Oak Park Holiday 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 holiday 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
The price is AU$311
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 AU$330
includes taxes & fees
17 Nov - 18 Nov
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.
The price is AU$421
includes taxes & fees
30 Nov - 1 Dec
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
The price is AU$497
includes taxes & fees
12 Nov - 13 Nov
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.
The price is AU$406
includes taxes & fees
16 Nov - 17 Nov
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
The price is AU$519
includes taxes & fees
16 Nov - 17 Nov
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.
The price is AU$584
includes taxes & fees
1 Dec - 2 Dec
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.
The price is AU$674
includes taxes & fees
12 Nov - 13 Nov
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
The price is AU$519
includes taxes & fees
12 Nov - 13 Nov
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.
The price is AU$535
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.

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.
The price is AU$773
includes taxes & fees
10 Dec - 11 Dec
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
The price is AU$363
includes taxes & fees
16 Nov - 17 Nov
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.
The price is AU$525
includes taxes & fees
12 Nov - 13 Nov
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
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.
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
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
The price is AU$518
includes taxes & fees
12 Nov - 13 Nov
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.
The price is AU$257
includes taxes & fees
16 Nov - 17 Nov
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
The price is AU$307
includes taxes & fees
18 Nov - 19 Nov
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.
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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Find holiday rentals that suit your style

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Top Oak Park Hotel Reviews

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago

10/10 Excellent

The hotel has been reburbished beautifully. Staff have been amazing letting us hang out in the lounge waiting for our train departure. Great location, fantastic cafe next door, great bars in the area. Only a short walk to Michigan Avenue for hop on hop off bus.
Australia
Cherrie
Reviewed October 12, 2024
Hilton Vacation Club Hotel Blake Chicago

Find out more about Oak Park

Everything you need to know about Oak Park holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Park holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Oak Park holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oak Park holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oak Park holiday rentals we have selected for you start as low as AU$256 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oak Park rentals

At Expedia, we put the best Oak Park holiday 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 holiday.

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.

Frequently Asked Questions

Are there holiday rentals in Oak Park?

Yes, there are holiday rentals in Oak Park close to Oak Park Conservatory, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Oak Park has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Oak Park is located in the city centre, and has a balcony, a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Oak Park?

With 28 Expedia holiday rentals, you're guaranteed 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 holiday rental in Oak Park like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oak Park. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.