Oak Park vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.
1 of 3 pages
1 of 3 pages

Popular amenities for Oak Park vacation rentals

Stay near Oak Park's top sights

Frank Lloyd Wright Home and Studio184 locals recommend
Downtown Oak Park9 locals recommend
Jewel-Osco13 locals recommend
Trader Joe's52 locals recommend
Classic Cinemas Lake Theatre72 locals recommend
West Suburban Medical Center6 locals recommend

Quick stats about vacation rentals in Oak Park

  • Total rentals

    310 properties

  • Total number of reviews

    16K reviews

  • Family-friendly rentals

    150 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wifi availability

    310 properties include access to wifi

Frequently Asked Questions

  • How is the weather in Oak Park?

    Oak Park experiences a mix of all four seasons. Summers can be warm, often reaching up to 85°F (29°C), while winters can be chilly, with temperatures often dropping to 20°F (-6°C) and sometimes lower. Spring and autumn are milder and are often considered comfortable for exploring outdoors.

  • What are some of the best things to do in Oak Park?

    Visitors to Oak Park frequently explore the Frank Lloyd Wright Home and Studio, admire the unique architecture in the Historic District, or discover the life of Ernest Hemingway at the Hemingway Birthplace Home. The Oak Park Farmers' Market is also a popular spot, especially on weekends.

  • What is the best time of year to visit Oak Park?

    The most frequented time to visit Oak Park is during the summer and fall seasons. Popular local events include 'A Day in our Village' festival in June, and the 'Oaktoberfest' which celebrates the arrival of fall in September.

  • What are the best places to stay in Oak Park?

    In Oak Park, the Downtown area is often recommended for its proximity to local attractions, restaurants, and shops. The Frank Lloyd Wright Historic District is another attractive area, particularly for architecture enthusiasts.

  • What are the best places to visit in Oak Park?

    Places often frequented in Oak Park include the Frank Lloyd Wright Home and Studio, the Ernest Hemingway Birthplace Home, and the Oak Park Conservatory. The Pleasant Home and Unity Temple are also worth exploring for their architectural significance.

  • What are some hiking trails in Oak Park?

    Though largely an urban area, Oak Park is near several trails. The Des Plaines River Trail, just 15 miles (24 km) away, winds through various ecosystems. Closer to town, the Oak Park River Forest provides softer trails for a leisurely stroll.

  • What are some family activities to do in Oak Park?

    Families in Oak Park often enjoy exploring the Wonder Works Children's Museum, picnicking in one of the local parks, or participating in one of the programs at the Oak Park Public Library. The Oak Park Conservatory is also a hit with children of all ages.

  • What are some of the best day trip ideas in Oak Park?

    Day trips from Oak Park often include a visit to Chicago, just 9 miles (14 km) away, to explore landmarks like the Art Institute, Navy Pier, and Millennium Park. A trip to the Brookfield Zoo, 6 miles (10 km) away, is also a popular choice for families.

  • Are there pet-friendly vacation rentals in Oak Park?

    Four-legged friends are welcome in Oak Park. Choose from more than 70 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Oak Park?

    Yes! Work meets play with ease at over 170 vacation rentals in Oak Park featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Oak Park