Oak Park holiday lettings

We found 2,875 holiday rentals — enter your dates for availability

Discover a selection of 29 homes, 69 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:3 Jul - 10 Jul

Image gallery for Enamored in Elmhurst

Living area
10 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)

Enamored in Elmhurst

Elmhurst

8% off
Price is £2,491
for 7 nights, 1 home
£356 per night
includes taxes & fees
Enamored in Elmhurst

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Why visit Oak Park

  • Charming outdoor spaces: Enjoy leisurely walks in the picturesque Oak Park Gardens, perfect for families and solo visitors alike.
  • Rich historical significance: Explore the area’s historic buildings and vibrant neighbourhoods, showcasing its fascinating past.
  • Proximity to Chicago: Experience the lively city atmosphere of Chicago while retreating to the tranquillity of Oak Park.
  • Diverse accommodation options: Choose from stylish apartments, cosy holiday homes, and modern condos tailored to your needs.
  • Family-friendly activities: Engage in a variety of attractions that cater to visitors of all ages.

Popular types of accommodation in Oak Park

Planning a getaway to Oak Park? You’re in for a treat! This charming area offers a variety of accommodation options, including stylish apartments, cosy houses, and modern condos. Whether you're after spacious bedroom apartments, ground floor options, or shared accommodations, you'll find plenty of choices tailored to your needs. Enjoy your holiday rentals with added amenities for a comfortable stay. Explore your options and make the most of your Oak Park experience!

  • Apartments: The top choice for visitors in Oak Park, offering a home-like atmosphere with all essential amenities, perfect for couples or families.
  • Houses: A popular option for those seeking privacy and space, ideal for larger groups or families wanting a more personalised stay.
  • Condos: A desirable choice featuring modern facilities and convenient locations, suitable for travellers who appreciate a bit of luxury.
  • Cottages: Charming and cosy, these quaint properties provide a delightful retreat for guests looking to relax in a picturesque setting.**

Top attractions near Oak Park

Oak Park, Illinois, is an excellent destination for family-friendly, outdoor, and city-themed holidays. Visitors can explore urban parks, historic buildings, and event venues, all while enjoying a rich cultural experience. Highlights include the beautiful Oak Park Gardens, perfect for leisurely strolls or family outings. Whether you're travelling solo or with loved ones, Oak Park offers a variety of attractions to ensure a memorable visit.

  • Willis Tower: An iconic skyscraper offering breathtaking views of the Chicago skyline. The Skydeck allows visitors to step onto glass ledges for an exhilarating experience, providing a unique perspective of the city below.
  • Donald E. Stephens Convention Center: A prominent venue for events and conferences, it exudes a professional atmosphere. Its expansive spaces host a variety of exhibitions and gatherings, perfect for networking and engaging with diverse industries.
  • University of Illinois Chicago: A historic institution that blends culture and education. The campus features striking architecture and vibrant student life, making it an enriching place to explore the arts and community events.

Things to do recommended for couples

For a romantic getaway in Oak Park, indulge in a concert at the Aragon Ballroom, savour a meal at the Historic Michael Jordan Restaurant, or explore the charming Lynfred Winery for wine tasting. Each venue offers a unique atmosphere perfect for couples seeking memorable experiences.

Things to do recommended for families

Families visiting Oak Park can immerse themselves in the excitement of Wrigley Field, only 5.0km away, enjoy wellness at Norridge Park District, 3.7km away, and have a thrilling adventure at Galloping Ghost, also 3.7km distant, perfect for a fun-filled day.

Things to do recommended for groups

Experience vibrant shopping at the Fashion Outlets of Chicago, just 5.0km from Oak Park. Enjoy a cultural evening at the Madison Street Theatre, right in Oak Park, or share laughs with the family at Second City, also 5.0km away. A perfect blend of fun awaits!

What do I need to keep in mind when booking a vacation in 'Oak Park

If you're planning a trip with friends, family, pets, or are considering an extended stay, be sure to apply the appropriate filters to meet your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Oak Park with a group: Think about how many bedrooms you'll require, as well as any amenities you might desire, such as a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Oak Park with young kids: Travelling with young children can be quite a task. It's important to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, you might want to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Oak Park: For many, a family holiday wouldn’t feel complete without their furry companion. If that resonates with you, we recommend exploring Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Oak Park: If you're seeking holiday rentals with discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding amenities such as a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay near Oak Park

Oak Park, Illinois, offers a delightful blend of family-friendly activities and urban charm, making it an ideal holiday destination. Explore the rich history and vibrant neighbourhoods, including the scenic Spring Hills and the welcoming atmosphere of Stanstead Abbotts. With its close proximity to Chicago, visitors can also enjoy the city's dynamic vibe while returning to the tranquillity of Oak Park. This region promises a memorable experience for families and explorers alike.

  • South Austin: A vibrant neighbourhood located a mere mile from Oak Park, South Austin is a delightful destination for families seeking outdoor adventures and a city-themed experience. Visitors can enjoy various recreational parks, where children can play and families can picnic. The area is also known for its lively music concerts that celebrate local talent. Notable attractions include a sports facility stadium and an urban park, where you can relax and take in the local atmosphere.
  • Austin: Another neighbourhood just 1.6km from Oak Park, Austin offers a rich blend of family-friendly activities and outdoor pursuits. The area boasts a variety of recreation parks perfect for a day out, along with theatres showcasing local productions. The arena entertainment facility draws crowds for various events, ensuring there's always something happening. Close by, you’ll find an urban park and a stadium, perfect for catching a game or enjoying some fresh air.
  • Forest Park: Situated two miles from Oak Park, Forest Park is a charming city that welcomes families with a wealth of outdoor activities and city-themed attractions. Visitors can engage in educational experiences and enjoy the local arena entertainment facility. The extensive recreation parks are ideal for leisurely strolls or active play. Don’t miss the local stadium and sports facility, as well as the peaceful urban park that provides a perfect backdrop for relaxation and exploration.

Best time to go to Oak Park

If you're planning a trip to Oak Park, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.0°F (-3.9°C)Light RainMostly CloudySlightly LowSlightly Low
February26.8°F (-2.9°C)Light RainMostly CloudyAverageSlightly Low
March37.9°F (3.3°C)Light RainMostly CloudyAverageSlightly Low
April47.3°F (8.5°C)Light RainMostly SunnySlightly HighAverage
May58.6°F (14.8°C)Light RainMostly SunnyAverageAverage
June68.9°F (20.5°C)Light RainMostly SunnySlightly HighSlightly High
July74.1°F (23.4°C)Light RainMostly SunnySlightly HighSlightly High
August73.6°F (23.1°C)Light RainMostly SunnyAverageSlightly High
September67.3°F (19.6°C)Light RainMostly SunnyAverageAverage
October54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
November41.9°F (5.5°C)Light RainMostly SunnySlightly LowAverage
December32.4°F (0.2°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, opting for a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient area for you to plan new journeys, keep track of your arrangements, or manage your bookings. The properties you’ve saved or reserved are neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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 McCormick Place 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)
  • Dave & Buster's (7.9 mi / 12.7 km)
  • Lincoln Park Zoo (8.1 mi / 13.1 km)
  • The Dome at the Parkway Bank Sports Complex (8.1 mi / 13.1 km)
  • Adagio Teas (12.4 mi / 20 km)
  • Pirates Cove Childrens Theme Park (14.3 mi / 23.1 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.
How much does it cost to rent a holiday home in Oak Park?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oak Park to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Oak Park holiday house rentals?
You can find great discounts on house rentals in Oak Park on Vrbo, 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.
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.
Can I find long-stay holiday rentals in Oak Park?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 Vrbo.
Are there any Oak Park holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
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.
How early should I book a Oak Park holiday rental?
Book your Oak Park holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Oak Park home rental booking on Vrbo?
To find Oak Park holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Oak Park holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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