! DJ went above and beyond to solve a booking issue created by the booking site. Brian made sure that check in was smooth and easy. The system hadn't saved the changes DJ established and Brian swooped in and fixed everything. The location was right off 94 so super easy access ..."

Reviewed on 13 April 2025

Hyatt Place Chicago-South/University Medical Center
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
3.5 out of 5
18501 Convention Center Drive, Tinley Park, IL
Fully refundable
The price is AED 342 per night from Apr 27 to Apr 28
AED 342
AED 410 total
includes taxes & fees
27 Apr - 28 Apr
8.8/10 Excellent! (1,003 reviews)
"Room not super clean, lots of hair on the bathroom floor and shower"

Reviewed on 14 April 2025

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
See all 743 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.