A calm lake at sunset with grassy banks and trees in the background.

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Orland Park vacation homes

A bedroom with a stone wall, a TV mounted on it, a bed with a white comforter, and a view of the outdoors through a window.

1. Beautifully furnished one bedroom loft located in Chicago's South side suburb

Beautifully furnished one bedroom loft located in Chicago's South side suburb
Hazel Green
10.0 out of 10, Exceptional, (1 review)
"Super great location, we had a concert at Tinley Park, then explored Chicago with a river cruise and Second City Everything was perfect and so eat to just chill, come and go as we pleased In a nice neighborhood and interior was furnished beautifully. Definitely worth the price !!"
United States
Nick L.
The price is AED 900
AED 1,261 total
includes taxes & fees
15 Oct - 16 Oct
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A modern living room with a grey sofa, a black coffee table, and a large window with a view of a house and greenery.

2. Entire home in Lockport, Illinois

Entire home in Lockport, Illinois
Lockport
8.8 out of 10, Excellent, (5 reviews)
"The house is very clean. The host was very kind and responsive. "
United States
Susan B.
The price is AED 718
AED 1,563 total
includes taxes & fees
15 Oct - 16 Oct
Entire home in Lockport, Illinois
A modern kitchen with dark wood cabinets, stainless steel appliances, a granite countertop, and a small island with stools.

3. Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Lockport
10.0 out of 10, Exceptional, (15 reviews)
"Perfect spot for our group of 6! More than enough dishes/silverware etc. the house was clean and comfortable. Would definitely stay again if in the area."
United States
Kathy L.
The price is AED 826
AED 1,906 total
includes taxes & fees
8 Nov - 9 Nov
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
A dining area with a black table set for four, surrounded by chairs. A vase with dried flowers and a candle holder are on the table.

4. 3-bedroom house in lovely Matteson with cool AC breeze

3-bedroom house in lovely Matteson with cool AC breeze
Matteson
10.0 out of 10, Exceptional, (1 review)
"clean, comfortable, hosts very responsive to communications, neighborhood felt safe, perfect location for our stay to attend sectionals NTRP tennis tournament at HF Racquet and Fitness Club"
United States
Susan H.
The price is AED 1,227
AED 2,373 total
includes taxes & fees
19 Oct - 20 Oct
3-bedroom house in lovely Matteson with cool AC breeze
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

5. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
9.4 out of 10, Exceptional, (3 reviews)
The price is AED 624
AED 989 total
includes taxes & fees
27 Oct - 28 Oct
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

6. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is AED 474
AED 1,094 total
includes taxes & fees
9 Nov - 10 Nov
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A living room with a brown sofa, a coffee table, and a patterned rug. There is a staircase leading to another room.

7. Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
Richton Park
9.0 out of 10, Wonderful, (30 reviews)
"Very spacious accommodations in a very nice neighborhood. Convenient to food and shopping. Great value for the cost. "
United States
Greg S.
The price is AED 774
AED 1,708 total
includes taxes & fees
20 Oct - 21 Oct
Spacious 3br home near Chicago, fenced yard for pets
A dining room with a wooden table set for six, flanked by bookshelves, and a view into another room through a glass door.

8. Travelers Retreat/King Beds/Game Room/Play House

Travelers Retreat/King Beds/Game Room/Play House
Joliet
10.0 out of 10, Exceptional, (1 review)
"Lots of space, clean, welcoming."
United States
MIke L.
The price is AED 834
AED 1,919 total
includes taxes & fees
10 Nov - 11 Nov
Travelers Retreat/King Beds/Game Room/Play House
A modern kitchen with stainless steel appliances, a marble countertop, and grey cabinetry.

9. Modern Spacious 4BR Home Near Chicago • Sleeps 10 • Family & Pets Friendly

Modern Spacious 4BR Home Near Chicago • Sleeps 10 • Family & Pets Friendly
Westmont
10.0 out of 10, Exceptional, (3 reviews)
"Clean, Family friendly yes"
United States
ronald M.
Modern Spacious 4BR Home Near Chicago • Sleeps 10 • Family & Pets Friendly
A backyard with a barbecue grill, a dining table with chairs, and a fire pit.

10. PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.4 out of 10, Exceptional, (36 reviews)
"Clean house, Nice amenities, roomy and Close to the city! We very much enjoyed our stay here. "
United States
Ella A.
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
A spacious living room with a fireplace, a large sofa, a coffee table, and a TV.

11. 4BR Tudor • Wooded Lot • 10 Min to Downtown

4BR Tudor • Wooded Lot • 10 Min to Downtown
Naperville
9.6 out of 10, Exceptional, (5 reviews)
"This is a spacious house in a very nice, quiet neighborhood. The backyard is a perfect spot to relax and soak in the sun/play games. This is a great house for families. We had a nearby wedding and this was a wonderful house to get ready at. The hosts are extremely welcoming and communicate wonderfully. "
United States
Alicia F.
4BR Tudor • Wooded Lot • 10 Min to Downtown
A modern living room with a sofa set, a coffee table, and a rug.

12. Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield

Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield
Plainfield
10.0 out of 10, Exceptional, (3 reviews)
"Great host and the home location is awesome for hosting family. "
United States
Yolanda P.
The price is AED 714
AED 1,734 total
includes taxes & fees
15 Oct - 16 Oct
Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield
A wooden interior hallway with a staircase, a wooden wardrobe, and a cabinet with glass doors.

13. River Park Paradise w/ Fire Pit & Chef's Kitchen

River Park Paradise w/ Fire Pit & Chef's Kitchen
Bolingbrook
10.0 out of 10, Exceptional, (15 reviews)
"Excellent just what we were looking for"
United States
Sue B.
The price is AED 1,671
AED 3,227 total
includes taxes & fees
15 Oct - 16 Oct
River Park Paradise w/ Fire Pit & Chef's Kitchen
A living room with a gray sofa, a blue chair, a fireplace, and a ceiling fan.

14. PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!

PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!
Aurora
9.2 out of 10, Wonderful, (15 reviews)
"The beds were super comfortable and the location for Naperville/Aurora/Wheaton activities was ideal--about 10 minutes or so for everything."
United States
Scott D.
The price is AED 640
AED 1,356 total
includes taxes & fees
19 Oct - 20 Oct
PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!
A sunroom with white walls, wooden flooring, two blue armchairs, a small table with books, and hanging plants.

15. The Heron House, King Bed Suite, *Spacious Remodeled House*

The Heron House, King Bed Suite, *Spacious Remodeled House*
Joliet
10.0 out of 10, Exceptional, (55 reviews)
"This is a very clean and well appointed house with good parking. The owner was responsive to our requests"
United States
Nancy H.
The price is AED 882
AED 1,727 total
includes taxes & fees
9 Nov - 10 Nov
The Heron House, King Bed Suite, *Spacious Remodeled House*
(OUTDOOR SPACE) Where comfort and charm come together. Unwind in the outdoor lounge set under an inviting gazebo with twinkling lights. Stay fresh with a gentle breeze from the fan as you relax.

16. 30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious

30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious
Plainfield
9.4 out of 10, Exceptional, (18 reviews)
"Great place to stay."
United States
Taylor E.
The price is AED 1,080
AED 2,717 total
includes taxes & fees
18 Oct - 19 Oct
30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious
A wooden deck with a railing, a staircase, and a window with a wreath.

17. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (35 reviews)
"I had a fun stay "
United States
Jusu K.
The price is AED 526
AED 757 total
includes taxes & fees
18 Oct - 19 Oct
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A building with a sign reading 'Hale Street Cantina' and a brick facade.

18. ✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (74 reviews)
"This was the perfect place for our short stay!"
United States
Laurie R.
The price is AED 661
AED 1,179 total
includes taxes & fees
19 Oct - 20 Oct
✽ Charming Cottage ✽ close to College/Town/Station
A two-story house with a garage, solar panels, and a red car parked in front.

19. Lombard 1BR & 1BH Suite Close to freeway & Mall

Lombard 1BR & 1BH Suite Close to freeway & Mall
Lombard
The price is AED 456
AED 1,414 total
includes taxes & fees
19 Oct - 20 Oct
Lombard 1BR & 1BH Suite Close to freeway & Mall
A living room with a large window, a sofa, a chair, and a desk with a vase of flowers.

20. Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong

Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
Naperville
The price is AED 604
AED 1,831 total
includes taxes & fees
15 Oct - 16 Oct
Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
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

Hyatt Regency Chicago

Hyatt Regency Chicago

8/10 Good
"The hotel was beautiful, great location"
Addison 3-night trip
Posted less than an hour ago
Hyatt Regency Chicago

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