Oak Park holiday homes

We found 2,797 holiday rentals — enter your dates for availability

Discover a selection of 30 homes, 55 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:26 Dec - 2 Jan
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Why visit Oak Park

  • Architectural Wonders: Discover stunning Frank Lloyd Wright-designed homes that showcase innovative architecture.
  • Oak Park Conservatory: Relax in this beautiful conservatory filled with exotic plants and seasonal displays.
  • Historic Metropolis Area: Stroll through this charming area with its quaint streets, shops, and eateries.
  • Vibrant Downtown: Enjoy a lively atmosphere with local boutiques and cafes, perfect for a family outing.
  • Outdoor Activities: Explore urban parks that offer recreational opportunities for the whole family.

Top attractions near Oak Park

Oak Park, Illinois, is a fantastic spot for a family adventure or an outdoor city escape. With its charming urban parks, historic sites, and the lovely Oak Park Conservatory, there’s plenty to explore. Enjoy the vibrant culture and family-friendly experiences, as well as the beautiful central park. It's an ideal destination for those seeking a blend of relaxation and exploration.

  • Garfield Park Conservatory: A stunning conservatory garden just 4.8km from Oak Park, offering a lush, family-friendly environment with diverse plant collections and outdoor vibes that invite exploration and relaxation.
  • Project Room: An 12.9km journey will take you to this vibrant gallery showcasing contemporary art and fostering a cultural atmosphere that sparks creativity and conversation.
  • Willis Tower: This iconic skyscraper, located 12.9km away, boasts breathtaking city views from its observation deck, immersing you in the bustling urban landscape of Chicago.

Things to do recommended for couples

For a romantic getaway in Oak Park, enjoy a night of music at the Aragon Ballroom, savour a meal at the Historic Michael Jordan Restaurant, or unwind at Lynfred Winery for a delightful tasting experience. Each spot offers a unique vibe perfect for couples.

Things to do recommended for families

Families will love visiting Wrigley Field and Soldier Field for an exciting sports atmosphere, just a short drive from Oak Park. For a fun-filled adventure, head to Galloping Ghost arcade, where everyone can enjoy games and family-friendly vibes.

Things to do recommended for groups

Experience shopping at the Fashion Outlets of Chicago, only 12.9km from Oak Park, before catching a show at the Madison Street Theatre, right in town. For a fun night, head to Second City for some laughs, also a short drive away. Perfect for a group outing.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're heading off with a group, your family, or even your pets, or if you're planning an extended stay, be sure to apply the right filters to meet your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Oak Park with a group: Think about how many bedrooms you require, as well as any amenities like a full kitchen or outdoor area for group gatherings. The great news is that you can easily filter for all these options, and many more, on Vrbo.
  • Traveling to Oak Park with young kids: Traveling with little ones can be quite a task. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Oak Park: For many families, a holiday wouldn’t be the same without their furry companion. If you can relate, take a look at Vrbo properties that welcome pets. Most of these pet-friendly options come with feeding bowls and comfy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Oak Park: If you're on the hunt for holiday rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider including features like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Oak Park

Oak Park, Illinois, offers a delightful blend of family-friendly experiences and urban charm. Explore the vibrant downtown Oak Park, where you can enjoy local shops and eateries. Don't miss the historic Metropolis area, perfect for a leisurely stroll. Nearby, you'll find friendly communities that enhance the welcoming atmosphere. Whether you're seeking outdoor activities or cultural experiences, Oak Park and its surroundings provide a memorable vacation for the whole family.

  • North Riverside: Situated a mere 6.4km from Oak Park, North Riverside is a vibrant city known for its family-friendly atmosphere and outdoor adventures. Visitors flock to the North Riverside Park Mall, an expansive shopping centre that offers a variety of retail options and dining experiences. Outdoor enthusiasts will appreciate the nearby recreation parks, perfect for picnics and leisure activities. The city is also home to notable landmarks, including an urban park and a local stadium, providing ample opportunities for entertainment and relaxation.
  • Northwest Side: Also located 6.4km from Oak Park, the Northwest Side is a charming area that appeals to families and couples seeking a romantic getaway. This neighbourhood features lovely esplanades, ideal for leisurely strolls and enjoying the scenery. With its blend of residential charm and local amenities, Northwest Side offers a peaceful escape while remaining close to the urban conveniences of Chicago.
  • Logan Square: Just 8.0km from Oak Park, Logan Square is a bustling neighbourhood that perfectly combines family fun with city-themed experiences. Known for its lively recreation parks and vibrant music concert scene, this area is a hub of activity. Logan Square also boasts impressive landmarks, including stadiums and sports facilities, making it a great destination for sports enthusiasts. The neighbourhood's parks offer a perfect setting for families to enjoy outdoor activities and community events.

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.

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

Booking with Vrbo is a breeze

Are you keen to save some dollars on your upcoming trip? Think about being a bit flexible with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental. We're here to help you find the best options for your getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers an easy-to-use platform where you can plan new trips, continue from where you last stopped, or manage your travel arrangements. You can easily find your saved or booked properties sorted into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply head over to: https://www.bookabach.co.nz/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)
  • Dave & Buster's (7.9 mi / 12.7 km)
  • Lincoln Park Zoo (8.1 mi / 13.1 km)
  • Pirates Cove Childrens Theme Park (14.3 mi / 23.1 km)
  • The Glen Club (14.4 mi / 23.2 km)
  • LEGOLAND® Discovery Center (16.7 mi / 26.9 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 home accommodation in Oak Park?
Apartments are the most popular style of holiday home in Oak Park, according to our data. Even if you have a different vision in mind, Bookabach 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 home in Oak Park?
Several things determine what you'll pay for your holiday home 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 home. Put in your Oak Park travel dates to see all your options on Bookabach. Can't live without a private pool? Use the filters to pick the features and amenities you need.
Are there pet-friendly holiday homes in Oak Park?
Yes. There are. You can pick from 52 holiday homes that allow pets in Oak Park. Many of our pet-friendly holiday homes 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 Bookabach.
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 Bookabach, and then spend your downtime splish-splashing around in a swimming pool that's all your own.
What are popular home amenities in Oak Park?
A garden, a nearby river and a firepit head the list of most popular home amenities in Oak Park. Whether you're planning to travel as a party of one, with your significant other or a bunch of friends, Bookabach will help you find a holiday home that suits your tastes with all the features you need.
Are there large group holiday homes 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, Bookabach can help you find a large group home to suit the occasion.
Are there holiday homes in Oak Park that welcome kids?
With 51 family-friendly holiday homes 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 homes in Oak Park?
Yes, you can take your pick from 15 one-bedroom homes 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 homes in Oak Park?
Gather your nearest and dearest and enjoy a relaxing escape in one of the 18 two-bedroom holiday homes Oak Park has to offer.
Are there holiday homes 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 Bookabach and stay connected on your holiday.
How can I find holiday homes 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 home in Oak Park?
The minimum age is usually 16, 18 or 21. It can differ from one property to another on Bookabach, so check the rules of your preferred Oak Park stay before booking your trip.
How long can I rent a holiday home 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 homes may also offer weekly or monthly discounts, so you can stay longer for less money.

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