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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Oak Park vacation rentals

Terrace/patio

1. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
$289 nightly
The price is $330
Oct 25 - Oct 26
Total with taxes and fees
At Home in Oak Park
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

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

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.4 out of 10, Exceptional, (71 reviews)
"Easy access to the Green Line."
United States
Michael
$211 nightly
The price is $242
Nov 2 - Nov 3
Total with taxes and fees
Chic Suite/Mins to L Train /Laundry/Free Parking
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

3. 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
$258 nightly
The price is $296
Oct 27 - Oct 28
Total with taxes and fees
Historic Oak Park Home
A glass elevator with a city view.

4. 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, (114 reviews)
"Very clean, spacious living area, and convenient location"
United States
Clara B.
$254 nightly
The price is $291
Oct 13 - Oct 14
Total with taxes and fees
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
A modern living room with a grey sofa, two armchairs, a coffee table, and a dining area with a wooden table and chairs.

5. 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.
$211 nightly
The price is $242
Oct 25 - Oct 26
Total with taxes and fees
Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

6. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (81 reviews)
"Excellent place to stay!"
United States
Alicia K.
$270 nightly
The price is $309
Oct 19 - Oct 20
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
A modern living room with a large flat-screen TV, a brown sofa, a wooden coffee table, and a potted orchid.

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, (4 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.
$433 nightly
The price is $495
Oct 7 - Oct 8
Total with taxes and fees
Oak Park 3BR/2BA Walk to Frank Lloyd Wright & Hemingway Home, 15 Min to Chicago
A two-story house with a visible front porch and a large evergreen tree in the foreground.

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.
$297 nightly
The price is $340
Oct 27 - Oct 28
Total with taxes and fees
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.
$596 nightly
The price is $682
Oct 21 - Oct 22
Total with taxes and fees
Oak Park Victorian by FLW Studio
Private kitchen

10. 1BR Apartment - Walk to Shops - Downtown OAK PARK

1BR Apartment - Walk to Shops - Downtown OAK PARK
Oak Park
9.2 out of 10, Wonderful, (44 reviews)
"Great location! Enjoyed my stay!"
United States
Shannon H.
$223 nightly
The price is $255
Oct 27 - Oct 28
Total with taxes and fees
1BR Apartment - Walk to Shops - Downtown OAK PARK
A building with a white exterior and a tree with white blossoms in front.

11. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
$337 nightly
The price is $386
Oct 21 - Oct 22
Total with taxes and fees
Historic Oak Park Residence
A modern living room with a sectional sofa, a coffee table, and a TV.

12. 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.
$203 nightly
The price is $232
Oct 13 - Oct 14
Total with taxes and fees
Attractive Coach House Apartment for rent in Oak Park.
A single-story house with a covered porch, a front door, and a small garden area.

13. 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.
$315 nightly
The price is $361
Nov 3 - Nov 4
Total with taxes and fees
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Living area

14. Mins to DT & Frank Lloyd Wright

Mins to DT & Frank Lloyd Wright
Oak Park
8.8 out of 10, Excellent, (3 reviews)
"Great location here. Close to downtown oak Park. Easy walking."
United States
John N.
$210 nightly
The price is $240
Oct 27 - Oct 28
Total with taxes and fees
Mins to DT & Frank Lloyd Wright
A modern kitchen with a dishwasher, a sink, and a coffee maker.

15. Studio Mins Walk to DT OAK PARK

Studio Mins Walk to DT OAK PARK
Oak Park
$417 nightly
The price is $477
Oct 7 - Oct 8
Total with taxes and fees
Studio Mins Walk to DT OAK PARK
A view of a historic building with a prominent tower, seen through a window with a view of trees and a building in the foreground.

16. The Oak Park Loft, Including Garage

The Oak Park Loft, Including Garage
Oak Park
10.0 out of 10, Exceptional, (11 reviews)
"Private, historic, well, equipped, comfortable, and the owners were very friendly and accessible."
United States
James
$238 nightly
The price is $268
Oct 28 - Oct 29
Total with taxes and fees
The Oak Park Loft, Including Garage
A room with a green table, chairs, a tripod, and a poster on the wall.

17. Top floor of Historic Oak Park Villa /Grge: 2Cars

Top floor of Historic Oak Park Villa /Grge: 2Cars
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The property was beautiful, spacious, warm, and very charming!"
United States
Sarah S.
$391 nightly
The price is $444
Oct 18 - Oct 19
Total with taxes and fees
Top floor of Historic Oak Park Villa /Grge: 2Cars
A bedroom with a bed, bedside tables, a ceiling fan, a window with curtains, and a radiator.

18. Top floor of Historic Oak Park Home /2 Car Garage

Top floor of Historic Oak Park Home /2 Car Garage
Oak Park
9.6 out of 10, Exceptional, (24 reviews)
"Our stay was wonderful. The location with parking was perfect."
United States
Joan W.
$344 nightly
The price is $390
Oct 25 - Oct 26
Total with taxes and fees
Top floor of Historic Oak Park Home /2 Car Garage
A modern living room with a flat-screen TV, grey sofas, a coffee table, and a dining area with a table and chairs.

19. Comfy Premier Luxe Retreat with Free Parking

Comfy Premier Luxe Retreat with Free Parking
Oak Park
$238 nightly
The price is $272
Oct 26 - Oct 27
Total with taxes and fees
Comfy Premier Luxe Retreat with Free Parking
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

20. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
$206 nightly
The price is $236
Oct 28 - Oct 29
Total with taxes and fees
The Oak Park Loft
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

River Hotel

River Hotel

10/10 Excellent
"Wonderful experience. So close to the river walk and activities. Staff was so helpful and attentive and property was clean and comfy! Highly recommend!"
Susan 4-night trip
Posted 3 hours ago
River Hotel

Find out more about Oak Park

Everything you need to know about Oak Park vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Park vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oak Park vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oak Park vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oak Park. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Oak Park in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $72 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oak Park rentals

At Expedia, we put the best Oak Park vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oak Park rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oak Park vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oak Park. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.