Orland Park Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Orland Park

Business center
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (176)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (981)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is ￥19,192
￥27,033 total
includes taxes & fees
Dec 9 - Dec 10
Sentral Michigan Avenue
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

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

Downtown Chicago
9.6 out of 10, Exceptional, (13)
"Had a very nice time in Chicago!"
United States
Valerie S.
The price is ￥14,953
￥34,804 total
includes taxes & fees
Nov 12 - Nov 13
Twice as Nice: Chic 2BR Stay with Style & Space
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 5

Downtown Chicago
10.0 out of 10, Exceptional, (2)
"As advertised. Beautiful, well appointed apartment. Centrally located to restaurants, shopping and the L train. Hosts were very communicative and attentive to our needs. Highly recommend. "
United States
Mike S.
The price is ￥17,573
￥49,975 total
includes taxes & fees
Dec 11 - Dec 12
River North Rooftop With In and Out Parking 5
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Stylish 1BR in West Loop

Downtown Chicago
10.0 out of 10, Exceptional, (9)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is ￥11,099
￥27,596 total
includes taxes & fees
Nov 12 - Nov 13
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1

Downtown Chicago
9.0 out of 10, Wonderful, (2)
"Clean rooms Adequate kitchen space Dishwasher Fast wifi with desk area to work. Near to many restaurants. Area felt safe. Communication with hosts was excellent. Minor misunderstandings resolved efficiently and completely. Beds are firm. Shower head was a little odd, almost like a strong mist and couldn't turn the showerhead to change the output. Not a real issue for me with little hair, but if you were a woman with long, thick hair, I could see it potentially being an issue. Upstairs...
United States
Ryan M.
The price is ￥15,415
￥47,851 total
includes taxes & fees
Nov 19 - Nov 20
River North Rooftop With In and Out Parking 1
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home

Downtown Chicago
9.4 out of 10, Exceptional, (3)
"Convenient location and clean place"
United States
David S.
The price is ￥11,099
￥27,596 total
includes taxes & fees
Nov 17 - Nov 18
The One: A 1BR Stay That Feels Like Home
1 bedroom, WiFi, bed sheets
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 ￥11,099
￥27,596 total
includes taxes & fees
Nov 12 - Nov 13
1BR Modern Luxe Apt with In-Unit Laundry
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

West Loop Living – Bright 1BR

Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Thorough and easy to follow parking and check in instructions. Clean apartment. "
United States
Kira V.
The price is ￥11,099
￥27,596 total
includes taxes & fees
Nov 13 - Nov 14
West Loop Living – Bright 1BR
Fridge, microwave, oven, stovetop
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 ￥11,099
￥27,596 total
includes taxes & fees
Nov 13 - Nov 14
Sun-Drenched 1BR Apartment
2 bedrooms, desk, iron/ironing board, free WiFi
Your Chicago get Away

Your Chicago get Away

Downtown Chicago
8.4 out of 10, Very Good, (8)
"We came to Chicago to visit museums and the apartment was clean and conveniently located. It had everything we needed for our stay. One note, parking is listed as an amenity. However, it wasn’t included, though there were many secure lots within a block to pay and park."
United States
Laura D.
Your Chicago get Away
2 bedrooms, desk, WiFi, bed sheets
South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3

Downtown Chicago
8.0 out of 10, Very Good, (3)
"Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. "
Australia
Angela M.
The price is ￥18,652
￥51,418 total
includes taxes & fees
Nov 24 - Nov 25
South Loop Rooftop With In and Out Parking 3
Fridge, microwave, oven, stovetop
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 ￥11,099
￥27,789 total
includes taxes & fees
Nov 19 - Nov 20
Sleek 1BR Apt w/ Laundry
Private kitchen
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, (8)
"Nice place to stay. Good communication with the owner."
United States
Ryan
The price is ￥9,866
￥53,070 total
includes taxes & fees
Nov 19 - Nov 20
Spacious 3-bedroom apartment near downtown, FREE PARKING
Interior
River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3

Downtown Chicago
9.4 out of 10, Exceptional, (3)
"really nice place in a great location. Pretty effortless check in a and check out. It does seem you have to pay for the parking, which would have factored into my decision to choose this spot (38). I thought it was included but as we left, we were forced to pay to leave the parking lot. Also, parking is in a nearby building but really not far at all."
United States
David S.
The price is ￥22,198
￥56,099 total
includes taxes & fees
Nov 24 - Nov 25
River North Rooftop With In and Out Parking 3
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6

Downtown Chicago
8.0 out of 10, Very Good, (1)
"Location was extremely ideal. Staff very responsive. All the apartments were very clean. The pictures were very accurate to what you can expect"
Canada
john Z.
The price is ￥21,427
￥55,016 total
includes taxes & fees
Nov 16 - Nov 17
River North Rooftop With In and Out Parking 6
Terrace/patio
River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
The price is ￥22,968
￥56,992 total
includes taxes & fees
Dec 4 - Dec 5
River North Private Balcony With In and Out Parking
Exterior
A quiet stay while you are away

A quiet stay while you are away

Oak Park
9.8 out of 10, Exceptional, (32)
"We picked Jay's house because it's located right in the middle of Oak Park where many of Frank Lloyd Wright's works are located, we had so much fun walking the beautiful neighborhood. Jay's property is great too!"
United States
Yimei Z.
The price is ￥8,970
￥29,682 total
includes taxes & fees
Nov 24 - Nov 25
A quiet stay while you are away
Studio | Exterior
Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts

2.0 star property
West Town
9.6 out of 10, Exceptional, (5)
"Excellent facility with great amenities: laundry, kitchen and a great location close to the Loop and easy access to O’Hare airport via Blue Line or Kennedy Expressway."
United States
Philip
The price is ￥8,978
￥33,497 total
includes taxes & fees
Nov 13 - Nov 14
Chicago Third Floor Studio by 747 Lofts
Microwave, oven, stovetop
Pleasant 3-bedroom house in Sauk Village

Pleasant 3-bedroom house in Sauk Village

2.0 star property
Sauk Village
10.0 out of 10, Exceptional, (1)
"My Experience Was (NOTHING) Short Of Perfect! The Place Is Nice & The Host Was Even Better! I’ll Forsure Be Booking Again! "
United States
Aaron K.
The price is ￥12,274
￥20,517 total
includes taxes & fees
Nov 23 - Nov 24
Pleasant 3-bedroom house in Sauk Village
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

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Friendly staff, very comfortable room"
Randall 2-night trip
Posted 9 hours ago
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Find out more about Orland Park

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Frequently asked questions

Are there vacation rentals in Orland Park?

Yes, there are vacation rentals in Orland Park near Centennial Park Aquatic Center, 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 Centennial Park Aquatic Center and Orland Park Sportsplex, whereas Centennial Park is a spot to enjoy the outdoors. Orland Square and Space Golf 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.