Orland Park Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Orland Park holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,118 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is HK$926
HK$1,317 total
includes taxes & fees
2 Apr - 3 Apr
Sentral Michigan Avenue
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (187 reviews)
"Nice area if you are renting a car, be aware that you would have to pay for street parking or go over a few blocks and park in a parking lot."
United States
Daysha
The price is HK$1,122
HK$1,961 total
includes taxes & fees
15 Apr - 16 Apr
Kasa River North Chicago
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is HK$1,254
HK$3,580 total
includes taxes & fees
14 Apr - 15 Apr
River North Rooftop With In and Out Parking 3
TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is HK$885
HK$1,779 total
includes taxes & fees
9 Apr - 10 Apr
Sunlit 1BR Apartment | Warm & Welcoming Space
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.4 out of 10, Exceptional, (16 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$541
HK$1,376 total
includes taxes & fees
12 Apr - 13 Apr
Modern Comfort: 1BR Unit w/ Laundry
1 bedroom, iron/ironing board, travel cot, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Great communication and hosts. Location and unit was perfect."
United States
Greg C.
The price is HK$886
HK$1,809 total
includes taxes & fees
2 Apr - 3 Apr
West Loop Living – Bright 1BR
TV, offices

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
The price is HK$886
HK$1,819 total
includes taxes & fees
2 Apr - 3 Apr
Chicago-Themed 1BR in a Central Spot near Downtown
Dining

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
The price is HK$807
HK$1,141 total
includes taxes & fees
14 Apr - 15 Apr
LIVN Millennium Park Downtown Chicago Studio
TV, offices

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (17 reviews)
"Great place"
United States
Daniel L.
The price is HK$1,756
HK$5,138 total
includes taxes & fees
19 Apr - 20 Apr
Modern West Loop Gem-City Views & Prime Location 6
1 bedroom, iron/ironing board, travel cot, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
The price is HK$1,066
HK$1,444 total
includes taxes & fees
9 Apr - 10 Apr
LIVN West Loop Chicago Queen Superior Studio
Exterior

Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (21 reviews)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
United States
Susan
The price is HK$555
HK$1,638 total
includes taxes & fees
3 Apr - 4 Apr
Ground Floor Studios in Chicago by 747 Lofts
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.0 out of 10, Very good, (2 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$886
HK$1,819 total
includes taxes & fees
5 Apr - 6 Apr
1BR Modern Luxe Apt with In-Unit Laundry
Interior

Spacious, lovely 2bed 1bath with free parking

Spacious, lovely 2bed 1bath with free parking
Oak Park
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place and neighborhood."
United States
Charles R.
The price is HK$1,235
HK$2,858 total
includes taxes & fees
3 Apr - 4 Apr
Spacious, lovely 2bed 1bath with free parking
Interior

Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Blue Island
7.6 out of 10, Good, (4 reviews)
"Only issue was the water pressure in the bathroom was very very low. "
United States
Derrick M.
The price is HK$1,157
HK$2,672 total
includes taxes & fees
2 Apr - 3 Apr
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Dining

LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Prem Studio
Downtown Chicago
The price is HK$807
HK$1,141 total
includes taxes & fees
14 Apr - 15 Apr
LIVN Millennium Park Downtown Chicago Prem Studio
TV

LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Superior 1BR
Downtown Chicago
LIVN Millennium Park Downtown Chicago Superior 1BR
Interior

Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
Downtown Chicago
The price is HK$996
HK$2,103 total
includes taxes & fees
13 Apr - 14 Apr
Stylish Japanese-Themed 2BR Apt Close to Downtown
Living area

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
LIVN Millennium Park Downtown Chicago 2BR
TV

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
LIVN Millennium Park Downtown Chicago Superior 2 BR
Living area

LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
LIVN Millennium Park Downtown Chicago 1 BR
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Orland Park Hotel Reviews

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

6/10 Okay
"If you need a great location and basic room for a great price then this is the hotel for you. If you have kids who want to swim and want a decent size room for your family then I’d recommend continuing your search elsewhere. The pool is VERY VERY small, don’t let the photos fool you. With 10-15 people swimming it was completely unenjoyable as you couldn’t move around. Towels were restocked often but they kept running out. The room had a good view but as a family of four I wish I would have explored other options as the room was dated and very small. Bathrooms not updated anytime recently but great water pressure! All in all if you need a quick stay as a party of 2 who don’t care to swim this is a great option with its location! But if you have kids who want to swim this place is not it!!"
Amanda K 2-night trip
Posted 1 hour ago
Hilton Garden Inn Chicago Downtown/Magnificent Mile

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?

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony: This holiday home rental outside of Orland Park is located in the city centre, and has a balcony, an arcade/games room and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Orland Park?

Expedia has 3 holiday rentals for your stay in Orland Park.

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.