A cityscape with tall buildings, a river, and a bridge at dusk.

Oak Park Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Oak Park vacation rentals

A dining table set with plates, glasses, and a vase of flowers.

1. Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (76 reviews)
"Had an amazing stay and would definitely book again!"
United States
Makenna
The price is SAR 277
SAR 721 total
includes taxes & fees
17 Nov - 18 Nov
Chic Suite/Mins to L Train /Laundry/Free Parking
A glass elevator with a city view.

2. Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (115 reviews)
"Excellent communication from the host, we also appreciated their modern, organized and clean home."
United States
Robin D.
The price is SAR 417
SAR 920 total
includes taxes & fees
14 Dec - 15 Dec
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
A kitchen with a double sink, white cabinets, and a marble backsplash.

3. Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking

Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
Oak Park
9.0 out of 10, Wonderful, (2 reviews)
"We had a very good stay overall and would definitely consider staying here again. The price was excellent for the location, and it was only about a 15–20 minute walk to the train, making it easy to get into the city. The neighborhood felt safe and had several great restaurants nearby.The unit is in an older apartment building, but it’s clear the hosts are putting effort into updating it, and we appreciated the improvements they’ve already made. The host was also very responsive and easy to...
United States
K G.
Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
A two-story house with a prominent evergreen tree in front, surrounded by various shrubs and a driveway.

4. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is SAR 804
SAR 1,337 total
includes taxes & fees
16 Nov - 17 Nov
Historic Oak Park Home
A porch with a wooden bench and chairs, a door with a welcome sign, and a view of neighboring buildings.

5. Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly Yard

Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly Yard
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 SAR 706
SAR 1,453 total
includes taxes & fees
1 Dec - 2 Dec
Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly Yard
A garage with a white door, brick pillars, and a car parked inside.

6. Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking

Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
Oak Park
Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
A modern kitchen with a white countertop, stainless steel appliances, and wooden stools.

7. Oak Park 3BR/2BA Walk to Frank Lloyd Wright & Hemingway Home, 15 Min to Chicago

Oak Park 3BR/2BA Walk to Frank Lloyd Wright & Hemingway Home, 15 Min to Chicago
Oak Park
9.6 out of 10, Exceptional, (5 reviews)
"Great, walkable, location to Concordia University Chicago (River Forest), restaurants and coffee shops, Green Line train to downtown. Beautiful neighborhoods.Upstairs tenants occasionally could be heard walking around, but nothing too bad."
United States
Brian T.
Oak Park 3BR/2BA Walk to Frank Lloyd Wright & Hemingway Home, 15 Min to Chicago
A two-story house with a prominent evergreen tree in front, surrounded by various shrubs and a driveway.

8. First floor of Historic Oak Park Villa, Grge:2Cars

First floor of Historic Oak Park Villa, Grge:2Cars
Oak Park
9.6 out of 10, Exceptional, (26 reviews)
"Very clean, comfortable and nicely located!"
United States
Steve P.
The price is SAR 804
SAR 1,449 total
includes taxes & fees
16 Nov - 17 Nov
First floor of Historic Oak Park Villa, Grge:2Cars
A white two-story house with a porch, steps, and a small table with chairs.

9. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (33 reviews)
"Would stay there again"
United States
Margaret L.
The price is SAR 971
SAR 2,233 total
includes taxes & fees
7 Dec - 8 Dec
Oak Park Victorian by FLW Studio
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a round table and chairs.

10. Comfy Premier Luxe Retreat with Free Parking

Comfy Premier Luxe Retreat with Free Parking
Oak Park
Comfy Premier Luxe Retreat with Free Parking
A two-story house with a brick exterior, a sloped roof, and a front porch.

11. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (14 reviews)
"Great location with parking included"
United States
Melissa
At Home in Oak Park
A modern dining area with a white table, chairs, and a chandelier. There is a painting on the wall and a plant on the sideboard.

12. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.6 out of 10, Exceptional, (7 reviews)
"Room was nice and in a safe location."
United States
Jacob
The price is SAR 232
SAR 1,364 total
includes taxes & fees
15 Nov - 16 Nov
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A living room with a brick fireplace, leather sofa, and a ceiling fan.

13. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
9.8 out of 10, Exceptional, (35 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
The price is SAR 269
SAR 662 total
includes taxes & fees
17 Nov - 18 Nov
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A row of residential houses with a wooden fence in the foreground.

14. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is SAR 225
SAR 725 total
includes taxes & fees
16 Nov - 17 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5
Step into a bright, airy space where comfort and style flow seamlessly from the cozy living area into a chic dining room. Whether you're curled up on the sectional with a blanket and coffee or gathering around the modern wood table for a meal with fr

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

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
9.8 out of 10, Exceptional, (8 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is SAR 330
SAR 2,021 total
includes taxes & fees
15 Nov - 16 Nov
Theater • Game Room • Gym • Firepit • 4BR Home
A single-story house with a front porch, a staircase leading to the entrance, and a driveway.

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, (36 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A pool table with surrounding arcade machines, including a 'Game Room' sign.

17. Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.6 out of 10, Exceptional, (5 reviews)
"Everyone was super happy with the house and the location."
United States
Rhiannon
The price is SAR 417
SAR 1,844 total
includes taxes & fees
16 Nov - 17 Nov
Game Room • Fire-pit • Playground • Gym • Billiard
A two-story house with a front porch, a staircase leading to the second floor, and a well-maintained garden.

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

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is SAR 908
SAR 1,782 total
includes taxes & fees
16 Nov - 17 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line
A desk with a computer monitor, keyboard, mouse, a lamp, a mug, a plant, and a clock.

19. Private Workspace • Sleeps 4 • Modern and Stylish

Private Workspace • Sleeps 4 • Modern and Stylish
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay here. The communication was great. Check-in was flawless. We were able to find free parking close by. The listing is accurate, and the location was perfect for our visit to Chicago. We would definitely stay again. Well-equipped kitchen, in-unit laundry, plug strips and extra bedding all were appreciated."
United States
Karin S.
The price is SAR 371
SAR 1,255 total
includes taxes & fees
21 Nov - 22 Nov
Private Workspace • Sleeps 4 • Modern and Stylish
A room with arcade machines, a foosball table, and a neon sign indicating 'GAME ON'.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful night, boys loved the arcade area."
United States
Anonymous traveler
The price is SAR 570
SAR 3,340 total
includes taxes & fees
17 Nov - 18 Nov
Sleeps 18 • 8BR • Game Room • Gym • Theater
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 Park Hotel Reviews

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Very much enjoyed our stay. Staff was amazing!! Breakfast was excellent."
Frances 3-night trip
Posted less than an hour ago
Fairmont Chicago at Millennium Park

Frequently asked questions

Are there vacation rentals in Oak Park?

Yes, we have vacation rentals in Oak Park close to Oak Park Conservatory, or you can choose a secluded option if you're looking for extra privacy while you relax. Tourists like the array of shops and top-notch restaurants in Oak Park. While you're here, grab a bite or have a drink at the cafes.

What are some of the best vacation rentals that Oak Park has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This vacation home rental outside of Oak Park is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Oak Park?

With 28 Expedia vacation rentals, you're sure to find just the right place for your Oak Park stay.

What’s there to see and do in Oak Park?

Cultural attractions include Ernest Hemingway Museum and House and Madison Street Theatre, whereas Oak Park Conservatory and Mills Park are a couple of picturesque spots to enjoy the outdoors. Other popular places to visit in the area include Wrigley Field and Soldier Field.

What’s a vacation rental in Oak Park like?

Vacation rentals are private properties you can stay in for several days or longer in Oak Park. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.