Oak Park vacation rentals

We found 2,904 vacation rentals — enter your dates for availability

Discover a selection of 30 homes, 63 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.

Vacation rentals with weekly discounts - Oak Park

Showing deals for:May 22 - May 29

Image gallery for Enamored in Elmhurst

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

Enamored in Elmhurst

Elmhurst

13% off
Price is $479
$3,351 for 7 nights
All fees included
Enamored in Elmhurst

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Oak Park

Why visit Oak Park

  • Family-friendly activities: Oak Park offers a variety of attractions perfect for visitors of all ages.
  • Scenic parks: Enjoy beautiful green spaces and local parks that enhance the outdoor experience.
  • Cultural experiences: Engage with local churches and historical sites that reflect the area's rich heritage.
  • Charming nearby communities: Explore the inviting atmosphere of neighboring Forest Park filled with history.
  • Diverse accommodation options: Find cozy apartments, spacious condos, and charming house rentals for every budget.

Popular types of accommodation in Oak Park

Planning a getaway to Oak Park? You're in for a treat. Discover a variety of vacation rentals in Oak Park, including cozy apartments, houses, and spacious condos. Whether you're seeking affordable rentals or charming house rentals, our platform offers transparency and reassurance to help you find the perfect Oak Park apartment home for your stay. Explore your options and enjoy a memorable trip.

  • Apartments: The top choice for visitors in Oak Park, offering comfortable living spaces with all the amenities for a convenient stay.
  • Houses: A great option for families and groups, providing spacious accommodations and a home-like atmosphere.
  • Condos: These stylish units are perfect for those seeking modern living with shared amenities in a community setting.
  • Cottages: Cozy and charming, cottages offer a quaint retreat for a peaceful getaway in Oak Park.**

Top attractions near Oak Park

Oak Park, Illinois, is a fantastic destination for family-friendly vacations, offering a vibrant mix of outdoor activities and city experiences. Visitors can explore urban parks, attend events at conference venues, or visit local churches. The area's attractions provide a rich cultural experience, making it an excellent choice for travelers seeking both relaxation and adventure. Whether you're traveling solo or with loved ones, Oak Park has something for everyone to enjoy.

  • Willis Tower: Standing tall at 1,450 feet, this iconic skyscraper offers breathtaking views of the Chicago skyline from its Skydeck. Experience the thrill of stepping onto the glass ledge that extends out over the city, providing a unique perspective of urban life below.
  • Merchandise Mart: A historic hub for commerce, this impressive building is known for its stunning Art Deco architecture. Explore its vast showrooms and enjoy cultural events that showcase design and innovation, making it a center for creativity.
  • Donald E. Stephens Convention Center: This expansive venue hosts a variety of events, from trade shows to conferences. Its modern facilities and convenient location make it a vital part of Chicago’s business landscape, catering to professionals and visitors alike.

Things to do recommended for couples

For a romantic getaway in Oak Park, enjoy live music at the Aragon Ballroom, savor a meal at the Historic Michael Jordan Restaurant, or indulge in wine tasting at Lynfred Winery. Each spot offers a unique atmosphere to make your couple's vacation memorable.

Things to do recommended for families

Your family will love visiting Wrigley Field, just 8 miles away, for an exciting sports experience. Enjoy adventure at Galloping Ghost, 6 miles away, or explore the wonders of the universe at the Cernan Earth and Space Center, located 4 miles from Oak Park.

Things to do recommended for groups

Groups visiting Oak Park can shop at the Fashion Outlets of Chicago for a lively experience, enjoy a performance at the Madison Street Theatre for a taste of local culture, and share laughs at Second City, all while immersing themselves in the vibrant community atmosphere.

*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

When planning your trip—whether you're traveling with friends, family, pets, or seeking extended stays—be sure to prioritize your preferences when filtering your options. Here are some helpful tips for booking on Vrbo.

  • Traveling to Oak Park with a group: Think about how many bedrooms you’ll require, along with features like a fully-equipped kitchen or outdoor areas for group activities. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Oak Park with young kids: Traveling with little ones can present its own set of challenges. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Oak Park: For many, a family vacation isn’t truly fulfilling without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly rentals offer feeding bowls and beds, ensuring that your entire family feels comfortable and at home.
  • Planning for a long term stay visiting Oak Park: If you're in search of vacation rentals with discounts 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 include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Oak Park

Oak Park, Illinois, offers a delightful blend of family-friendly activities and scenic outdoor spaces. Explore the charming local parks and beautiful green areas that make this city a perfect vacation spot. Just a short distance away, Forest Park provides an inviting atmosphere filled with friendly people and rich history. Whether you're seeking urban adventures or tranquil retreats, Oak Park and its neighboring communities promise an unforgettable experience for every traveler.

  • Chicago: As a bustling metropolis, Chicago is renowned for its vibrant culture, stunning architecture, and rich history. Located adjacent to Oak Park, the city offers a plethora of experiences for every traveler. From family-friendly attractions like the Shedd Aquarium and the Field Museum to outdoor spaces such as Millennium Park, there’s no shortage of activities. Sports fans can catch a game at Wrigley Field or the United Center, while shoppers can explore the Magnificent Mile for an unforgettable retail experience. The city's diverse neighborhoods are also home to amazing dining options, live music, and art galleries, making Chicago a must-visit destination.
  • South Austin: Situated just a mile from Oak Park, South Austin is a charming neighborhood known for its quirky atmosphere and artistic vibe. This area is perfect for families seeking outdoor adventures, with parks like the scenic South Austin Park offering plenty of recreational activities. Music lovers will appreciate the local concert scene, highlighting the area’s vibrant arts culture. Additionally, the neighborhood hosts various educational establishments, making it a great place to learn and explore. With its welcoming community and eclectic mix of attractions, South Austin is a delightful spot to experience.
  • Austin: Also located a mile away from Oak Park, Austin boasts a unique blend of urban and outdoor experiences. Families can enjoy fun activities at local recreation parks, while theater enthusiasts can catch a show at one of the many venues throughout the area. The neighborhood is known for its lively cultural scene, featuring music festivals and art events. With its lush urban parks and sports facilities, Austin invites visitors to relax and engage with nature while discovering local history and charm. This vibrant community is a fantastic addition to your travel itinerary.

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 a breeze

Are you eager to save on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and vacation rental type. We're here to help you find the perfect getaway.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash on the total booking amount. It truly benefits you to be the trip organizer. Become a member of our One Key rewards program to unlock exclusive savings and accumulate OneKeyCash on eligible stays. Sign up now and begin earning.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform for planning your travels. You can create new trips, resume your previous work, or organize your travel plans all in one place. You'll find your saved or booked properties neatly arranged under categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

On the doorstep of Chicago

The village of Oak Park borders the West Side of Chicago, sitting between West North Avenue and West Roosevelt Road. A convenient base for seeing the sights of Chicago, this residential neighborhood has attracted some illustrious residents over the years, including Ernest Hemingway and Frank Lloyd Wright. Today, an Oak Park vacation rental offers an historic setting and a relaxed, family-friendly vibe where you can enjoy great shopping, dining, and a vibrant arts and cultural scene just a few miles from bright lines of Chicago and the picturesque shores of Lake Michigan.

Oak Park’s famous former residents

Celebrated architect Frank Lloyd Wright and his wife settled in Oak Park in 1889 and, as a result, Oak Park boasts the world's largest collection of Frank Lloyd Wright architecture – including his home and studio, and the game-changing Modernist splendor of the Unity Temple. An easy 4-block Frank Lloyd Wright walk will take you past several residences designed by the master architect and is a highlight of any Oak Park itinerary. History buffs will also love the Hemingway birthplace and Hemingway Museum in Oak Park, which offer a fascinating insight into the life of the iconic author.

Head outdoors in Oak Park

Oak Park is a bicycle-friendly community, and you can explore miles of biking routes from your Oak Park vacation rental. The Grand Illinois Trail cuts through Oak Park along Augusta Boulevard – connecting you with an epic loop trail from Lake Michigan to the Mississippi and back. The Illinois Prairie Path, a network of 61 miles of former railroad, is also easily accessible. Chicago’s beautiful green spaces of Lincoln Park and Grant Park are within reach, offering beautiful lakeside vistas across the twinkling waters of Lake Michigan. Relax on their beaches and tree-lined lawns or head out onto the lake itself.

Transportation options to and around Oak Park

Fly into Chicago O'Hare Intl. Airport (ORD), the closest airport, located 8.9 mi (14.4 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Chicago Midway Airport (MDW), which is 7 mi (11.3 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 best area to stay in Oak Park, Illinois, United States of America when booking a vacation rental?
One of the best areas to consider for a vacation rental in Oak Park, Illinois, is the Historic District. This charming neighborhood is known for its stunning architecture, with many homes designed by the famous architect Frank Lloyd Wright, making it a visual delight for visitors. Staying here puts you within walking distance of attractions like the Frank Lloyd Wright Home and Studio, where you can immerse yourself in the history of American architecture. Additionally, the nearby Oak Park Art League offers a glimpse into the local artistic community and hosts various exhibitions and classes.

Another great option is the area around the Oak Park Avenue corridor, which features a vibrant mix of shops, cafes, and restaurants. This neighborhood is lively and convenient, providing easy access to the Green Line train, making it simple to explore nearby Chicago. Here, you can also enjoy a visit to the beautiful Scoville Park, which often hosts community events and serves as a lovely spot for relaxation.
How much does it cost to rent a vacation home in Oak Park?
Prices for vacation 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 vacation 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 vacation rental accomodation in Oak Park?
In Oak Park, apartments are the most popular vacation rental option, with around 55 available throughout the area. These apartments are typically situated in charming neighborhoods close to attractions such as the Frank Lloyd Wright Home and Studio and the Ernest Hemingway Birthplace Museum. Travelers can expect amenities like fully equipped kitchens, cozy living areas, and often laundry facilities, making them ideal for both short and extended stays.

Additionally, there are about 27 vacation houses available, providing more space for families or larger groups. These homes often feature multiple bedrooms, private yards, and outdoor seating areas, great for enjoying the local atmosphere. There are also several cottages and condos that offer a unique and comfortable lodging experience, suiting different preferences.
Are there any family house rentals in Oak Park?
In Oak Park, Illinois, there are numerous family-friendly house rentals available, with around 56 options to choose from. The area is known for its beautiful architecture, including homes designed by Frank Lloyd Wright, making it a captivating place for families to explore. Many of these properties feature spacious living rooms, fully equipped kitchens, and outdoor areas great for children to play. Visitors can also find amenities like Wi-Fi and laundry facilities, ensuring a comfortable stay.

Families will appreciate the proximity to local parks, such as Scoville Park, where playgrounds and picnic spots are available. Additionally, the vibrant downtown area offers various dining options and shops, enhancing the overall experience.
Can I rent a vacation home with a pool or hot tub in Oak Park?
In Oak Park, there are several vacation homes available for rent that feature pools and hot tubs, making it a great choice for travelers seeking relaxation and leisure. This charming suburb of Chicago is known for its historic architecture and proximity to downtown Chicago, providing a blend of urban and residential experiences. Many of the vacation rentals in Oak Park come equipped with amenities such as private pools, hot tubs, spacious outdoor areas for lounging, and fully equipped kitchens, allowing for comfort and convenience during your stay. Additionally, some properties may include outdoor dining spaces, superb for enjoying meals al fresco.
Can I find long-stay vacation rentals in Oak Park?
A long-stay vacation rental in Oak Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Oak Park?
In Oak Park, travelers can find a variety of pet-friendly house rentals, with around 31 options available to choose from. This charming suburb, known for its historic architecture and vibrant community, offers an array of amenities in its vacation homes. Expect to find properties featuring modern kitchens, spacious living areas, and outdoor spaces like patios or gardens, which are great for families and pet owners alike.

Oak Park is also conveniently located near several parks, such as Scoville Park and Austin Gardens, where pets can enjoy leisurely walks and playtime. Additionally, the area boasts pet-friendly cafes and shops, making it a delightful destination for those traveling with furry companions. See all pet-friendly rentals in Oak Park.
Are there any remote work vacation rentals in Oak Park?
In Oak Park, Illinois, there are numerous remote work vacation rentals available, with around 79 options to choose from. This suburban community, known for its historic architecture and vibrant arts scene, offers various properties that cater well to remote workers. Travelers can expect amenities such as high-speed internet, complimentary Wi-Fi, and dedicated workspaces equipped with desks and comfortable chairs, making it easy to stay productive while enjoying the comforts of home.

The area is also close to cultural attractions like the Frank Lloyd Wright Home and Studio, as well as the Oak Park Art League, providing opportunities for leisure during breaks. The local dining scene and proximity to parks further enhance the appeal for those seeking a balance between work and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oak Park vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Oak Park with parking available—perfect for families or travelers 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, travelers can expect a variety of popular vacation rental amenities that enhance their stay. Most rentals feature a fully equipped kitchen, allowing guests to prepare their own meals conveniently. Onsite parking is commonly available, making it easy for visitors to explore the area without worrying about street parking. Many properties include a coffee and tea maker, great for enjoying a warm beverage at any time of day. Additionally, a dedicated desk space is often provided, suiting those who may need to work during their visit. Many rentals also boast a deck or patio, offering a lovely outdoor space to relax and enjoy the pleasant Oak Park atmosphere.
When is the best time to visit Oak Park for a vacation rental?
The best time to visit Oak Park for a vacation rental is during the vibrant summer months of May through July, with July being particularly popular among travelers. This period draws families and tourists eager to explore the area's rich architectural heritage, including the famed Frank Lloyd Wright Home and Studio. The warm temperatures, typically ranging from the mid-60s to mid-80s Fahrenheit, create an inclusive setting for outdoor sightseeing and leisurely strolls through the picturesque parks and historic districts.

As you wander through Oak Park, you'll find a variety of outdoor activities available, from enjoying live performances at local parks to indulging in the delicious offerings at seasonal farmers' markets. The lively ambiance during peak season makes it a great time to connect with fellow travelers and immerse yourself in the local culture.

For those seeking a more budget-friendly option, consider visiting in November. This month offers a quieter experience, allowing you to appreciate the charm of Oak Park without the bustling crowds. You'll also have the opportunity to enjoy the area's beautiful autumn colors, creating a picturesque backdrop for your visit.
How early should I book a Oak Park vacation rental?
Book your Oak Park vacation 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 vacation 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, Illinois, United States of America?
In Oak Park, visitors can explore a rich array of attractions that highlight both its historical significance and vibrant community. The Frank Lloyd Wright Home and Studio is a major draw, offering guided tours of the famed architect's residence and the birthplace of his unique design philosophy. Nearby, the Unity Temple, another of Wright's masterpieces, showcases stunning architectural features and serves as an important cultural landmark.

The Oak Park Conservatory provides a beautiful indoor garden experience, featuring a variety of plant species and seasonal displays, making it a lovely spot for nature enthusiasts. For those interested in literature, the Ernest Hemingway Museum celebrates the life and works of the famous author, who was born here, and offers insights into his early influences.

The area around Oak Park's downtown is bustling with shops, cafes, and restaurants, making it a great place for dining and leisure.
Can I change or cancel my Oak Park home rental booking on Vrbo?
To find Oak Park vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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.

More Vacation Ideas