Oak Park vacation rentals

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Discover a selection of 34 homes, 52 apartments, and other vacation rentals in Oak Park that are perfect for your trip. Whether you’re staying in a vacation home with your kids or with friends, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and garden. Whatever you're looking for, you'll find a rental for everyone's needs, including accessible or non-smoking choices.
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  • All the privacy of home
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Find out more about Oak Park

Find out more about Oak Park

Why visit Oak Park

  1. Rich Artistic Heritage: Oak Park is renowned for its vibrant arts scene, featuring unique galleries and cultural events.
  2. Historic Architecture: Discover beautiful historic buildings, including the Frank Lloyd Wright Home and Studio.
  3. Family-Friendly Activities: Enjoy a variety of parks and outdoor spaces suitable for families and kids.
  4. Charming Neighbourhoods: Explore nearby Forest Park with its local businesses and community events.
  5. Comfortable Accommodations: Experience a range of vacation rentals, from cozy apartments to spacious homes.

Popular types of accommodation in Oak Park

Discover the charm of Oak Park with our diverse selection of vacation rentals. Whether you're seeking a cozy apartment, a spacious private vacation home, or a stylish condo, we have options to suit every traveller’s needs. Enjoy affordable rentals and the comfort of Oak Park apartment homes, including the popular Oakridge house for rent. Your perfect getaway awaits in this delightful community!

  • Apartments: The top choice for visitors, offering a comfortable and convenient stay in Oak Park, perfect for solo travellers or couples.
  • Houses: A popular option for families or groups, providing ample space and a home-like atmosphere.
  • Condos: Ideal for those seeking modern amenities and often located near attractions.
  • Cottages: Quaint and charming, perfect for a cozy retreat in a picturesque setting.
  • Cabins: A rustic option for nature lovers, offering a peaceful getaway.**

Top attractions in Oak Park

Oak Park, Illinois, offers a delightful mix of family-friendly activities and cultural exploration, making it perfect for a diverse vacation. Visitors can enjoy beautiful urban parks, historic buildings, and event venues that showcase the city's rich history and vibrant community. With something for everyone, from outdoor adventures to engaging city experiences, Oak Park is an ideal destination for Canadian tourists seeking memorable moments.

  1. Willis Tower: A towering icon of Chicago, this skyscraper offers breathtaking views from its observation deck. Experience the vibrant city atmosphere and explore the surrounding area filled with shops and restaurants.
  2. Donald E. Stephens Convention Center: A hub for business and events, this venue hosts a variety of conferences and expos. Immerse yourself in the professional vibes and enjoy the modern facilities.
  3. University of Illinois Chicago: A historic institution with beautiful architecture, UIC showcases rich cultural heritage and offers a glimpse into student life, art, and community events.

Things to do recommended for couples

For a romantic getaway in Oak Park, enjoy a lively concert at Aragon Ballroom, savour a meal at the historic Michael Jordan Restaurant, and unwind with exquisite wines at Lynfred Winery. Each offers a unique charm, perfect for couples seeking memorable experiences together.

Things to do recommended for families

Families will love exploring Wrigley Field for a sports experience, visiting Galloping Ghost for arcade adventures, and enjoying the Cernan Earth and Space Center for an entertaining planetarium visit—all conveniently located within a short drive from Oak Park.

Things to do recommended for groups

Experience the vibrant culture at Rosemont Theatre, enjoy shopping at the Fashion Outlets of Chicago, and share laughs at Second City. These activities, all within 12.9km of Oak Park, promise unforgettable moments for your group getaway!

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

When you’re planning a trip—whether you're going with a group, as a family, bringing along your pets, or seeking extended stays—it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Oak Park with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Oak Park with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize 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 getaway isn’t truly enjoyable unless their furry companion is along for the adventure. If you relate to this, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Oak Park: If you're in search of vacation rentals offering 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 rental options. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay in Oak Park

Oak Park, Illinois, is a charming destination perfect for families and outdoor enthusiasts. Known for its rich artistic heritage and friendly atmosphere, the city offers a blend of urban vibrancy and tranquil parks. Explore the nearby neighbourhoods like Forest Park, where you can enjoy local businesses and community events. Don't miss the cultural experiences Oak Park has to offer, including unique art galleries and welcoming locals, making it an ideal spot for a memorable vacation.

  • South Austin: A vibrant neighbourhood located a mile from Oak Park, South Austin beckons visitors with its family-friendly atmosphere and outdoor experiences. Known for its recreational parks, this area offers a plethora of activities, from enjoying music concerts to educational outings. Local landmarks like the sports facility stadium and urban parks provide ample opportunities for outdoor enjoyment, making it a perfect spot for families and those seeking a lively city experience.
  • Austin: Also situated a mile from Oak Park, Austin is a dynamic neighbourhood that combines an urban vibe with family-oriented activities. Visitors can immerse themselves in the local culture by exploring recreation parks and enjoying performances at theatres or the arena entertainment facility. The proximity to urban parks and sports facility stadiums enhances the appeal, providing a mix of relaxation and excitement for tourists looking to experience the city's vibrant lifestyle.
  • Forest Park: Located two miles from Oak Park, Forest Park is a charming city that offers a delightful blend of family-friendly attractions, outdoor adventures, and urban experiences. Visitors can engage in educational activities and enjoy entertainment at the arena facility while taking advantage of the lush recreation parks. The nearby sports facility stadium and urban parks serve as perfect backdrops for relaxation and leisure, making Forest Park an inviting destination for tourists of all ages.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 some money on your next getaway? Keeping your travel dates flexible can be a great strategy, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To help you find the perfect Vrbo property that fits your budget, be sure to use our filters to sort by price, location, and type of vacation rental. We're here to assist you in making the most of your travel experience!

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new adventures, pick up right where you paused, or manage your travel arrangements. You can easily find the properties you've saved and booked under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Oak Park getaway

The area's architecture and temples are just a few of the reasons to vacation in 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-sees in the area. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation 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

Do you want to find top things to see and do in the city? Venture out of your cozy vacation rental and check out everything that makes Oak Park a one-of-a-kind vacation spot. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Galloping Ghost (6 mi / 9.6 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)
  • The Glen Club (14.4 mi / 23.2 km)

Exploring the natural features in Oak Park

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Oak Park is a great spot to appreciate mother nature. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • 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)

Transportation options to and around Oak Park

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

If you're traveling by train, the main station is Oak Park Station. You can see more of 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 vacation rental accommodation in Oak Park?
Apartments are the most popular style of vacation 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 vacation rental in Oak Park?
Several things determine what you’ll pay for your vacation rental in Oak Park, including the type of property, season and length of stay. However, all of our vacation 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 vacation 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 vacation rentals in Oak Park?
Yes. There are. You can pick from 52 vacation rentals that allow pets in Oak Park. Many of our pet-friendly vacation 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 vacation rental that suits your tastes with all the features you need.
Are there large group vacation 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 vacations 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 vacation rentals in Oak Park that welcome kids?
With 51 family-friendly vacation 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 vacationing 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 vacation is a snap with these cool family-friendly attractions:

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

Are there one-bedroom vacation 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 vacation rentals in Oak Park?
Gather your nearest and dearest and enjoy a relaxing escape in one of the 18 two-bedroom vacation rentals Oak Park has to offer.
Are there vacation 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 vacation homes with WiFi in Oak Park. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Oak Park?
You’ll have your pick of 48 vacation 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 vacation 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 vacation rental in Oak Park for?
The amount of time you can book an Oak Park vacation 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 vacation rentals may also offer weekly or monthly discounts, so you can stay longer for less money.

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