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 1,273 total
includes taxes & fees
13 Oct - 14 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 living room with a grey sofa, a blue bench, and a white door leading to another room.

3. 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)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is AED 540
AED 888 total
includes taxes & fees
25 Oct - 26 Oct
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A modern kitchen with dark wood cabinets, stainless steel appliances, a granite countertop, and a small island with stools.

4. 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.

5. 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 1,223
AED 2,385 total
includes taxes & fees
13 Oct - 14 Oct
3-bedroom house in lovely Matteson with cool AC breeze
A modern kitchen with a dining table, chairs, and a built-in microwave.

6. Renovated 2BR Near Joliet | King Bed, Parking + Patio | Sleeps 6

Renovated 2BR Near Joliet | King Bed, Parking + Patio | Sleeps 6
Crest Hill
The price is AED 433
AED 1,403 total
includes taxes & fees
13 Oct - 14 Oct
Renovated 2BR Near Joliet | King Bed, Parking + Patio | Sleeps 6
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 783
AED 1,722 total
includes taxes & fees
20 Oct - 21 Oct
Spacious 3br home near Chicago, fenced yard for pets
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is AED 486
AED 1,111 total
includes taxes & fees
9 Nov - 10 Nov
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
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.
The price is AED 1,072
AED 2,378 total
includes taxes & fees
13 Oct - 14 Oct
Modern Spacious 4BR Home Near Chicago • Sleeps 10 • Family & Pets Friendly
A dining room with a wooden table set for six, flanked by bookshelves, and a view into another room through a glass door.

10. 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 837
AED 1,923 total
includes taxes & fees
11 Nov - 12 Nov
Travelers Retreat/King Beds/Game Room/Play House
A backyard with a barbecue grill, a dining table with chairs, and a fire pit.

11. 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.
The price is AED 478
AED 1,130 total
includes taxes & fees
14 Oct - 15 Oct
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.

12. 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.
The price is AED 845
AED 2,343 total
includes taxes & fees
13 Oct - 14 Oct
4BR Tudor • Wooded Lot • 10 Min to Downtown
A modern living room with a sofa set, a coffee table, and a rug.

13. 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
14 Oct - 15 Oct
Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield
A sunroom with white walls, wooden flooring, two blue armchairs, a small table with books, and hanging plants.

14. 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*
A wooden interior hallway with a staircase, a wooden wardrobe, and a cabinet with glass doors.

15. 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.
River Park Paradise w/ Fire Pit & Chef's Kitchen
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

16. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
7.8 out of 10, Good, (34 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is AED 545
AED 1,110 total
includes taxes & fees
13 Oct - 14 Oct
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
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 766 total
includes taxes & fees
13 Oct - 14 Oct
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

18. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveler
The price is AED 661
AED 1,360 total
includes taxes & fees
13 Oct - 14 Oct
LUXE 3 BR, 2 BA + Hot Tub
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

19. Romantic Escape - Adult Playhouse with Exotic Dungeon

Romantic Escape - Adult Playhouse with Exotic Dungeon
South Holland
8.8 out of 10, Excellent, (13 reviews)
"enjoyed my stay cant wait to book again "
United States
Anonymous traveler
The price is AED 1,432
AED 1,745 total
includes taxes & fees
19 Oct - 20 Oct
Romantic Escape - Adult Playhouse with Exotic Dungeon
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

20. PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.6 out of 10, Exceptional, (24 reviews)
"Great place Great location "
United States
Josh W.
The price is AED 879
AED 1,892 total
includes taxes & fees
13 Oct - 14 Oct
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
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

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

8/10 Good
"Great location to explore downtown chicago, and ideal for marathon runners. Kitchenette was a bit limited. Staff very friendly and helpful."
Laura 3-night trip
Posted less than an hour ago
Club Quarters Hotel, Central Loop, Chicago

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