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.
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 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.
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).
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:
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.
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:
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:
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.
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:
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:
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:
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:
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.
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:
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.
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:
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.
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: