Oak Park holiday rentals

We found 2,755 holiday rentals — enter your dates for availability
Discover a selection of 28 homes, 76 apartments and other holiday rentals in Oak Park that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the amenities that you expect and more, which might include parking and a hot tub. No matter what you're looking for, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Oak Park

Showing deals for:1 Jan - 8 Jan

Room
Our downtown Townhouse is in an amazing location
Interior
Dining
Exceptional
(92 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
AU$10,318
for 7 nights, 1 home
AU$1,474 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Outdoors at night
River North Luxury Living
French Bistro and Wine Bar - right downstairs
Interior
Exceptional
(106 reviews)

River North's Rock N' Roll - In The Heart of the City

Chicago

7% off
AU$5,324
for 7 nights, 1 apartment
AU$761 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Interior
Exterior
Private kitchen
Dining
Exceptional
(26 reviews)

Beautiful Berwyn Bungalow Close to Downtown Chicago

Berwyn

8% off
AU$3,552
for 7 nights, 1 home
AU$507 per night
includes taxes & fees
Beautiful Berwyn Bungalow Close to Downtown Chicago
Dining
Exterior
Terrace/patio
Interior
Exceptional
(14 reviews)

Spacious 6BR South Loop Luxury Suite Near McCormick Place & Soldier Field for 12

Chicago

7% off
AU$7,652
for 7 nights, 1 apartment
AU$1,093 per night
includes taxes & fees
Spacious 6BR South Loop Luxury Suite Near McCormick Place & Soldier Field for 12
Living area
Interior
Room
Dining
Exceptional
(25 reviews)

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Berwyn

8% off
AU$2,425
for 7 nights, 1 apartment
AU$346 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Sunny Bay Window
Polk Street
Room 2 Queen bed black out curtains vintage snd Original art and a TV
Open Concept Living Room
Exceptional
(315 reviews)

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Chicago

7% off
AU$2,851
for 7 nights, 1 apartment
AU$407 per night
includes taxes & fees
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Downstairs living room
Downstairs living area
Kitchen (upstairs)
Fun Mirror Wall Upstairs
Exceptional
(100 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
AU$14,546
for 7 nights, 1 apartment
AU$2,078 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Kitchen
Living Room
Bedroom 1 (King Size) + 55Inch TV
Patio Deck 2
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$7,043
for 7 nights, 1 home
AU$1,006 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Room
Upon entering lobby there will be 2 doors. You have rented the apartment on the
Interior
View from sidewalk
Exceptional
(11 reviews)

5 bedroom with 5 beds and 2 bathrooms

Oak Park

12% off
AU$5,367
for 7 nights, 1 apartment
AU$767 per night
includes taxes & fees
5 bedroom with 5 beds and 2 bathrooms
Room
Interior
Dining
Private kitchen
Wonderful
(41 reviews)

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Berwyn

8% off
AU$2,861
for 7 nights, 1 apartment
AU$409 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Room
Private kitchen
Dining
Exterior detail
Exceptional
(69 reviews)

Steps from the “L” train to Wrigley & Downtown

Chicago

7% off
AU$4,747
for 7 nights, 1 apartment
AU$678 per night
includes taxes & fees
Steps from the “L” train to Wrigley & Downtown
Upscale kitchen with an equally spacious dining room
5 minutes drive to McCormick Place (0.9 miles)
Enjoy your stay in the well appointed living room with a 55" Roku Smart TV
Upscale kitchen with an equally spacious dining room
Wonderful
(9 reviews)

23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown

Chicago

7% off
AU$3,434
for 7 nights, 1 apartment
AU$491 per night
includes taxes & fees
23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
Room
Dining
Living area
Living area
Wonderful
(21 reviews)

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Berwyn

8% off
AU$2,606
for 7 nights, 1 apartment
AU$372 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Living Room with 60 in Smart TV
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Living Room with 60 in Smart TV
Living Room with 60 in Smart TV
Exceptional
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
AU$9,500
for 7 nights, 1 home
AU$1,357 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Dining
Living area
Interior
Private kitchen
Very good
(5 reviews)

Chicago style apt/Near Hosp/ORD/MDW/DT

Berwyn

8% off
AU$2,632
for 7 nights, 1 apartment
AU$376 per night
includes taxes & fees
Chicago style apt/Near Hosp/ORD/MDW/DT
Private kitchen
Belmont Harbor
Living area
Living area
Exceptional
(193 reviews)

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Chicago

8% off
AU$5,762
for 7 nights, 1 home
AU$823 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Private kitchen
Exterior detail
Dining
Interior
Exceptional
(12 reviews)

Historic feel, Modern comfort Walk to parks and food in beautiful Chicago

Chicago

6% off
AU$2,017
for 7 nights, 1 apartment
AU$288 per night
includes taxes & fees
Historic feel, Modern comfort Walk to parks and food in beautiful Chicago
Well stocked kitchen with Keurig coffee maker, microwave, water filter and more
Living area
Bedroom #4 with a double and single bed
Interior
Exceptional
(22 reviews)

1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off
AU$5,158
for 7 nights, 1 apartment
AU$737 per night
includes taxes & fees
1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Dining
Private kitchen
Interior
Interior
Wonderful
(50 reviews)

Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!

Chicago

7% off
AU$5,557
for 7 nights, 1 home
AU$794 per night
includes taxes & fees
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Dining
Living area
Private kitchen
Interior
Exceptional
(23 reviews)

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Berwyn

8% off
AU$2,476
for 7 nights, 1 apartment
AU$354 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Living area
Dining
Living area
Terrace/patio
Exceptional
(7 reviews)

The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.

Chicago

7% off
AU$11,182
for 7 nights, 1 apartment
AU$1,597 per night
includes taxes & fees
The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
The side view
Night View
A Viking Stove and Quartz Countertops, You decide whats cooking.
Magnificent tunes
Exceptional
(26 reviews)

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

Oak Park

12% off
AU$3,516
for 7 nights, 1 apartment
AU$502 per night
includes taxes & fees
First floor of Historic Oak Park Villa, Grge:2Cars
The light corridor combines connection with privacy.
Cheney Mansion 4 min walk
Drop in tennis courts three blocks away.
Ample garage space is rare in an urban environment.
Exceptional
(24 reviews)

Top floor of Historic Oak Park Home /2 Car Garage

Oak Park

12% off
AU$3,277
for 7 nights, 1 apartment
AU$468 per night
includes taxes & fees
Top floor of Historic Oak Park Home /2 Car Garage
Private kitchen
Living area
Dining
Room
Exceptional
(14 reviews)

Ridgeland Retreat/ Street level Apt easy access

Berwyn

8% off
AU$3,765
for 7 nights, 1 apartment
AU$538 per night
includes taxes & fees
Ridgeland Retreat/ Street level Apt easy access

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Oak Park getaway

The area's architecture and temples are just some of the reasons to come on holiday to Oak Park. Well known for its restaurants, shopping and local tours, this walkable city won't disappoint. Wrigley Field and Soldier Field are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Oak Park

Are you hoping to find top things to see and do in the city? Venture out of your holiday home and check out everything that makes Oak Park a fun spot to go on holiday. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Galloping Ghost (6 mi / 9.6 km)
  • Oak Brook Golf Course (8.1 mi / 13 km)
  • Lincoln Park Zoo (8.1 mi / 13.1 km)
  • The Dome at the Parkway Bank Sports Complex (8.1 mi / 13.1 km)
  • The Glen Club (14.4 mi / 23.2 km)
  • Harborside International Golf Center (16.3 mi / 26.3 km)

Exploring the natural features in Oak Park

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Oak Park is a great place to get outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (8.3 mi / 13.3 km)
  • Grant Park (8.4 mi / 13.6 km)
  • Garfield Park (3.4 mi / 5.5 km)
  • Garfield Park Conservatory (3.4 mi / 5.5 km)
  • Humboldt Park (4.4 mi / 7.1 km)
  • Anna and Frederick Douglass Park (4.6 mi / 7.4 km)

Transport options to and around Oak Park

Fly into Chicago Midway Airport (MDW), the closest airport, located 7 mi (11.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Chicago O'Hare International Airport (ORD), which is 8.9 mi (14.4 km) away.

If you're travelling by train, you can make your way to Oak Park Station. You can get around Oak Park by jumping on the metro at Ridgeland Station (Green Line), Oak Park Station (Green Line) or Oak Park Station (Blue Line).

Frequently asked questions

What is the best area to stay in Oak Park when booking a holiday rental?
When considering a holiday rental in Oak Park, Illinois, one of the most appealing areas to stay in is the historic district. This neighbourhood is renowned for its stunning architecture, featuring a wealth of homes designed by the famous architect Frank Lloyd Wright. Visitors can explore the Frank Lloyd Wright Home and Studio, which offers a fascinating insight into his life and work.Another excellent choice is the area around Oak Park Avenue, which boasts a vibrant setting with an array of shops, cafés, and restaurants. Here, you'll find the Oak Park Arts District, a hub for local artists and cultural events, making it an exciting spot for those looking to immerse themselves in the local arts scene. Additionally, the nearby Pleasant Home, a beautiful historic mansion, is a must-visit for architecture enthusiasts.In terms of accommodation, Oak Park offers a variety of holiday rentals, ranging from charming historic homes to modern apartments. This diverse selection caters to different preferences and budgets.
What is the most popular type of holiday rental accomodation in Oak Park?
In Oak Park, apartments are the most popular type of holiday rental, with around 220 available across the area. These apartments are typically found in charming neighbourhoods close to top attractions like the Frank Lloyd Wright Home and Studio and the Ernest Hemingway Birthplace. Most units come equipped with fully functional kitchens, spacious living areas, and often include amenities such as Wi-Fi and laundry facilities.For those seeking more space, approximately 108 holiday houses are also on offer, which generally feature multiple bedrooms, private gardens, and outdoor seating areas—ideal for families or groups. Additionally, there are several condos available, providing an alternative for travellers looking for modern living spaces.
Are there any family house rentals in Oak Park?
In Oak Park, Illinois, there are a variety of family-friendly house rentals available, with approximately 56 properties to choose from. This charming suburb is known for its historic architecture and proximity to the vibrant city of Chicago. Many homes in the area offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play or enjoy a barbecue.Visitors will appreciate amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay. The locale is also close to several parks, including Scoville Park, which features playgrounds and walking paths, making it ideal for families looking to enjoy outdoor activities. Additionally, the Frank Lloyd Wright Home and Studio is a nearby point of interest for those interested in architecture and history.
Can I rent a holiday home with a pool or hot tub in Oak Park?
In Oak Park, Illinois, there are several holiday homes available for rent that feature pools and hot tubs. This charming suburb, known for its Frank Lloyd Wright architecture and vibrant community, offers a range of properties suitable for families or groups looking to enjoy a relaxing stay. Many rentals come equipped with private pools, hot tubs, and outdoor spaces great for entertaining or unwinding after a day of exploring the area. Additionally, amenities such as fully equipped kitchens and comfortable living areas are typically included, providing a homely atmosphere.
Are there pet-friendly house rentals in Oak Park?
In Oak Park, travellers will find a variety of pet-friendly house rentals, with around 31 options available. This charming suburb of Chicago is known for its historic architecture and vibrant community atmosphere. Many of the holiday rentals come equipped with modern amenities such as fully furnished kitchens, spacious living areas, and outdoor spaces, making them suitable for families and groups travelling with pets.Oak Park itself is home to several parks, including Scoville Park and Austin Gardens, which provide ample opportunities for outdoor activities with your furry friends. These parks feature walking paths, open spaces, and lovely shaded areas, superb for leisurely strolls or picnics. Additionally, the area boasts pet-friendly cafes and shops, adding to the convenience and enjoyment for those travelling with pets.
Are there any remote work holiday rentals in Oak Park?
In Oak Park, Illinois, there are ample remote work holiday rentals available, with around 316 options to choose from. This suburb of Chicago is well-known for its rich architectural history and vibrant arts scene, making it an appealing destination for those looking to blend work with leisure. Many properties are equipped with essential amenities for remote work, such as free Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living areas that facilitate productivity.Visitors will appreciate the proximity to top landmarks, including the Frank Lloyd Wright Home and Studio, which showcases the famed architect's work. The area also features charming parks and local cafes, providing great spots for breaks during the workday. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Oak Park?
In Oak Park, popular holiday rental amenities include well-equipped kitchens, which allow guests to prepare their own meals conveniently. Many properties also offer onsite parking for easy access, as well as coffee and tea makers to enjoy warm beverages at any time. For those needing to work or study, rentals typically come with a desk, and outdoor spaces like decks or patios are common, providing a pleasant area to relax and enjoy the surroundings.
When is the best time to visit Oak Park for a holiday rental?
The best time to visit Oak Park for a holiday rental is during the vibrant summer months of May to July, with July being particularly popular. This period attracts families and cultural enthusiasts eager to explore the charming architecture, delightful parks, and rich history of the area. Visitors can enjoy warm temperatures, typically ranging from 20 to 30 degrees Celsius, superb for outdoor activities such as strolling through the Frank Lloyd Wright Home and Studio or relaxing in the scenic parks.In July, Oak Park buzzes with energy, hosting various local events and festivals that celebrate the community's artistic spirit. You'll find plenty of opportunities to engage with local culture, from art walks to farmers' markets, making it an excellent time for those seeking a lively option.For those looking for a more budget-friendly option, consider visiting in November. This quieter month provides a great experience to enjoy Oak Park's charming streets adorned with autumn leaves, allowing for reflective walks and less crowded attractions. The cooler temperatures can be inviting for cosy indoor activities, such as visiting local museums or enjoying the town's culinary scene.
What are the top attractions in Oak Park?
In Oak Park, visitors can explore a rich array of attractions, particularly known for its architectural significance and cultural heritage. The Frank Lloyd Wright Home and Studio is a prominent highlight, where the famed architect lived and worked, offering insights into his innovative designs. Nearby, the Unity Temple, another of Wright's masterpieces, showcases his unique approach to modern architecture.The Ernest Hemingway Museum and Birthplace is also a must-visit, celebrating the life and works of the renowned author. This historic site provides a glimpse into Hemingway's early years and the influences that shaped his literary career.For those interested in outdoor activities, Mills Park offers beautiful green spaces, walking paths, and a playground, making it a lovely spot for families. Additionally, the Oak Park Arts District features a vibrant collection of galleries, studios, and shops, great for those looking to immerse themselves in local art and culture.
Are all fees included in the Oak Park holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Oak Park holiday homes with parking?
Stayz offers a wide selection of holiday homes in Oak Park with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Oak Park holiday homes?
You can find great discounts on holiday homes in Oak Park on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Oak Park holiday home booking on Stayz?
To find Oak Park holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Oak Park?
A long-stay holiday home in Oak Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Oak Park holiday home?
Book your Oak Park holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Oak Park?
Prices for holiday homes in Oak Park vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Oak Park to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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