Highland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Highland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
CA $1,405
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Beautiful stay along the riverwalk. Pretty easy to get to public transportation as well as much to do within walking distance. The hotel was clean and well taken care of. We enjoyed to larger gym hotel with plenty of equipment.
Reviewed on Aug 11, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,370
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Overall the views were wonderful. The proximity was great. The room wasn’t clean. Bedding had stains on it. No one cleaned our room. No towels. Front desk was definitely not friendly. The elevator stopped working.
Reviewed on Aug 11, 2026
Ready to book your vacation to Highland?
Highland Hotel Deals
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
CA $228
CA $267 total
Sep 7 - Sep 8
includes taxes & fees
7/10 Good! (1,021 reviews)
"First off, I have to say the two staff members at the front desk at check-in and -out were some of the friendliest, most welcoming, helpful hotel personnel I've ever encountered. Truly, ever. I wouldn't even be writing this review if not for them. Give them a raise. The room was fine. Very accessible. ..."
Reviewed on Aug 10, 2026
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
CA $105
CA $123 total
Sep 7 - Sep 8
includes taxes & fees
7.2/10 Good! (438 reviews)
"Basic motel but it was clean, had what you needed, easy quick cheap option"
Reviewed on Aug 9, 2026
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
CA $165
CA $186 total
Sep 7 - Sep 8
includes taxes & fees
8.4/10 Very good! (1,186 reviews)
"Even though you are close to the highway, the room was quiet. Staff was extremely helpful and professional during our stay. Abundant free parking. We would happily stay there again"
Reviewed on Aug 10, 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.
What to do in Highland
Chicago Pass: Save up to 50 Percent - Includes 360 CHICAGO
CA $209
per adult
82% of travellers recommend
Frequently asked questions
How much does a Highland vacation package cost?
You'll find cheap prices from CA $1,062 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 travelling in January, February and November. You'll usually find lower prices on flights and accommodations during these months — ideal for budget-conscious travellers.
How many days is enough for Highland?
With a well-organized schedule, you can easily hit the most popular Highland sights in a handful of days. But if you'd like to venture off the beaten track or take day trips, think about booking your Highland vacation for longer.
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?
- 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.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
