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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $854, price is now CA $550 per person
CA $550
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Perfect place in the Loop. Customer service was perfect on all fronts.

Reviewed on Sep 9, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,784, price is now CA $1,121 per person
CA $1,121
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
We picked the Trump Hotel-Chicago to celebrate our 35th Wedding Anniversary mainly for the location and the amenities. The hotel EXCEEDED our expectations in every way. (1) The staff is so warm, kind, compassionate and extremely professional in such a friendly down-to-earth way. (2) The property itself is immaculate. (3) The amenities: Terrace 16- the view will take your breath away! The food/cocktails were fabulous as was the service. (3) Pablo - Director of Rooms, Curtis -Concierge were off the charts fabulous. I wish I could remember all the staff names that went out of their way to make our weekend so special. I cannot wait to stay here again. As another reviewer said: put any political opinions aside and treat yourself to a stay here. YOU WILL LOVE IT. (There is no political aura here...only a fantastic team that wants you to enjoy your stay and they go out of their way to make sure you do).

Reviewed on Sep 8, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,759, price is now CA $1,142 per person
CA $1,142
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (679 reviews)
Rooms could be updated. Staff was under trained. Amenities very nice, used family room daily with our toddler. Pool deck very modern and new

Reviewed on Sep 8, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $2,069, price is now CA $1,368 per person
CA $1,368
per person
Oct 23 - Oct 26
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug 12, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,016, price is now CA $679 per person
CA $679
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (347 reviews)
Pool area was great

Reviewed on Sep 4, 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 $121 per night from Oct 6 to Oct 7
CA $121
CA $136 total
Oct 6 - Oct 7
includes taxes & fees
Quality Inn & Suites Orland Park - Chicago
Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr, Westmont, IL
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Oct 9 to Oct 10
CA $106
CA $117 total
Oct 9 - Oct 10
includes taxes & fees
Chicago Club Inn & Suites
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 $170 per night from Sep 21 to Sep 22
CA $170
CA $195 total
Sep 21 - Sep 22
includes taxes & fees
Hilton Chicago/Oak Lawn
See all 980 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $550. 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.