Where to stay around Oak Park, IL?

Our 2019 property listings offer a large selection of 1,791 vacation rentals near Oak Park. From 808 Hotels to 789 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 VRBO.

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:

  • Lakeview: 301 vacation rentals
  • Chicago Loop: 704 vacation rentals
  • Streeterville: 203 vacation rentals
  • Old Town: 236 vacation rentals
  • Wrigleyville: 326 vacation rentals

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

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:

  • Frank Lloyd Wright Home and Studio: 2,565 vacation rentals
  • Ernest Hemingway Museum and House: 2,584 vacation rentals
  • Madison Street Theatre: 2,533 vacation rentals
  • Unity Temple: 2,565 vacation rentals
  • Oak Park Station: 2,560 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 Hotels in Oak Park?

Yes, of course. VRBO has 808 Hotels in Oak Park. Our other popular types of vacation rentals in Oak Park include:

  • Condos/Apartments: 789 rentals available
  • Studios: 635 rentals available
  • Houses: 141 rentals available

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

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

Yes, you can select your prefered vacation rental with pool among our 461 vacation rentals with pool available in Oak Park. Please use our search bar to access the selection of vacation rentals available.

    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 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’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 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.

    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.