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.

Can I find a vacation rental around Oak Park?

Yes, our 2019 property listings offer a large selection of 1,498 vacation rentals near Oak Park. From 195 Houses to 1,241 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Oak Park for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Oak Park?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Oak Park:

  • Chicago Loop: 760 vacation rentals
  • Wrigleyville: 411 vacation rentals
  • Lincoln Park: 671 vacation rentals
  • River North: 500 vacation rentals
  • Magnificent Mile: 552 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

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

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

  • Frank Lloyd Wright Home and Studio: 1,731 vacation rentals
  • Ernest Hemingway Museum and House: 1,730 vacation rentals
  • Oak Park Station: 1,732 vacation rentals
  • Madison Street Theatre: 1,725 vacation rentals
  • Unity Temple: 1,703 vacation rentals

But there are many other points of interest around Oak Park listed on HomeAway 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 Houses in Oak Park?

Yes, of course. HomeAway has 195 Houses in Oak Park. Our other popular types of vacation rentals in Oak Park include:

  • Condos/Apartments: 1,241 rentals available
  • Cottages: 4 rentals available
  • Townhouses: 19 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows 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 147 vacation rentals with pool available in Oak Park. Please use our search bar to access the selection of vacation rentals available.

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