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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Oak Park vacation rentals

A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

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
$180 nightly
The price is $207
Nov 17 - Nov 18
Total with taxes and fees
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.
$192 nightly
The price is $220
Nov 17 - Nov 18
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.

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.
$217 nightly
The price is $248
Nov 26 - Nov 27
Total with taxes and fees
Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
A two-story house with a brick exterior, a sloped roof, and a front porch.

4. 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
$301 nightly
The price is $344
Nov 12 - Nov 13
Total with taxes and fees
At Home in Oak Park
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

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

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (83 reviews)
"Excellent place to stay!"
United States
Alicia K.
$236 nightly
The price is $270
Nov 10 - Nov 11
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

6. 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
$311 nightly
The price is $356
Nov 16 - Nov 17
Total with taxes and fees
Historic Oak Park Home
A single-story house with a covered porch, a front door, and a small garden area.

7. 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.
$348 nightly
The price is $398
Nov 10 - Nov 11
Total with taxes and fees
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A modern living room with a large flat-screen TV, a brown sofa, a wooden coffee table, and a potted orchid.

8. 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.
$398 nightly
The price is $456
Nov 11 - Nov 12
Total with taxes and fees
Oak Park 3BR/2BA Walk to Frank Lloyd Wright & Hemingway Home, 15 Min to Chicago
A garage with a white door, brick pillars, and a car parked inside.

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

Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
Oak Park
$310 nightly
The price is $355
Nov 12 - Nov 13
Total with taxes and fees
Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

10. 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.
$328 nightly
The price is $376
Nov 16 - Nov 17
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.

11. 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.
$468 nightly
The price is $536
Nov 10 - Nov 11
Total with taxes and fees
Oak Park Victorian by FLW Studio
A modern living room with a flat-screen TV, grey sofas, a coffee table, and a dining area with a table and chairs.

12. Comfy Premier Luxe Retreat with Free Parking

Comfy Premier Luxe Retreat with Free Parking
Oak Park
$214 nightly
The price is $245
Nov 16 - Nov 17
Total with taxes and fees
Comfy Premier Luxe Retreat with Free Parking
A two-story house with a brick exterior, a sloped roof, and a front porch.

13. 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.
$317 nightly
The price is $359
Nov 12 - Nov 13
Total with taxes and fees
Top floor of Historic Oak Park Home /2 Car Garage
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

14. 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
$306 nightly
The price is $351
Nov 9 - Nov 10
Total with taxes and fees
The Oak Park Loft
A building with a white exterior, a visible door, and a tree with blossoms in front.

15. 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.
$442 nightly
The price is $502
Nov 10 - Nov 11
Total with taxes and fees
Top floor of Historic Oak Park Villa /Grge: 2Cars
A building with a white exterior and a tree with white blossoms in front.

16. 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
$420 nightly
The price is $481
Nov 10 - Nov 11
Total with taxes and fees
Historic Oak Park Residence
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.

17. 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
$287 nightly
The price is $355
Nov 11 - Nov 12
Total with taxes and fees
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

18. 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.
$161 nightly
The price is $172
Nov 16 - Nov 17
Total with taxes and fees
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A kitchen with dark wooden cabinets, stainless steel appliances, and a granite countertop.

19. Serene 1-bedroom apartment in Berwyn perfect for a relaxing stay

Serene 1-bedroom apartment in Berwyn perfect for a relaxing stay
Berwyn
$190 nightly
The price is $203
Nov 10 - Nov 11
Total with taxes and fees
Serene 1-bedroom apartment in Berwyn perfect for a relaxing stay
A modern living room with a blue sofa, a patterned rug, and a television.

20. 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.
$166 nightly
The price is $184
Nov 9 - Nov 10
Total with taxes and fees
Great Area Logan Square Apt Games Pets - Sleeps 5
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
"Room was great, as expected and toiletries are always a treat."
Scot 1-night trip
Posted 3 hours ago
Fairmont Chicago at Millennium Park

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 $75 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.