Oak Park vacation rentals

We found 2,697 vacation rentals — enter your dates for availability

Discover a selection of 36 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 kind of vacation rental in Oak Park, according to our data. Even if you have something a little different in mind, Vrbo has vacation homes in a variety of sizes and shapes. Look through our options to find your ideal match.
How much does it cost to rent a vacation rental in Oak Park?
Several things can determine what you’ll pay for a vacation rental in Oak Park, including the season, type of property and length of stay. Still, all Vrbo homes have one thing in common — exceptional value. Simply enter your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Oak Park?
Prices for beach houses in Oak Park can differ depending on the style and size of the property and when you’re traveling. Simply enter your travel dates into Vrbo and how many guests to view vacation rental options and prices. From there you can use our filters to narrow your search by amenities, nearby activities, ratings and more.
Are there pet-friendly vacation rentals in Oak Park?
Pack a suitcase and a bone for your beloved pooch because Oak Park has 52 vacation rentals that roll out the welcome mat to doggie guests. Let your happy hound enjoy the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates and destination, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Oak Park?
Grab your swimwear and pool noodle, because there are five houses with a private pool in Oak Park. Book a stay at one of these popular vacation homes and make every day a pool day. Simply enter your dates into Vrbo, then use the “pool” filter to find the ideal place for a splashing good time!
What are popular rental amenities in Oak Park?
The most popular rental amenities people are looking for in Oak Park include tennis, a barbecue grill and a swimming pool. Whether you’re on a trip with your besties, family or even pets, Vrbo vacation rentals provide the best amenities for hanging out with the people you love.
Are there large group vacation rentals in Oak Park?
Yes, there are 25 properties in Oak Park that can accommodate five or more guests. From family getaways to events like a friend’s birthday, these stays have ample space to hang out with the people that matter the most.
Are there vacation rentals in Oak Park that welcome kids?
Oak Park has 49 family-friendly vacation rentals to choose from. And tracking down a stay that welcomes kids is simple with our “Properties good for families” filter. Besides having the whole place to yourselves, you can also look forward to amenities and perks like dining rooms, full kitchens and private pools.
What are the top attractions for families in Oak Park?
Keeping the kids amused during your stay in Oak Park is a breeze with these leading family-friendly attractions:

  • Ernest Hemingway Museum and House
  • Unity Temple
  • Madison Street Theatre

Are there one-bedroom vacation rentals in Oak Park?
You can pick from 15 one-bedroom rentals in Oak Park. Whether you’d like a comfy cottage or a condo, our one-bedroom properties are just right if you don’t require tons of space. One of the main perks of having your own place? You won’t ever have to share your adventure with strangers.
Can I find two-bedroom vacation rentals in Oak Park?
Gather your family and enjoy peace, privacy and comfort in one of the 18 two-bedroom vacation rentals Oak Park has to offer.
Are there vacation rentals with WiFi in Oak Park?
You’ll have a choice of 29 vacation rentals with WiFi in Oak Park. If you want to disconnect from daily life during your break, but still need to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Oak Park?
Pick from 48 vacation homes with air conditioning in Oak Park providing that gentle, cool breeze and extra comfort level. Enter your dates of travel and then make use of our filter tool to locate stays with air conditioning.
How old do you have to be to rent a vacation rental in Oak Park?
You’ll need to check with the Oak Park vacation home you’re considering on Vrbo as age restrictions vary. However, typically it’s 16, 18 or 21.
How long can I rent a vacation rental in Oak Park for?
The amount of time you can book an Oak Park vacation home for is down to each property. Just tap in your travel dates to browse available options offering extended stays. They include the things you need to make your extended vacation more comfortable and enjoyable, like kitchens and air conditioning. Some vacation homes may also offer weekly or monthly discounts, so you can stay even longer for less.
Does Vrbo offer discounts for vacation homes in Oak Park?
In Oak Park, you’ll find some fantastic discounts and bargains for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re wanting a short getaway or a longer stay, we offer plenty of options to suit your needs and budget.

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