Oak Park holiday lettings

We found 2,876 holiday rentals — enter your dates for availability

Discover a selection of 34 homes, 52 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.
  • 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, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

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!

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.

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

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.

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 Michigan Avenue 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)
  • Rainbow Falls Waterpark (13.8 mi / 22.3 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 most popular type of holiday rental accommodation in Oak Park?
Apartments are the most popular style of holiday rental in Oak Park, according to our data. Even if you have a different vision in mind, Vrbo has properties in loads of sizes and shapes. Look through our options to find your perfect match.
How much does it cost to rent a holiday rental in Oak Park?
Several things determine what you'll pay for your holiday rental in Oak Park, including the type of property, season and length of stay. However, all of our holiday homes have one thing in common --- amazing value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Oak Park?
When you travel and the size and style of the property will influence the cost of your beachside holiday rental. Put in your Oak Park travel dates to see all your options on Vrbo. Can't live without a private pool? Use the filters to pick the features and amenities you need.
Are there pet-friendly holiday rentals in Oak Park?
Yes. There are. You can pick from 52 holiday rentals that allow pets in Oak Park. Many of our pet-friendly holiday rentals even come with a garden for your fur child to run around in, special dog beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your pawfect place on Vrbo.
Can I rent a house with a pool in Oak Park?
Add a new level of fun to your getaway by booking one of the four houses with a private pool in Oak Park. Use our handy search filter to find the kind of property you want on Vrbo, and then spend your downtime splish-splashing around in a swimming pool that's all your own.
What are popular rental amenities in Oak Park?
A garden, a nearby river and a firepit head the list of most popular rental amenities in Oak Park. Whether you're planning to travel as a party of one, with your significant other or a bunch of friends, Vrbo will help you find a holiday rental that suits your tastes with all the features you need.
Are there large group holiday rentals in Oak Park?
With two properties that can host 10 guests or more in Oak Park, you won't have to keep anyone off the invite list. From holidays with the extended family to special events like anniversary parties and weddings, Vrbo can help you find a large group rental to suit the occasion.
Are there holiday rentals in Oak Park that welcome kids?
With 51 family-friendly holiday rentals available in Oak Park, now is the perfect time to introduce your children to the wonders of travel. Simply click on our "Properties good for families" filter box to search for stays that feature amenities ideal for holidaying families, like multiple bedrooms, patios, bunk beds and hot tubs.
What are the top attractions for families in Oak Park?
Keeping the kids entertained during your Oak Park holiday is a snap with these cool family-friendly attractions:

  • Chicago Riverwalk
  • Shedd Aquarium
  • Field Museum of Natural History

Are there one-bedroom holiday rentals in Oak Park?
Yes, you can take your pick from 15 one-bedroom rentals in Oak Park. Whether you're on the lookout for a secluded cottage or an upmarket condo, our one-bedroom properties are just right if you don't require loads of space. One of the best parts about having your own pad? You won't need to share your adventure with strangers.
Can I find two-bedroom holiday rentals in Oak Park?
Gather your nearest and dearest and enjoy a relaxing escape in one of the 18 two-bedroom holiday rentals Oak Park has to offer.
Are there holiday rentals with WiFi in Oak Park?
Whether you'd like to keep up with the news, make a video call or surf your social networks, there are 16 holiday homes with WiFi in Oak Park. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Oak Park?
You'll have your pick of 48 holiday homes with air conditioning in Oak Park giving you that gentle, cool breeze and extra element of comfort. Just enter your preferred travel dates and then use our handy filter tool to search for stays with air conditioning.
How old do you have to be to rent a holiday rental in Oak Park?
The minimum age is usually 16, 18 or 21. It can differ from one property to another on Vrbo, so check the rules of your preferred Oak Park stay before booking your trip.
How long can I rent a holiday rental in Oak Park for?
The amount of time you can book an Oak Park holiday home for is down to each property. Simply put in your preferred travel dates to view options offering longer term stays. They feature all you require to make your extended trip more comfortable and convenient, like kitchens and yards. Some holiday rentals may also offer weekly or monthly discounts, so you can stay longer for less money.

More Holiday Rentals ideas

People also search for