Oak Park vacation rentals

We found 2,944 vacation rentals — enter your dates for availability

Discover a selection of 32 homes, 55 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:Nov 14 - Nov 21
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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)
  • 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 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 best area to stay in Oak Park when booking a vacation rental?
When considering a vacation rental in Oak Park, Illinois, a popular area to stay is the historic district, particularly around the Frank Lloyd Wright Home and Studio. This neighbourhood is rich in architectural heritage, showcasing a stunning array of buildings designed by the renowned architect himself. Staying here places you within walking distance of the Unity Temple, another masterpiece by Wright, as well as the charming shops and cafés along Oak Park Avenue.

Another appealing area is the vicinity of the Oak Park Conservatory, which offers a lovely respite with its beautiful gardens and plant collections. This neighbourhood allows you to enjoy a peaceful atmosphere while still being close to the vibrant local community. In both of these areas, you will find a variety of vacation rental options, ranging from quaint bungalows to spacious apartments, providing a comfortable base for your stay.
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 travelling 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.
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 type of vacation rental, with about 48 available across the area. These apartments are often situated in charming neighbourhoods close to top sites such as the Frank Lloyd Wright Home and Studio and the historic Unity Temple. Most rooms come equipped with modern amenities, including fully equipped kitchens, comfortable living areas, and laundry facilities, suiting both short and extended stays.
Are there any family house rentals in Oak Park?
In Oak Park, Illinois, there are numerous family-friendly house rentals, with around 60 available throughout the area. This charming suburb offers a variety of properties that cater to families, featuring spacious living areas, fully equipped kitchens, and convenient amenities such as Wi-Fi and laundry facilities. Many homes also include outdoor spaces like gardens or patios, great for children to play or for families to gather after a day of exploring.
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. 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, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these vacation homes feature amenities such as fully equipped kitchens, spacious living areas, and private outdoor spaces, allowing guests to enjoy comfort and convenience during their stay.

The neighbourhood is known for its beautiful architecture, with some rentals situated in historic districts that showcase stunning homes designed by Frank Lloyd Wright. The area is also close to several parks, such as Scoville Park and Austin Gardens, which offer ample green spaces for walking pets and enjoying the outdoors.
Are there any remote work vacation rentals in Oak Park?
In Oak Park, Illinois, there are numerous remote work vacation rentals available, with around 75 options to choose from. This vibrant suburb, known for its rich architectural history and proximity to Chicago, offers a variety of accommodations that cater to the needs of remote workers. Many properties come equipped with dedicated workspaces, including desks, ergonomic chairs, and high-speed Wi-Fi, ensuring a productive environment for those working from home. 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 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 rental amenities include fully equipped kitchens, which are a staple in many vacation rentals. These kitchens come complete with cookware, dishware, and utensils, allowing guests to prepare their own meals during their stay. Additionally, most properties feature modern appliances such as refrigerators, microwaves, and stovetops, ensuring convenience for travellers.
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 to July. This peak season attracts a diverse array of travellers, particularly those keen on exploring the area's rich architectural heritage, including the iconic works of Frank Lloyd Wright. The warm weather, with average temperatures reaching the high 20s Celsius, enhances the experience of outdoor activities such as walking tours and picnics in the lush parks.

July stands out as the most popular month, offering a lively atmosphere filled with local events, festivals, and cultural activities. Visitors can engage in Oak Park's unique charm while enjoying the convenience of nearby attractions in Chicago, just a short train ride away.

For those looking to save a bit, consider visiting in November. This month, while quieter, offers a chance to enjoy the beautiful autumn scenery and explore the area without the crowds. You can experience the stunning fall colours in the local parks, which create a picturesque backdrop for leisurely strolls.
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?
In Oak Park, visitors can discover a rich array of attractions, particularly known for its historical significance and architectural beauty. The Frank Lloyd Wright Home and Studio, located in the heart of the village, showcases the renowned architect's early works and offers guided tours to those interested in design. Nearby, the Unity Temple, also designed by Wright, is a UNESCO World Heritage site and exemplifies his innovative use of space and light.

The Oak Park Arts District is a vibrant area filled with galleries, studios, and shops, providing a creative atmosphere that is superb for leisurely exploration. Additionally, the Ernest Hemingway Birthplace Museum celebrates the famous author, offering insights into his early life and influences.
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 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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