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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Amazing amenities. friendly staff and clean rooms. Views from the balcony were so nice!

Reviewed on Jul. 12, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 hour ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I love Virgin air and expected a 5-star experience. Hotel checkin was not all that welcoming, but efficientl. They had no valet service and basically told us we were on our own. Thought ok I need a drink so went to the rooftop bar. An afterthought at this hotel. Cushions were dirty and faded. Barely staffed. More like a rooftop bar in costs rica than downtown Chicago. Room was nice and stylish. The highlight of the stay tbh as was the coffee shop.

Reviewed on Jul. 13, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 hour ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Amazing customer service

Reviewed on Jul. 13, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 hour ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
The availability to get water without being charge $4 or more was impossible. Water from the tap is essential but Chicago hard water does not make it drinkable water. The hotel charging for drinkable water in the heat of summer was a really bad image when everything else was certainly great.

Reviewed on Jul. 13, 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 $126 per night from Aug 10 to Aug 11
CA $126
CA $141 total
Aug 10 - Aug 11
includes taxes & fees
7.2/10 Good! (1,005 reviews)
"Room was spacious and the kitchen was nice. It could have been cleaned a little better. We found a fake fingernail on the floor. Overall would stay again if it was cheaper."

Reviewed on Jul. 7, 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 $152 per night from Jul 20 to Jul 21
CA $152
CA $171 total
Jul 20 - Jul 21
includes taxes & fees
7.8/10 Good! (1,022 reviews)
"So convenient for all and to my needs! So convenient for my family visit!"

Reviewed on Jul. 11, 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
The price is CA $185 per night from Jul 27 to Jul 28
CA $185
CA $205 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Stay was great"

Reviewed on Jul. 12, 2025

The Westin Chicago Lombard
See all 937 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 $688. 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.