Highland Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Highland Vacation Packages

Highland Hotel Deals

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
The price is SARĀ 747 per night from Jul 21 to Jul 22
SARĀ 747
SARĀ 877 total
21 Jul - 22 Jul
includes taxes & fees
7/10 Good! (1,009 reviews)
"Very clean rooms and the location was right across the street from Lake, Michigan, and within walking distance of several businesses"

Reviewed on 20 July 2026

Chicago Lake Shore Hotel
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
The price is SARĀ 553 per night from Jul 22 to Jul 23
SARĀ 553
SARĀ 620 total
22 Jul - 23 Jul
includes taxes & fees
9.4/10 Exceptional! (532 reviews)
"The room was extremely clean and the bed was very comfortable. The staff was very professional and helpful. Parking was great!"

Reviewed on 20 July 2026

Wind Creek Southland Casino and Hotel
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is SARĀ 335 per night from Aug 4 to Aug 5
SARĀ 335
SARĀ 393 total
4 Aug - 5 Aug
includes taxes & fees
7.2/10 Good! (409 reviews)
"Power was out in half the hotel, rooms are run down. Remodeled from the budget motel but nothing has changed maintenance ignored and prostitution going on."

Reviewed on 20 July 2026

Motel 6 - Chicago, IL
See all 905 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?
You'll find cheap prices on Expedia for your Highland break. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Highland costs.
What are the cheapest months to go to Highland?
If you'd like to score a cheap Highland vacation package, consider traveling in January, February and November. You'll usually find lower prices on flights and accommodations during these months ā€” ideal for budget-conscious travelers.
How to find the best Highland package deals?
Landing a cheap Highland package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Highland package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Highland vacation as a package?
You can enjoy significant savings on your Highland break by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to see some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Highland?
If you're planning a spontaneous Highland getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Highland?

  1. Choose when to go: Check your calendar and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to visit Highland.
  2. Set your budget: Factor in costs such as flights, food and transportation when working out how much to set aside for your trip to Highland. Then, choose a property that matches your budget, whether that's a wallet-friendly option or a deluxe getaway.
  3. Work out your trip length: Think about how much time you want to spend exploring Highland. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Highland vacation package that brings all your bookings together.