Orland Hills Vacation Packages

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Your Orland Hills Vacation

When you book a vacation package to Orland Hills, you can relax and enjoy your getaway knowing that all your travel arrangements are in order. Uncover the many delights of this vibrant city from your base in a neighborhood like Flossmoor, which is great for golfing. Like to explore? Hollywood Casino Amphitheatre, Odyssey Fun World and George Dunne National Golf Club are some of the top-rated places to visit during your trip to Orland Hills. A few quick clicks is all it takes to put together your ideal Orland Hills vacation on Expedia.

Top Holiday Package Deals in Orland Hills

Price found within the past 48 hours. Click for updated prices.
Delta Hotels by Marriott Chicago Willowbrook

Delta Hotels by Marriott Chicago Willowbrook

3 out of 5
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (429 reviews)
The staff was very friendly. Fast check-in and check-out with no issues! Second time staying here and will stay again!

Reviewed on Jul. 24, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Nice hotel with a great breakfast buffet

Reviewed on Jul. 25, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Large rooms, excellent view and location

Reviewed on Jul. 24, 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
The line to get coffee at the cafe downstairs was always 12 people deep. The staff was not very fast…

Reviewed on Jul. 21, 2025

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,584 reviews)
This is our 2nd time staying here and it is wonderful. Very nice staff, close to everything. Highly recommend!

Reviewed on Jul. 24, 2025

Orland Hills Hotel Deals

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 $125 per night from Aug 10 to Aug 11
CA $125
CA $140 total
Aug 10 - Aug 11
includes taxes & fees
7.2/10 Good! (1,011 reviews)
"Good place to stay"

Reviewed on Jul. 23, 2025

Quality Inn & Suites Orland Park - Chicago
Holiday Inn Chicago SW-Countryside ConfCtr by IHG

Holiday Inn Chicago SW-Countryside ConfCtr by IHG

3.5 out of 5
6201 Joliet Rd, Countryside, IL
Fully refundable
The price is CA $151 per night from Aug 10 to Aug 11
CA $151
CA $170 total
Aug 10 - Aug 11
includes taxes & fees
7.8/10 Good! (1,026 reviews)
"Room was clean good size and quiet. The pool is out of commission, the restaurant was closed when we needed to eat and we had no car to go somewhere else. Staff was polite and professional"

Reviewed on Jul. 22, 2025

Holiday Inn Chicago SW-Countryside ConfCtr by IHG
The Westin Chicago Lombard

The Westin Chicago Lombard

4 out of 5
70 Yorktown Center, Lombard, IL
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Aug 3 to Aug 4
CA $191
CA $212 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (1,013 reviews)
"Check in was not the greatest for me, the room was dirty, had hair and stuff in the bed. Went downstairs was given a “better & upgraded room” just for it to be dirtier than the previous and have trash on the nightstands. The third room, not only had hair in the bed and tub but the toilet was leaking. ..."

Reviewed on Jul. 24, 2025

The Westin Chicago Lombard
See all 957 properties in Orland Hills
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.
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Frequently asked questions

How much does an Orland Hills vacation package cost?
Browse and book everything in one place with our Orland Hills vacation packages, which start from just CA $620. Choose the flights and hotels that fit your travel plans. Then, add on a few experiences or tours for a one-of-a-kind getaway.
How do I get a cheap travel package to Orland Hills?
Browse and book everything in the one place with our Orland Hills vacation packages. You'll discover deals on hotels, flights and more that'll keep your pocketbook happy and your adventurous spirit busy. And, with more than 550 air carriers and 1,000,000 hotel options around the globe to select from, there are endless opportunities to mix and match.
Where should I stay in Orland Hills?
Choose a place within a stone's throw of Hollywood Casino Amphitheatre. This well-known sight is in the middle of the action and on the must-do lists of many urban explorers.
What are the top hotels in Orland Hills?
Quality Inn & Suites Orland Park - Chicago is one of Orland Hills's most sought-after hotels. Lock in a room here and you'll be able to rest easy knowing you're in excellent hands.
How far in advance should I book my Orland Hills vacation?
You'll be rewarded with the biggest variety and the cheapest prices by booking your Orland Hills adventure nice and early. Airlines usually publish flight tickets around a year in advance, so start your planning ASAP. Having said that, Expedia is committed to giving you the best bargains around, so it's always a good time to book your dream vacation!
What does an Expedia Orland Hills travel package include?
Hotels, flights and rental cars, or any combination of the three — it's totally up to you. Whether you're venturing to Orland Hills with the kids or adventuring with your friends, there's a package to fit your style and budget. Once you've made your booking, why not add on a couple of tours and experiences?
What should I know before booking an Orland Hills travel package?
Whether it's adventure or relaxation you're craving, an Orland Hills vacation package lets you organize your escape your way. Plus, you'll score great discounts when you combine your accommodations with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with an Orland Hills Expedia vacation package?
With a vacation package, you're in control. Whether you're eager to fly to Orland Hills in business or coach, simply pick from the available airline options. Expedia has access to more than 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Orland Hills vacation package?
Whether it's your hotel or flight, you can cancel and rebook it. Booked your Orland Hills vacation package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings older than that, you may incur a fee from your airline, hotel or car rental company. For further information, look up our Customer Service Portal. We'll help you each step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.