Orland Park Holiday Rentals

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Check prices for these dates

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Orland Park holiday rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1027)
"My favorite place to stay hands-down"
United States
Michele
The price is HK$852
HK$1,229 total
includes taxes & fees
7 Jan - 8 Jan 2026
Sentral Michigan Avenue
Business centre
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Front of property
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is HK$1,023
HK$1,201 total
includes taxes & fees
5 Jan - 6 Jan 2026
Chicago luxury home suites
Exterior
River West, Second Floor Chicago by 747 Lofts

River West, Second Floor Chicago by 747 Lofts

River West, Second Floor Chicago by 747 Lofts
2.0 star property
West Town
9.6 out of 10, Exceptional, (4)
"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."
United States
Anonymous traveller
The price is HK$587
HK$2,699 total
includes taxes & fees
1 Jan - 2 Jan 2026
River West, Second Floor Chicago by 747 Lofts
Desk, laptop workspace, blackout curtains, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
Harvey
4.0 out of 10, (68)
"Good "
United States
Abel
The price is HK$592
HK$669 total
includes taxes & fees
1 Jan - 2 Jan 2026
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is HK$1,206
HK$3,185 total
includes taxes & fees
31 Jan - 1 Feb 2026
Classic Forest Park Foursquare < 1 Mi to Blue Line
Terrace/patio
Modern 4 Bedroom Private Vacation Home

Modern 4 Bedroom Private Vacation Home

Modern 4 Bedroom Private Vacation Home
2.5 star property
Shorewood
The price is HK$3,848
HK$4,852 total
includes taxes & fees
1 Jan - 2 Jan 2026
Modern 4 Bedroom Private Vacation Home
Private kitchen
River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (17)
"Loved the space and location "
United States
Caroline
The price is HK$686
HK$1,846 total
includes taxes & fees
2 Jan - 3 Jan 2026
River West, Third Floor Chicago by 747 Lofts
Private kitchen
Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts
2.0 star property
West Town
8.8 out of 10, Excellent, (13)
"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."
United States
Barbara
The price is HK$569
HK$1,644 total
includes taxes & fees
12 Jan - 13 Jan 2026
Chicago Second Floor Studio by 747 Lofts
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.
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Top Orland Park Hotel Reviews

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

10/10 Excellent
"Everything was excellent."
Jose 3-night trip
Posted 1 day ago
Silversmith Hotel Chicago Downtown

Find out more about Orland Park

Search for holiday rentals in Orland Park on Expedia! You can easily find your home rentals, villas, holiday apartments in Orland Park using one of the methods below:

  • View our selection of featured holiday rentals in Orland Park
  • Use the map to find apartments and other holiday homes in the Orland Park neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Orland Park while they last

Look no further and take a look at our great range of rental properties in Orland Park!

Frequently asked questions

Are there holiday rentals in Orland Park?

Yes, there are holiday rentals in Orland Park close to Orland Park Sportsplex, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Orland Park. Make sure you have time to check out the hockey games while you're in the area.

What are some of the best holiday rentals that Orland Park has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Orland Park offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What’s there to see and do in Orland Park?

Family-friendly attractions include Orland Park Sportsplex and Space Golf, whereas Centennial Park is a spot to enjoy the outdoors. Orland Square and Centennial Park Aquatic Center are other places to visit while you're in town.

What are holiday rentals like in Orland Park?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Orland Park. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family gatherings.