Highland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $775 when you book a flight and hotel together*
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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.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
per person
Aug. 10 - Aug. 13
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,004 reviews)
Perfect area to go shopping, check out tourist attractions, or relax at the beach. Very convenient area to head to Lakefront Trail as well for a morning run. Staff was helpful and friendly during every interaction. I really loved all the benefits you received through the destination fee. Property was clean and attentive. In a very walkable area and close to public transportation.

Reviewed on Jun. 3, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 21 - Aug. 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTZ) to Chicago (ORD)
8.8/10 Excellent! (208 reviews)
The staff here is amazing and so helpful. Loved my stay here.

Reviewed on Jun. 6, 2024

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
per person
Aug. 10 - Aug. 13
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,007 reviews)
Well kept, great location and friendly staff!

Reviewed on May 31, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Aug. 10 - Aug. 13
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,212 reviews)
Property is 5 star all the way. Staff is excellent. Restaurant is 5 star as well.

Reviewed on Jun. 6, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 25 - Aug. 29
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.2/10 Wonderful! (97 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

Highland Hotel Deals

Econo Lodge
Econo Lodge
2 out of 5
17301 S Halsted St, Building B, South Holland, IL
Fully refundableReserve now, pay when you stay
The price is CA $74 per night from Jun. 25 to Jun. 26
CA $74
CA $94 total
includes taxes & fees
Jun 25 - Jun 26
4.6/10 (380 reviews)
"Great customer service bad ratchet room"

Reviewed on May 31, 2024

Econo Lodge
Quality Inn & Suites Orland Park - Chicago
Quality Inn & Suites Orland Park - Chicago
2.5 out of 5
8800 W 159th St, Orland Park, IL
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Jun. 23 to Jun. 24
CA $115
CA $129 total
includes taxes & fees
Jun 23 - Jun 24
7.2/10 Good! (893 reviews)
"Nice place to stay"

Reviewed on May 28, 2024

Quality Inn & Suites Orland Park - Chicago
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 CA $174 per night from Jun. 19 to Jun. 20
CA $174
CA $200 total
includes taxes & fees
Jun 19 - Jun 20
7.8/10 Good! (1,006 reviews)
"We enjoyed the city view from our 10th floor room. We were in Chicago from out of town and this location was convenient and easy to find."

Reviewed on Jun. 3, 2024

Hilton Chicago/Oak Lawn
See all 735 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Highland vacation package cost?
From as little as CA $741. Yes, you read that correctly. Our Highland packages are the easiest way to make your dollar go further. Combine your preferred hotels, flights and car rentals and get out and explore this fabulous destination.
How do I get a cheap travel package to Highland?
Browse and lock in everything all in one place with our Highland vacation packages. We have incredible bargains on hotels, flights and more that’ll keep your pocket happy and your sense of adventure alive. And, with more than 550 airlines and 1,000,000 properties worldwide to choose from, you have countless opportunities to mix and match as you want.
Where should I stay in Highland?
Stay where the action happens. Many travelers favor hotels in the vicinity of popular attractions, such as Hard Rock Casino Northern Indiana, Purdue University Northwest and South Shore Convention and Visitors Authority.
How far in advance should I book my Highland vacation?
Browse Expedia to compare international fares as soon as possible. You can generally purchase a ticket up to a year in advance. If you don’t see your preferred air carrier, or you’re booking late, don’t despair. Low prices to Highland sometimes occur a few weeks before departure.
What does an Expedia Highland travel package include?
Flights, hotels and a cool set of wheels for your road trip adventures. Simply select your preferred bundle and gain access to great discounts. Once you’ve made your booking, add on a couple of tours and experiences and watch your savings grow. When it comes to creating your Highland trip, you’re the boss!
What should I know before booking a Highland travel package?
When you book your flights, hotels and car rentals together, you’ll be rewarded with awesome discounts. Whether you’re planning a beach break in a villa or want to stay in an upscale city hotel, Expedia will help make it happen.
Can I choose my airline with a Highland Expedia vacation package?
Expedia offers access to more than 550 partner airlines worldwide, so you sure can! Just select your preferred carrier and put together your ideal Highland escape.
If I'm not able to travel, can I cancel my Highland vacation package?
Yes you can, and we’ll help you every step of the way. You may be able to cancel or change your Highland vacation package for free if you booked in the last 24 hours. But you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If life gets in the way of your vacation, look up our Customer Service Portal for further information.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.