Orland Hills Vacations from ￥316,532

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The Latest Orland Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥435,978, price is now ￥316,532 per person
￥316,532
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Understaffed but staff was nice. Tiny rooms.

Reviewed on Aug 23, 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was ￥485,550, price is now ￥331,810 per person
￥331,810
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,014 reviews)
Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!

Reviewed on Aug 18, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥616,874, price is now ￥443,960 per person
￥443,960
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on Aug 19, 2025

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥445,492, price is now ￥323,058 per person
￥323,058
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (3,059 reviews)
Loved the property, big size room and very cool decoration! Great location

Reviewed on Aug 22, 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
Price was ￥456,478, price is now ￥332,201 per person
￥332,201
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Staff was amazing!! Everything was so easy checking in and checking out. The stay was great! It was so nice having the pier to ourselves after hours.

Reviewed on Aug 20, 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 ￥13,739 per night from Sep 7 to Sep 8
￥13,739
￥15,384 total
Sep 7 - Sep 8
includes taxes & fees
7.2/10 Good! (1,009 reviews)
"Property was clean and things were in proper order."

Reviewed on Aug 18, 2025

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 ￥11,241 per night from Sep 21 to Sep 22
￥11,241
￥12,475 total
Sep 21 - Sep 22
includes taxes & fees
7/10 Good! (1,241 reviews)
"We have stayed here several times and it has been nice. The property needs maintenance such as regular grooming of the grass and shrubs."

Reviewed on Aug 17, 2025

Chicago Club Inn & Suites
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway, Willowbrook, IL
Fully refundableReserve now, pay when you stay
The price is ￥8,680 per night from Sep 1 to Sep 2
￥8,680
￥9,719 total
Sep 1 - Sep 2
includes taxes & fees
6.2/10 (1,003 reviews)
"Chilis Target"

Reviewed on Aug 16, 2025

Red Roof Inn PLUS+ Chicago - Willowbrook
See all 988 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.

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 ￥316,532. 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.