Orland Park Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Orland Park vacation rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1025)
"My favorite place to stay hands-down"
United States
Michele
The price is ￥18,500
￥26,311 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sentral Michigan Avenue
Business center
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
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is ￥9,837
￥26,307 total
includes taxes & fees
Jan 27 - Jan 28, 2026
1BR Modern Luxe Apt with In-Unit Laundry
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Stylish 1BR in West Loop

Stylish 1BR in West Loop
Downtown Chicago
10.0 out of 10, Exceptional, (10)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is ￥9,837
￥26,307 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
The price is ￥9,837
￥26,307 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Sleek 1BR Apt w/ Laundry
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (5)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is ￥9,837
￥26,307 total
includes taxes & fees
Jan 27 - Jan 28, 2026
West Loop Living – Bright 1BR
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"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 ￥9,837
￥26,307 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very Good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is ￥9,864
￥26,379 total
includes taxes & fees
Jan 7 - Jan 8, 2026
The One: A 1BR Stay That Feels Like Home
Front of property
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (5)
"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 ￥16,486
￥19,355 total
includes taxes & fees
Dec 29 - Dec 30
Chicago luxury home suites
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.8 out of 10, Exceptional, (16)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is ￥10,774
￥29,747 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Twice as Nice: Chic 2BR Stay with Style & Space
Iron/ironing board, travel crib, WiFi, bed sheets
Modern Studio Near UChicago

Modern Studio Near UChicago

Modern Studio Near UChicago
Hyde Park
9.6 out of 10, Exceptional, (11)
"Clean room and convenient location! "
United States
Gabriela
The price is ￥8,924
￥23,712 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Modern Studio Near UChicago
Interior
Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt
Hyde Park
9.6 out of 10, Exceptional, (4)
"Nice place for a girls trip weekend. "
United States
Madonna A.
The price is ￥9,081
￥27,810 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Sleek & Functional 2-Bedroom Apt
Studio | Exterior
Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (6)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
The price is ￥9,751
￥34,870 total
includes taxes & fees
Dec 30 - Dec 31
Chicago Third Floor Studio by 747 Lofts
Private kitchen
Spacious 3-bedroom apartment near downtown, FREE PARKING

Spacious 3-bedroom apartment near downtown, FREE PARKING

Spacious 3-bedroom apartment near downtown, FREE PARKING
Near West Side
9.4 out of 10, Exceptional, (10)
"Nice place to stay. Good communication with the owner."
United States
Ryan
The price is ￥9,056
￥50,285 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Spacious 3-bedroom apartment near downtown, FREE PARKING
Fridge, microwave, oven, stovetop
Explore Hyde Park: 2BR Apt on Blackstone Ave

Explore Hyde Park: 2BR Apt on Blackstone Ave

Explore Hyde Park: 2BR Apt on Blackstone Ave
Hyde Park
8.4 out of 10, Very Good, (5)
"Host was responsive to my questions. Apartment is located in a great area of Hyde Park. "
United States
Lind A.
The price is ￥9,394
￥28,176 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Explore Hyde Park: 2BR Apt on Blackstone Ave
Fridge, microwave, oven, stovetop
Flexhome Ukrainian Village 2BR D1

Flexhome Ukrainian Village 2BR D1

Flexhome Ukrainian Village 2BR D1
West Town
9.6 out of 10, Exceptional, (5)
"It was clean and ready for our arrival. A big plus is having a washer and dryer on the premises."
United States
Ray R.
The price is ￥9,723
￥25,522 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Flexhome Ukrainian Village 2BR D1
Fridge, microwave, oven, stovetop
Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Lawndale
10.0 out of 10, Exceptional, (8)
"Very nice apartment close to downtown!"
United States
Dariana
The price is ￥8,924
￥31,069 total
includes taxes & fees
Dec 29 - Dec 30
Cozy Boho Chicago - 10 Minutes to Downtown Chicago
3 bedrooms, iron/ironing board, WiFi, bed sheets
Furnished 3BR Apt w/ Laundry

Furnished 3BR Apt w/ Laundry

Furnished 3BR Apt w/ Laundry
Hyde Park
9.6 out of 10, Exceptional, (4)
"Apartment and neighborhood were beautiful. We really enjoyed our stay and would book the same place again!"
United States
Kristin W.
The price is ￥11,711
￥33,382 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Furnished 3BR Apt w/ Laundry
Iron/ironing board, travel crib, WiFi, bed sheets
Studio Unit | Chic + Prime Location

Studio Unit | Chic + Prime Location

Studio Unit | Chic + Prime Location
Hyde Park
10.0 out of 10, Exceptional, (2)
"Location was just perfect!"
United States
Meg D.
The price is ￥8,924
￥23,712 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Studio Unit | Chic + Prime Location
TV, offices
Complete 1BR Home Sum

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is ￥9,837
￥26,307 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Complete 1BR Home Sum
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

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

10/10 Excellent
"It was a very clean room, easy check in and out, lovely staff that helped me retrieve my lost item very effectively. Overall a very lovely experience. "
Paxton 2-night trip
Posted 1 day ago
DoubleTree by Hilton Chicago - 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
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  • 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 vacation rentals in Orland Park?

Yes, there are vacation rentals in Orland Park near Orland Park Sportsplex, or you can choose a secluded option if you're looking for extra privacy while you relax. 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's the top vacation rental that Orland Park has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: Visitors like this Orland Park vacation home rental. It offers a patio, a barbecue grill, 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 vacation rentals like in Orland Park?

Vacation rentals are privately owned properties you can book for several days or more in Orland Park. Vacation rentals feature extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for small groups.