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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 Oak Lawn 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 826
AED 1,171 total
includes taxes & fees
14 Oct - 15 Oct
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

2. 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
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.

3. 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 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 wooden deck with a railing, a staircase, and a window with a wreath.

5. 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 living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

6. 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
14 Oct - 15 Oct
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

7. 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 818
AED 1,747 total
includes taxes & fees
14 Oct - 15 Oct
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
A modern kitchen with stainless steel appliances, a marble countertop, and grey cabinetry.

8. 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 1,012
AED 2,306 total
includes taxes & fees
14 Oct - 15 Oct
Modern Spacious 4BR Home Near Chicago • Sleeps 10 • Family & Pets Friendly
A modern living room with a grey sofa, a black coffee table, and a large window with a view of a house and greenery.

9. 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 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.

10. 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
14 Oct - 15 Oct
3-bedroom house in lovely Matteson with cool AC breeze
A modern living room with a sectional sofa, a coffee table, and a TV.

11. Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
8.6 out of 10, Excellent, (4 reviews)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
The price is AED 661
AED 862 total
includes taxes & fees
19 Oct - 20 Oct
Attractive Coach House Apartment for rent in Oak Park.
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

12. 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 backyard with a barbecue grill, a dining table with chairs, and a fire pit.

13. 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 living room with a brown sofa, a coffee table, and a patterned rug. There is a staircase leading to another room.

14. 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 modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

15. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room
Brookfield
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful place to stay!"
United States
Chasity D.
The price is AED 908
AED 2,706 total
includes taxes & fees
2 Nov - 3 Nov
Vibrant House, Walk to Train, Game Room
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

16. 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 1,308 total
includes taxes & fees
14 Oct - 15 Oct
LUXE 3 BR, 2 BA + Hot Tub
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

17. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is AED 376
AED 2,135 total
includes taxes & fees
15 Oct - 16 Oct
Theater • Game Room • Gym • Firepit • 4BR Home
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

18. Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded promptly and was accommodating. Would book and recommend to others!"
United States
Ashley Y.
The price is AED 910
AED 3,921 total
includes taxes & fees
22 Oct - 23 Oct
Sleeps 18 • 8BR • Game Room • Gym • Theater
Room

19. Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
9.0 out of 10, Wonderful, (4 reviews)
"Good place for a large group or family."
United States
Daniel J.
The price is AED 617
AED 2,972 total
includes taxes & fees
14 Oct - 15 Oct
Arcade • Theater • Gym • Office • Sleeps 15
A single-story house with a covered porch, a front door, and a small garden area.

20. Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (4 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is AED 721
AED 1,292 total
includes taxes & fees
29 Oct - 30 Oct
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
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 Oak Lawn Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"A great visit and Ken at the front desk was a wonderful help through our entire stay!"
isabelle 3-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast

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