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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 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 1,269 total
includes taxes & fees
20 Oct - 21 Oct
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A modern kitchen with dark wood cabinets, stainless steel appliances, a granite countertop, and a small island with stools.

2. 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 661
AED 1,707 total
includes taxes & fees
21 Oct - 22 Oct
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
A modern living room with a grey sofa, a black coffee table, and a large window with a view of a house and greenery.

3. 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
25 Oct - 26 Oct
Entire home in Lockport, Illinois
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 984
AED 2,075 total
includes taxes & fees
20 Oct - 21 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)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is AED 624
AED 989 total
includes taxes & fees
9 Nov - 10 Nov
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 393
AED 1,020 total
includes taxes & fees
20 Oct - 21 Oct
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 764
AED 1,697 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, (2 reviews)
"Great place to stay"
United States
Ken B.
The price is AED 746
AED 1,814 total
includes taxes & fees
25 Oct - 26 Oct
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, (4 reviews)
"Clean, Family friendly yes"
United States
ronald M.
The price is AED 897
AED 2,169 total
includes taxes & fees
26 Oct - 27 Oct
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)
"This property was perfect for our weekend stay in the Chicagoland area. It was conveniently located to activities, shops and restaurants. Vic is a wonderfully attentive host who responds quickly and is happy to answer any questions or concerns."
United States
Christine M.
The price is AED 471
AED 1,114 total
includes taxes & fees
20 Oct - 21 Oct
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
A modern kitchen with dark cabinets, stainless steel appliances, and a patterned tile backsplash.

11. 5-minute walk to the largest old school arcade in America! Family friendly.

5-minute walk to the largest old school arcade in America! Family friendly.
Brookfield
8.6 out of 10, Excellent, (9 reviews)
"A nice house that easily slept 4 kids and 4 adults. There were ants in the house, then than that it was very nice, it was easy to get to the train into Chicago from here."
United States
Ryan S.
The price is AED 754
AED 1,922 total
includes taxes & fees
20 Oct - 21 Oct
5-minute walk to the largest old school arcade in America! Family friendly.
A living room with a gray sofa, a blue chair, a fireplace, and a ceiling fan.

12. 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.
PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!
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 1,745 total
includes taxes & fees
20 Oct - 21 Oct
Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield
A spacious living room with a fireplace, a large sofa, a coffee table, and a TV.

14. 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 735
AED 2,195 total
includes taxes & fees
21 Oct - 22 Oct
4BR Tudor • Wooded Lot • 10 Min to Downtown
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)
"Great house that worked out perfectly for our group."
United States
Rich D.
The price is AED 845
AED 1,677 total
includes taxes & fees
15 Nov - 16 Nov
The Heron House, King Bed Suite, *Spacious Remodeled House*
A building with a sign reading 'Hale Street Cantina' and a brick facade.

16. ✽ 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
20 Oct - 21 Oct
✽ Charming Cottage ✽ close to College/Town/Station
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, (36 reviews)
"I had a fun stay "
United States
Jusu K.
The price is AED 526
AED 766 total
includes taxes & fees
21 Oct - 22 Oct
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
(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.

18. 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.
30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious
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 1,425 total
includes taxes & fees
20 Oct - 21 Oct
Lombard 1BR & 1BH Suite Close to freeway & Mall
A bedroom with a bed, bedside tables, a dresser, a mirror, and a hanging light fixture.

20. Spacious 7-bedroom house with AC in wonderful Naperville

Spacious 7-bedroom house with AC in wonderful Naperville
Naperville
8.0 out of 10, Very good, (1 review)
"Very smooth booking, checking in, and checking out process. The house was older, and it showed, but was big enough to hold my group. There were problems with the fire detectors randomly beeping, and some mold in the basement, but everything else was fine."
United States
Brett H.
The price is AED 1,719
AED 3,994 total
includes taxes & fees
20 Oct - 21 Oct
Spacious 7-bedroom house with AC in wonderful Naperville
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

River Hotel

River Hotel

10/10 Excellent
"The room size was big enough for me. I had a good view of the river and downtown. The staff was helpful. There was no restaurant in the building, but it was one on each side of the hotel."
Isaac Lee 3-night trip
Posted 1 hour ago
River Hotel

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