Oak Park vacation rentals

We found 2,719 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Discover a selection of 23 homes, 57 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.

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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 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.

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.

Transportation options to and around Oak Park

Fly into Chicago O'Hare Intl. Airport (ORD), the closest airport, located 8.9 mi (14.4 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Chicago Midway Airport (MDW), which is 7 mi (11.3 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 most popular type of vacation rental accommodation in Oak Park?

Apartments are the most popular style of vacation rental in Oak Park, according to our data. Even if you have a different vision in mind, Vrbo has properties in loads of sizes and shapes. Look through our options to find your perfect match.

How much does it cost to rent a vacation rental in Oak Park?

Several things determine what you'll pay for your vacation rental in Oak Park, including the type of property, season and length of stay. However, all of our vacation homes have one thing in common — amazing value. Simply enter your travel dates to find your ideal match.

How much does it cost to rent a beach house in Oak Park?

When you travel and the size and style of the property will influence the cost of your beachside vacation rental. Put in your Oak Park travel dates to see all your options on Vrbo. Can't live without a private pool? Use the filters to pick the features and amenities you need.

Are there pet-friendly vacation rentals in Oak Park?

Yes. There are. You can pick from 52 vacation rentals that allow pets in Oak Park. Many of our pet-friendly vacation rentals even come with a garden for your fur child to run around in, special dog beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your pawfect place on Vrbo.

Can I rent a house with a pool in Oak Park?

Add a new level of fun to your getaway by booking one of the four houses with a private pool in Oak Park. Use our handy search filter to find the kind of property you want on Vrbo, and then spend your downtime splish-splashing around in a swimming pool that's all your own.

What are popular rental amenities in Oak Park?

A garden, a nearby river and a firepit head the list of most popular rental amenities in Oak Park. Whether you're planning to travel as a party of one, with your significant other or a bunch of friends, Vrbo will help you find a vacation rental that suits your tastes with all the features you need.

Are there large group vacation rentals in Oak Park?

With two properties that can host 10 guests or more in Oak Park, you won't have to keep anyone off the invite list. From vacations with the extended family to special events like anniversary parties and weddings, Vrbo can help you find a large group rental to suit the occasion.

Are there vacation rentals in Oak Park that welcome kids?

With 51 family-friendly vacation rentals available in Oak Park, now is the perfect time to introduce your children to the wonders of travel. Simply click on our "Properties good for families" filter box to search for stays that feature amenities ideal for vacationing families, like multiple bedrooms, patios, bunk beds and hot tubs.

What are the top attractions for families in Oak Park?

Keeping the kids entertained during your Oak Park vacation is a snap with these cool family-friendly attractions:

  • Chicago Riverwalk
  • Shedd Aquarium
  • Field Museum of Natural History

Are there one-bedroom vacation rentals in Oak Park?

Yes, you can take your pick from 15 one-bedroom rentals in Oak Park. Whether you're on the lookout for a secluded cottage or an upmarket condo, our one-bedroom properties are just right if you don't require loads of space. One of the best parts about having your own pad? You won't need to share your adventure with strangers.

Can I find two-bedroom vacation rentals in Oak Park?

Gather your nearest and dearest and enjoy a relaxing escape in one of the 18 two-bedroom vacation rentals Oak Park has to offer.

Are there vacation rentals with WiFi in Oak Park?

Whether you'd like to keep up with the news, make a video call or surf your social networks, there are 16 vacation homes with WiFi in Oak Park. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.

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