Orland Park Holidays from £885

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Your Orland Park Holiday

Get ready to experience Orland Park on your terms with a custom Orland Park holiday package! Discovering the treasures of this lively city is easy with a base in a neighbourhood such as Flossmoor, which is great for golfing, among lots of other things. Like to get out and explore? Orland Park Sportsplex, Orland Square and Centennial Park are just a few of the most popular places to visit during a trip to Orland Park. Stop dreaming and start doing. Browse the broad range of options on Expedia today and finally put your Orland Park holiday plans into gear!

Top Orland Park Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,084, price is now £885 per person
£885
per person
27 Dec - 31 Dec
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on 8 Nov 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,196, price is now £889 per person
£889
per person
1 Feb - 8 Feb
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,542, price is now £1,214 per person
£1,214
per person
27 Dec - 31 Dec
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was £1,857, price is now £1,512 per person
£1,512
per person
27 Dec - 31 Dec
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

The Glen Club

The Glen Club

4 out of 5
Price was £1,078, price is now £889 per person
£889
per person
1 Feb - 8 Feb
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (402 reviews)

Orland Park Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
58,600
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Odyssey Fun World, Hollywood Casino Amphitheatre and Centennial Park

Top hotels in Orland Park

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is £104 per night from 22 Nov to 23 Nov
£104
22 Nov - 23 Nov
includes taxes & fees
8/10 Very good! (10,074 reviews)
"The room was really nice and clean. The only thing that I was not to pleased with was the bed. It was super hard. That was only thing I was not satisfied with."

Reviewed on 13 Nov 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is £92 per night from 24 Nov to 25 Nov
£92
24 Nov - 25 Nov
includes taxes & fees
8.8/10 Excellent! (5,608 reviews)
"Room service was great, always nice and clean when I got back."

Reviewed on 13 Nov 2026

River Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £144 per night from 22 Nov to 23 Nov
£144
22 Nov - 23 Nov
includes taxes & fees
Hilton Chicago
See all 3,269 properties in Orland Park
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 Holidays
All Inclusive Holidays
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Beach Holidays
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Family Friendly Holidays

Stay near popular Orland Park attractions

Orland Square

8.4/10 (33 reviews)
Orland Square Mall offers over 130 stores and dining options in Chicago's southwest suburbs. Browse upscale retailers like Apple and Sephora, then indulge at The Cheesecake Factory or Texas de Brazil.
See properties

What to do in Orland Park

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Orland Park

Frequently asked questions

How much does an Orland Park travel package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Orland Park from just £885. And the more you bundle, the more you save. Your dream holiday has never been more affordable.
If I'm not able to travel, can I cancel my Orland Park travel package?
We totally get it — life doesn't always go according to plan. If you've locked in an Orland Park travel package and need to change or cancel it, we can help. It's always worth looking up our Customer Service Portal first for information. But generally, if you've taken out your package within 24 hours, you may be able to amend or cancel your itinerary at no cost. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.
How do I get a cheap travel package to Orland Park?
Crafting your own Orland Park travel package with Expedia is a great way to save. We offer access to over 550 airlines and 1,000,000 properties globally. With such an extensive range to choose from, you'll have no issues creating your next dream getaway.
Does Expedia offer Book Now, Pay Later Orland Park holidays?
Your bank balance shouldn't stop you from taking a holiday, so Expedia has worked out a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a fantastic getaway without exhausting your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's convenient monthly instalment plans. If paying a little each month sounds right for you, pick this option during the checkout process.
  • Pay in instalments holidays: Into the idea of paying for your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan from Klarna.

Where should I stay in Orland Park?
A holiday in Orland Park wouldn't be complete without paying a visit to Orland Park Sportsplex, Orland Square and Centennial Park. Stay close to these attractions and make sightseeing a breeze.
What are the top hotels in Orland Park?
Secure a room at Hyatt Regency Chicago. It's one of the area's most sought-after properties. Another reputable option in Orland Park is The Godfrey Hotel Chicago.
How far in advance should I book my Orland Park holiday?
The earlier, the better. Air carriers usually release flight tickets around a year ahead of departure, and this is an excellent opportunity to land some of the lowest prices. Just been told you should take all your holiday days next week? That's fine too — Expedia are never short on fantastic bargains to whisk you away on the getaway of your dreams, at a price you can afford.
What does an Expedia Orland Park travel package include?
It all comes down to what kind of getaway you're contemplating. Orland Park holiday deals can include flights, hotels and car rentals. You can mix and match to find the package that suits your budget and style. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking an Orland Park travel package?
You'll score great savings when you bundle your flights, hotels and rental cars into a travel package. Plus, booking everything together makes trip planning easier. So why waste your money or time? Whether you're putting together a fancy romantic getaway or a low-cost family road trip, check out our travel packages today.
Can I choose my airline with an Orland Park Expedia travel package?
You can, and with over 550 airlines to pick from worldwide, you're spoiled for choice. Browse the available options and find out which airline best suits your needs and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.