Highland Vacations from $247

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Your Highland Vacation

Come and experience this amazing city for yourself with a Highland vacation package. Consider basing yourself in the neighborhood of East Side, which is good for nature and walking, and your time here will be nothing short of unforgettable. Make your trip to Highland even more fulfilling by going sightseeing. Hard Rock Casino Northern Indiana, Purdue University Northwest and Hammond Sportsplex & Community Center are among the popular attractions you'll want to explore. Whoever you're taking time off with and whatever your budget, your ultimate Highland vacation is only clicks away with Expedia.

The Latest Highland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,028 reviews)
Had everything I needed in walking distance, felt like the Hotel had everything I needed.

Reviewed on May 29, 2024

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 25 - Aug 29
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,001 reviews)
They didn’t have free wifi

Reviewed on May 28, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (208 reviews)
Loved all the neighborhood dogs & farmers market

Reviewed on May 20, 2024

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 25 - Aug 29
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,136 reviews)
The hotel is beautifully furnished. It is clean. The staff members are kind and helpful. The decor is a mix of The Continental (John Wick) and The Great Gatsby. Highly recommend this hotel.

Reviewed on Jun 1, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 18 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,200 reviews)
The spa was underwhelming. Everything else was great.

Reviewed on Jun 1, 2024

Highland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Midway Intl. Airport (MDW)
Population
22,900
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Whihala Beach, Lake Street Beach and Theatre at the Center

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 $51 per night from Jun 17 to Jun 18
$51
$65 total
includes taxes & fees
Jun 17 - Jun 18
4.6/10 (373 reviews)
"Nice"

Reviewed on May 15, 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 $85 per night from Jun 23 to Jun 24
$85
$96 total
includes taxes & fees
Jun 23 - Jun 24
7.2/10 Good! (890 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 $127 per night from Jun 9 to Jun 10
$127
$146 total
includes taxes & fees
Jun 9 - Jun 10
7.8/10 Good! (976 reviews)
"The water is being turned off at 10:00pm not back on until 5:00 am so I guess I have to not take a shower tonight smh"

Reviewed on May 30, 2024

Hilton Chicago/Oak Lawn
See all 729 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

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Highland vacation package cost?
From as little as $247. 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.