Discover a selection of 2,000 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 parking. Prices start at $96 per night, and houses and condos 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.

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 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).

What are the top vacation rentals in or near Oak Park?

Whether you're after a cozy escape for you and your sweetheart or somewhere spacious to fit all your friends, you'll find some top vacation rentals in and around Oak Park. Here are a couple we think you'll like:

  • Around 11 miles from the center of Oak Park, it's hard to beat "Luxury Loyola 3 Bedroom, 2 Bath". It has 3 bedrooms and handy features including a toaster and WiFi.
  • Alternatively, unpack your bags at "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental". Located around 8 miles from the heart of Oak Park, it has 3 bedrooms and features golf and a stovetop.

For even more great options, use the search bar at the top of the page to find the perfect Oak Park vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Oak Park?

Clock off on Friday and then forget the real world. If it's time for some relaxation and fun, these escapes in and near Oak Park promise the perfect weekend getaway:

  • Escape the daily grind at "53th Floor Magmile Penthouse - Views", which is around 8 miles to the east of Oak Park. There's lots of adventure and nature to keep you on the go here. Try hiking and biking and windsurfing or simply take in the sights of Osaka Garden and Creekside Park.
  • Alternatively, take some time out at "52nd Floor Magmile Penthouse - Views". About 8 miles east of Oak Park, fun activities around here include sailing and golf. Prefer to go sightseeing? Pencil in a visit to St Andrews Golf and Country Club and Royal Golf Club at Klein Creek.

Can I find studio apartments for rent in and around Oak Park?

Usually small in size, economical and well located, it's easy to fall for the appeal of a studio apartment. Make yourself comfortable in one of these vacation rentals and discover the culture of Oak Park up close:

  • Put your bags down and your feet up at "52nd Floor Magmile Penthouse - Views". Amenities including a TV and a fireplace help make guests feel right at home here.
  • Another top choice is "51st Floor Magmile Penthouse - Views". Make use of an ice maker, towels and other convenient amenities during your stay.

When it's time to step out of your studio apartment and explore, there's loads to keep you amused around Oak Park. Enjoy cultural attractions? Visit Lookingglass Theatre and Provision Theater.

Can I find short term rentals in or near Oak Park?

Short-term rentals are plentiful in and around Oak Park. Stay for a night or two in a luxury cabin, a compact apartment or a spacious house. No matter what type of vacation rental you're searching for, you'll find what you need with Vrbo. Here are some of our top picks:

  • Nice and close to the center of Oak Park, "51st Floor Magmile Penthouse - Views" is ideal for a short and sweet break. While you're in the area, check out top attractions like Wrigley Field and McCormick Place.
  • Eat, sleep and discover your surroundings from "52th Floor Penthouse - Fireplace", another exceptional option. Millennium Park and Willis Tower should be on your to-do list when you're ready to go sightseeing.

What are the best romantic weekend getaways in or near Oak Park?

Whether spent in a cabin, a cottage or a condo, a romantic weekend getaway is a fantastic way to add some zing to your relationship. Whisk your partner away for a couple of days at one of these escapes in or near Oak Park:

  • Sneak off on Friday afternoon for a couple of passion-filled evenings at "Luxury Loyola 3 Bedroom, 2 Bath". Around 11 miles from Oak Park, it comes with lots of nice touches, including beauty services and shopping facilities.
  • "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental" is another retreat that's guaranteed to impress. It's approximately 8 miles from Oak Park and has housekeeping services and air conditioning.

Are there mansions for rent in or near Oak Park?

If you're looking for somewhere to reconnect with loved ones this vacation, why not make it extra special? These mansions for rent in or around Oak Park will easily accommodate the entire gang while doing it in style:

  • Around 25 miles to the southwest of Oak Park is "Mansion With Pool, Theater, Game Room In A Golf Community". As well as its grand design and posh interiors, you'll be impressed by its top-notch amenities, such as golf and a swimming pool.
  • Another popular option is "Beautiful 9bedroom Mansion With 4 Parking Spots. Walk To Wrigley Field And Lake Michigan". Approximately 9 miles to the northeast of Oak Park, this opulent vacation rental represents the height of high-class living and offers a firepit, beauty services and more.

What are the best houses for rent with a pool in or near Oak Park?

Nothing spells fun like a pool. Blow up your unicorn floatie and check out these houses in or near Oak Park that come with this vacation perk:

  • Round up your crew and enjoy a memorable break at "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental". There's plenty to love about this retreat apart from its pool, such as a barbecue grill and childrens activities.
  • Spend lazy days swimming or catching a few peaceful moments beside the water at "New Oak Park House - 11 Mi From Downtown Chicago". This vacation home is another sought-after option and features towels, a microwave oven and more.

Not sure how to pack your suitcase for your Oak Park break? This enticing destination has a humid continental climate. In the summertime, expect average temperatures of between 65 ºF and 75 ºF. Look up our range of Oak Park vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more great ideas about where to stay.

What are the best large family vacation rentals in or near Oak Park?

You'll always have more fun sharing those precious memories with the folks you care about the most. Whether you're organizing a family catch-up or taking time out with good friends, we'll have a large vacation rental to suit your needs. Here are two of our best in and around Oak Park:

  • Located about 8 miles to the northeast of Oak Park, "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental" has 3 bedrooms and sleeps up to 8 guests. It comes with lots of amenities, including free toiletries and a fridge.
  • "Views, Pool, Fireplace, Fitness Center" also offers the space you need to connect with loved ones. This rental is around 8 miles to the east of Oak Park, and accommodates 8 guests in its 3 bedrooms. Coffee and tea making facilities and a balcony will help keep everyone comfortable and content.

When it's time to step outside your front door, there are lots of family-friendly attractions nearby to keep everyone happy. Skydeck Ledge, Navy Pier and John G. Shedd Aquarium should be on your agenda.

What are the best large houses to rent with indoor pools in or near Oak Park?

Go for a dip anytime you please when you choose one of our large rental houses with an indoor pool. Slip on your swimsuit and consider these escapes in or near Oak Park that boast this premium perk:

  • Invite your closest friends over for a refreshing swim at "Cozy 4 Bedroom/2 Bath Cozy Home In East Glenview With Inground Pool". This home has space to spare, with 4 bedrooms sleeping up to 7 guests. A fireplace and a kitchen are other things your team will love about this place.
  • Alternatively, spend your break at "3b/2. 5ba Luxury Penthouse With Views", which has 3 bedrooms and caters for up to 8 guests. Along with that fancy pool at your fingertips, a sauna and a kitchen will help keep everybody comfortable and content.

Want to see more options? Find your ideal stay by using the search bar at the top of the page. Simply adjust the filters to find the Oak Park vacation rental that's perfect for you.

Are there one-bedroom vacation rentals in or near Oak Park?

Idyllic romantic retreats, business trips or solo adventures — a single-bedroom rental property is an ideal solution for a multitude of occasions. One of these options in or near Oak Park is sure to impress:

  • Take a sneak peek at "Calm And Serene - Downtown Oak Park", a fabulous centrally located one-bedroom vacation property. A kitchen and an oven are among its useful amenities.
  • "Boho Retreat - Downtown Oak Park" is another stylish one-bedroom escape also a hop, skip and a jump from the center. When you're not out exploring the surrounds, take advantage of a kitchen, an oven and more.