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Check prices for these dates

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

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.
$322 nightly
The price is $344
Oct 18 - Oct 19
Total with taxes and fees
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.
$254 nightly
The price is $269
Nov 9 - Nov 10
Total with taxes and fees
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A modern living room with a sofa, coffee table, TV, and a staircase leading to an upper floor.

3. Spacious 5BR 2BA Berwyn Home

Spacious 5BR 2BA Berwyn Home
Berwyn
10.0 out of 10, Exceptional, (1 review)
"experience was good i loved it honestly "
United States
jamya w.
$565 nightly
The price is $603
Oct 22 - Oct 23
Total with taxes and fees
Spacious 5BR 2BA Berwyn Home
A wooden deck with a railing, a staircase, and a window with a wreath.

4. 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)
"Highly recommend this property. It’s located on a quiet clean nice residential street. And the home itself is wonderful: good furnishings, comfortable, three good bedrooms, clean well appointed bathroom, great backyard. I’d stay here anytime I’m in the area."
United States
Ruth Ann G.
$186 nightly
The price is $208
Oct 19 - Oct 20
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
$285 nightly
The price is $302
Oct 21 - Oct 22
Total with taxes and fees
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.

6. 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.
$502 nightly
The price is $519
Oct 20 - Oct 21
Total with taxes and fees
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

7. 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
$667 nightly
The price is $811
Oct 26 - Oct 27
Total with taxes and fees
Theater • Game Room • Gym • Firepit • 4BR Home
A modern living room with a sectional sofa, a coffee table, and a TV.

8. 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.
$205 nightly
The price is $235
Oct 21 - Oct 22
Total with taxes and fees
Attractive Coach House Apartment for rent in Oak Park.
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

9. 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.
$478 nightly
The price is $512
Oct 20 - Oct 21
Total with taxes and fees
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
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.
$561 nightly
The price is $600
Oct 19 - Oct 20
Total with taxes and fees
3-bedroom house in lovely Matteson with cool AC breeze
A modern kitchen with stainless steel appliances, a marble countertop, and grey cabinetry.

11. 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.
$603 nightly
The price is $639
Oct 29 - Oct 30
Total with taxes and fees
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.

12. 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.
$402 nightly
The price is $426
Oct 18 - Oct 19
Total with taxes and fees
Entire home in Lockport, Illinois
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

13. 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.
$661 nightly
The price is $734
Nov 2 - Nov 3
Total with taxes and fees
Vibrant House, Walk to Train, Game Room
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

14. 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.
$283 nightly
The price is $302
Oct 19 - Oct 20
Total with taxes and fees
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Room

15. 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.
$730 nightly
The price is $817
Oct 18 - Oct 19
Total with taxes and fees
Arcade • Theater • Gym • Office • Sleeps 15
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

16. 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
$444 nightly
The price is $475
Oct 19 - Oct 20
Total with taxes and fees
Romantic Escape - Adult Playhouse with Exotic Dungeon
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

17. 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
$348 nightly
The price is $372
Oct 26 - Oct 27
Total with taxes and fees
LUXE 3 BR, 2 BA + Hot Tub
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

18. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
Forest Park
10.0 out of 10, Exceptional, (2 reviews)
"Great location, great place to stay, host was friendly. Parking was great. Hoping to be able to stay again in the near future."
United States
LEM R.
$452 nightly
The price is $484
Oct 18 - Oct 19
Total with taxes and fees
Classic Forest Park Foursquare < 1 Mi to Blue Line
A building with a sign reading 'Hale Street Cantina' and a brick facade.

19. ✽ 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.
$303 nightly
The price is $321
Oct 19 - Oct 20
Total with taxes and fees
✽ Charming Cottage ✽ close to College/Town/Station
A backyard with a barbecue grill, a dining table with chairs, and a fire pit.

20. 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.
$327 nightly
The price is $346
Oct 19 - Oct 20
Total with taxes and fees
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
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

8/10 Good
"Room smelled so clean and fresh! Our room size was perfect for our stay. Staff was super nice and helped a lot. I did wish a microwave was available in the room. Location was great - nearby stores, cafes and a good bagel spot. Neighborhood was safe and secure. Would recommend the hotel for future stays."
Kanae 2-night trip
Posted 4 hours ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Oak Lawn

Oak Lawn Vacation Homes information

Number of reviews
323
Accommodation
524 Vacation Homes
Lowest Price
$208
Highest Price
$817

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