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.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,436
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is an elegant and high class facility with warm service and hospitality stuff
Centrally located on North River north bank.
The room is big and spacious overlooking the river.
We loved our stay.
The concierge gave us a great tips and services
Recommend by all means.
Reviewed on Oct 2, 2026
The Peninsula Chicago
Downtown Chicago
CA $2,564
per person
Dec 13 - Dec 18
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class
Reviewed on Oct 1, 2026
The Ritz-Carlton, Chicago
Downtown Chicago
CA $1,676
per person
Dec 13 - Dec 18
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.
Reviewed on Sep 24, 2026
Level Chicago – Old Town
Downtown Chicago
CA $1,118
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.
Reviewed on Sep 27, 2026
Ready to book your vacation to Highland?
Highland Hotel Deals
The Cardinal Hotel
2205 Main St Highland IN
Fully refundableReserve now, pay when you stay
CA $319
CA $357 total
Nov 2 - Nov 3
includes taxes & fees
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
CA $192
CA $226 total
Nov 1 - Nov 2
includes taxes & fees
7/10 Good! (1,000 reviews)
"Everything was clean they are busy updating this hotel. I like to location close to the hospital and free parking."
Reviewed on Oct 1, 2026
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
CA $222
CA $248 total
Oct 14 - Oct 15
includes taxes & fees
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 $208
per adult
82% of travellers recommend
Frequently asked questions
How much does a Highland vacation package cost?
You'll find cheap prices from CA $882 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.
