Discover a selection of 1,500 vacation rentals in Oak Park, IL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $127 per night, and condos and houses are popular options for a stay in Oak Park. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Oak Park
Destination guide

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.

Things to do

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.


Oak Park’s buzzing arts scene

Oak Park has a lively bar and restaurant scene, with many independent eateries, family-friendly restaurants, and quirky pubs. Head to Harrison Street, between Austin and Ridgeland Avenues, to discover boutique art galleries, independent shops, and buzzing nightlife. The local theaters are well worth investigating, especially the 76-year-old Lake Theatre, a vintage movie theater that screens arthouse and documentary flicks. From your Oak Park vacation rental, you can be in the heart of downtown Chicago in less than 30 minutes – putting the Skydeck at Willis Tower, and other Chicago landmarks like Grant Park, the Art Institute of Chicago, Shedd Aquarium, Adler Planetarium, and the shops and restaurants of Michigan Avenue all within easy sightseeing distance.


Oak Park through the seasons

Oak Park enjoys warm summers and cold winters – meaning you can enjoy sunny days in the local parks or out sailing on Lake Michigan in the summer months, and atmospheric snowy scenes during the winter months. May through September, temperatures hover pleasantly around the 70s, although can tip into the 100s in the height of July and August. These are the months to head to Oak Park’s Austin Gardens for a picnic, to enjoy the wildflowers, or catch some outdoor theater.

Natural features

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.

How to get there

Transportation options to and around Oak Park

Fly into Chicago, IL (MDW-Midway Intl.), the closest airport, located 7.3 mi (11.7 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Chicago, IL (ORD-O'Hare Intl.), which is 8.6 mi (13.8 km) away.

If you'd rather travel by train, the main station serving the city is Oak Park Station. You can see more of Oak Park by catching a ride on the metro at Oak Park Station, Ridgeland Station or Harlem-Lake Station.

How many vacation rentals are available around Oak Park, IL?

Our 2021 property listings offer a large selection of 1,258 vacation rentals around Oak Park. From 1,000 condo and apartment rentals to 205 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Oak Park?

Vrbo offers a large selection of vacation rentals near lovely places in Oak Park. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Oak Park Visitors Center: 1,594 vacation rentals
  • Frank Lloyd Wright Home and Studio: 1,578 vacation rentals
  • Ernest Hemingway Museum and House: 1,585 vacation rentals
  • Moore House: 1,582 vacation rentals
  • Oak Park Station: 1,586 vacation rentals

But there are many other points of interest around Oak Park listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Condos/Apartments in Oak Park?

Yes, of course. Vrbo has 1,000 Condos/Apartments in Oak Park. Our other popular types of vacation rentals in Oak Park include:

  • Houses: 205 rentals available
  • Townhouses: 16 rentals available
  • Studios: 834 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Cottages and more.

Can I find a vacation rental with pool in Oak Park?

Yes, you can select your preferred vacation rental with pool among our 189 vacation rentals with pool available in Oak Park. Please use our search bar to access the selection of vacation rentals available.