Orland Hills Holidays from NZ$2,859

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Top Holiday Package Deals in Orland Hills

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was NZ$3,702, price is now NZ$2,859 per person
NZ$2,859
per person
30 Oct - 4 Nov
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (347 reviews)
Pool area was great

Reviewed on 4 Sept 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was NZ$5,454, price is now NZ$3,814 per person
NZ$3,814
per person
30 Oct - 4 Nov
found 1 day ago
Return direct flight included
Auckland (AKL) 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 8 Sept 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was NZ$4,112, price is now NZ$3,090 per person
NZ$3,090
per person
30 Oct - 4 Nov
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
The rooms were not very well decorated. The furniture used in the room looks like furniture from a detention house. Not my favorite.

Reviewed on 8 Sept 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$4,061, price is now NZ$3,181 per person
NZ$3,181
per person
30 Oct - 4 Nov
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
The property is gorgeous! Lovely rooms and the staff were fantastic, could not fault them at all! My only issue would be the roads outside are very noisy, we needed ear plugs to sleep. Other than that, absolutely fantastic stay! Would return and would highly recommend

Reviewed on 8 Sept 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was NZ$7,281, price is now NZ$5,782 per person
NZ$5,782
per person
30 Oct - 4 Nov
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.8/10 Exceptional! (1,014 reviews)
Amazing hotel will be back for sure!

Reviewed on 7 Sept 2025

Our pick of the best 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 NZ$166 per night from 6 Oct to 7 Oct
NZ$166
6 Oct - 7 Oct
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 NZ$127 per night from 9 Oct to 10 Oct
NZ$127
9 Oct - 10 Oct
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 NZ$239 per night from 17 Sept to 18 Sept
NZ$239
17 Sept - 18 Sept
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.

Frequently asked questions

How much does an Orland Hills holiday package cost?
Browse and book everything in one place with our Orland Hills holiday packages, which start from just NZ$2,859. 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 holiday 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 holiday?
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 holiday!
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 holiday package lets you organise your escape your way. Plus, you'll score great discounts when you combine your accommodation 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 holiday package?
With a holiday 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 holiday package?
Whether it's your hotel or flight, you can cancel and rebook it. Booked your Orland Hills holiday 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.