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Vacation rentals in Oak Park

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Quick stats about vacation rentals in Oak Park

  • Total vacation rentals

    Explore 300 vacation rentals in Oak Park

  • Nightly prices starting at

    Oak Park vacation rentals start at ﺩ.ﺇ 37 per night before taxes and fees

  • Verified guest reviews

    Over 22,070 verified reviews to help you choose

  • Family-friendly vacation rentals

    150 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wi-Fi availability

    290 of Oak Park vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Monthly stays, Gym, and BBQ grill across Oak Park rentals

  • 4.7 Average rating

    Oak Park stays receive an average rating of 4.7 out of 5 from guests

Top-rated vacation rentals in Oak Park

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost
The main room features a day bed designed for versatile sleeping, accompanied by a cozy armchair. A round coffee table sits on a natural fiber rug, while a collection of decorative plates adorns the wall. Light enters through two windows covered with blackout curtains.
Apartment in Oak Park
4.83 out of 5 average rating, 684 reviews

Sunny Jumbo Studio

Bright and sunny Oak Park jumbo garden studio, steps from cute downtown, train to Chicago, and amazing local tourist destinations- like the Hemingway Home and the Wright Studio. This welcoming studio was completely rehabbed and updated. We put a lot of care into designing a relaxing apartment with all the amenities. The main room features a king-sized bed, office nook, and fully stocked entertainment area, with games, books, and a TV. The spacious kitchen and luxurious bathroom are brand new!

ValueLocationTV

Top guest favorite
A comfortable living area features a light gray sofa adorned with colorful pillows. A small wooden coffee table with intricate designs sits in front of the sofa, accompanied by a floral arrangement. Art pieces hang on the walls, and natural light enters through the large window.
Apartment in Oak Park
4.92 out of 5 average rating, 148 reviews

Cheerful Remodel Prime Location

Relax in this newly remodeled and beautifully decorated apartment while recharging from a long day of sightseeing in the big city! We are a block from the Green Line train to downtown! With a 5 minute walk to Whole Foods, Trader Joes, and downtown Oak Park, you can't get a better location than this! Pets are welcome on a case-by-case basis, please mention your pet in your inquiry so we can learn more about them prior to approval and be sure to register them when you select number of guests.

ValueLocationHeating

Top guest favorite
A bright living area with a sloped ceiling features a comfortable blue sofa and light-colored armchairs. A small marble-top table is set with two cups. A desk is positioned near a window, and a decorative rug adds warmth to the hardwood floor.
Guesthouse in Oak Park
4.97 out of 5 average rating, 130 reviews

Oak Park cozy carriage house-lovely, walkable area

Our comfortable, stylish retreat has everything you need to relax and recharge. Whether you are visiting to explore all that beautiful Oak Park and downtown Chicago offer or desire a peaceful space to work. -> Quiet, walkable street near popular cafes, restaurants, taverns, parks, historic homes -> Steps from the "L" Blue Line Oak Park station -> Stocked w/ snacks + gourmet coffee/tea set-up (grinder, AeroPress, and Keurig) -> Onsite off-street parking -> A/C + heat -> garden sitting area

ValueLocationComfort

Top guest favorite
Townhouse in Oak Park
4.99 out of 5 average rating, 76 reviews

A Pleasant Stay in Oak Park

Welcome to our bright and peaceful townhouse in Oak Park, IL! Just steps from the vibrant Oak Park Arts District, you'll be close to the area’s best shops and restaurants. Recently renovated from top to bottom, the home features high-quality materials and a clean, modern style that beautifully honors its vintage charm. Located in a residential neighborhood step to the train, downtown Oak Park and 15 minutes to Chicago. We offer a calm and stylish space where guests can relax and unwind.

FamilyValuePool

Top guest favorite
Apartment in Oak Park
5.0 out of 5 average rating, 91 reviews

Stylish & Spacious Duplex Near Downtown w/Parking

2024 Gut rehab! Spacious w/A+ location! 1 of 2 apts in a two flat. King bed! W/D! This unit = Main floor + finished bsmnt. 3 bdrms + 2.5 baths. Steps to FLW Home. 20 min to downtown Chicago. Walk to dining + train. Open living/dining/kitchen/sunroom. Powder room. Primary w/king + ensuite. 2nd bedroom w/queen + 3rd bedroom w/2 double beds, walk-in closet. 2nd full bath + work/gameroom. Coffee bar, pantry. Private entry/deck. Driveway parking. Upstairs apt not included in this listing.

FamilyLocationCheckout

Superhost
Apartment in Oak Park
4.86 out of 5 average rating, 22 reviews

Guest Favorite Stay in Oak Park| In Unit Laundry

2nd-floor unit with elevator access. Older building with radiant heat managed by the building. Includes an all-in-one electric washer and dryer. Welcome to your stylish Oak Park retreat! This newly remodeled 2BR/2BA apartment blends modern comfort with historic charm. Enjoy a bright space with a full kitchen, cozy living area, and designer touches. Walk to shops, cafes, and parks, or use nearby transit for easy access to Chicago. Perfect for families, friends, or business stays.

FamilyLocationHospitality

Top guest favorite
A lush garden surrounds a charming historic home, with greenery and flowers creating a vibrant landscape. A shaded seating area is provided under an umbrella, offering a space for relaxation amidst the natural beauty. The home is partially covered in climbing vines, enhancing its character.
Apartment in Oak Park
4.95 out of 5 average rating, 125 reviews

Studio Apartment in Oak Park

Nestled in Oak Park's historic district, this charming studio apartment is within walking distance of cafes, shops, restaurants, a movie theater, and the CTA/Metra for city and suburban excursions. Featuring a comfortable queen-sized bed, a newly updated full bathroom, and a kitchenette, it sits mere steps from Ernest Hemingway's childhood home and a few blocks from Frank Lloyd Wright's residence and studio. Enjoy the serenity of this historic home and its hidden garden oasis.

FamilyLocationBackyard

Guest favorite
A stylish studio features a spacious bed adorned with colorful pillows. A cozy seating area with a dark sofa is positioned near large windows that allow natural light to fill the room. A small dining table with chairs sits beside the sofa, enhancing the open layout.
Apartment in Oak Park
4.92 out of 5 average rating, 59 reviews

Modern NEW Deluxe Studio in Oak Park

Enjoy a stylish experience at this centrally-located studio In charming Oak Park. Tourist-friendly and trendy downtown Oak Park has a buzzing restaurant district, great cafes, and an assortment of excellent storefronts, including vintage shops, boutique toy stores, mom-and-pop bookstores, and a variety of spas and salons to choose from. Parks in this world-class suburb are everywhere. Views from the unit are fabulous. This deluxe studio has it all.

ValueLocationKitchen

Guest favorite
A charming Victorian home is showcased, featuring a front porch with wide steps leading to a door framed by lush greenery. The exterior is painted in a crisp white, complemented by dark accents on the windows. A manicured lawn adds to the inviting landscape.
Home in Oak Park
4.96 out of 5 average rating, 141 reviews

Oak Park Victorian by FLW Studio

Discover historic charm in our updated 4-bedroom Victorian home in the iconic Frank Lloyd Wright district. Comfortably sleeps 8. Features a fully equipped kitchen, dedicated workspace, and modern amenities. Perfectly located for exploring local gems on foot or a quick 15-min drive to downtown Chicago. Enjoy private parking and easy access to public transit. Ideal for families and groups seeking a stylish, central retreat.

LocationValueCheck-in

Guest favorite
The living area features a futon couch in a light tone, paired with a blue accent chair. A round coffee table sits on a patterned area rug, beneath ample natural light from large windows covered with light curtains. A small dining area is positioned nearby.
Guesthouse in Oak Park
4.89 out of 5 average rating, 131 reviews

Sunny Coach House in Historic Oak Park

This bright, cozy coach house is your ideal base in Oak Park. It was originally the coachman's quarters behind a 1909 Prairie-style house, now converted into guest lodging with all the modern amenities above a detached garage. The coach house is at the end of a long driveway (free parking included!) on a quiet street, in the heart of the Frank Lloyd Wright district, a short walk from trains to downtown Chicago.

FamilyValueGetting around

Guest favorite
The living space features a comfortable sofa and an armchair, arranged around a coffee table. A television is mounted on the wall, and natural light pours in through two windows. Decorative artwork adorns the walls, enhancing the welcoming ambiance.
Condo in Oak Park
4.8 out of 5 average rating, 387 reviews

Peaceful Oak Park Condo Next to Green Line Metro

Very private, quiet space amidst the activity of Downtown Oak Park. The layout of the space is ideal, as bedrooms are at one end, and the living space is at the other. Private outdoor deck. Oak Park is a beautiful neighborhood full of great places to eat, drink, and shop. Metro and Green line is steps away which means access to anywhere in the city of Chicago. Private parking too!

ValueLocationQuiet

Top guest favorite
A bright living area features a brown sofa adorned with a green accent pillow, positioned in front of a simple black coffee table. Natural light enters through multiple windows, illuminating the space. Decorative wall art and a unique mirror enhance the inviting atmosphere.
Apartment in Oak Park
4.98 out of 5 average rating, 380 reviews

Bright & Spacious Victorian-FREE PKG walk to train

This historic Queen Anne home built in 1889 is in the heart of Oak Park. Walk to all tourist attractions, public transportation that takes you directly to downtown Chicago, great restaurants, boutiques and grocery stores. It’s the perfect base for exploring Oak Park and Chicago. We kindly ask that you read our full listing description and our house rules prior to booking.

ValueFamilyAmenities

Popular amenities for Oak Park vacation rentals

Monthly staysGymBBQ grillLaptop-friendly workspaceWifi

Stay near Oak Park's top sights

Frank Lloyd Wright Home and Studio

241 locals recommend

Ernest Hemingway Birthplace

107 locals recommend

Fitzgerald's

93 locals recommend

Oak Park Conservatory

58 locals recommend

Unity Temple

37 locals recommend

Pleasant Home

30 locals recommend

Other great vacation rentals in Oak Park

Top guest favorite
Decorative elements are displayed on a mantel, featuring two sculptural figures crafted from textured metal. A collection of books about Oak Park is arranged alongside dried floral arrangements, adding to the aesthetic appeal of the space.
Apartment in Oak Park
4.98 out of 5 average rating, 88 reviews

Historic Hotspot: Downtown Oak Park w/parking spot

ValueLocationBackyard

Superhost
Apartment in Oak Park
5.0 out of 5 average rating, 5 reviews

3BR/1BA With Private Garage, Near Train & Shops

LocationParkingSleep quality

Guest favorite
A spacious living area features a modern sectional sofa adorned with decorative pillows. Two bedside tables and lamps provide soft lighting, while a wooden coffee table sits on a vibrant area rug. A framed cityscape photograph decorates the wall, enhancing the room's character.
Apartment in Oak Park
4.94 out of 5 average rating, 64 reviews

Restored Mid-Century 4 Square

LocationValueWalkability

Superhost
Home in Oak Park
4.82 out of 5 average rating, 28 reviews

OakPark Gem. Family-Friendly Getaway near Downtown

LocationFamilyCondition

Guest favorite
A spacious living room features a light-colored sofa and a glass coffee table, accompanied by a decorative pouf. Large windows provide ample natural light, highlighting a grand piano in the corner. A dining area is visible through the archway, showcasing a wooden table and chairs.
Apartment in Oak Park
4.93 out of 5 average rating, 94 reviews

First floor of Historic Oak Park Villa, Grge:2Cars

FamilyValueNearby

Top guest favorite
Condo in Oak Park
5.0 out of 5 average rating, 18 reviews

Architect-Designed 2BR Oak Park Flat

FamilyLocationOutdoor spaces

Top guest favorite
A comfortable living area features a beige sofa adorned with decorative pillows, complemented by a large window allowing natural light. A ceiling fan enhances the airflow, while a flat-screen TV is positioned on a wooden media console. Indoor plants add a touch of greenery.
Apartment in Oak Park
4.91 out of 5 average rating, 45 reviews

Explore Oak Park & Chicago

FamilyLocationQuiet

Top guest favorite
Apartment in Oak Park
5.0 out of 5 average rating, 31 reviews

2nd Floor Apartment in the Heart of Oak Park

LocationFamilyWalkability

When is the best time to visit Oak Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 353ﺩ.ﺇ 375ﺩ.ﺇ 419ﺩ.ﺇ 430ﺩ.ﺇ 529ﺩ.ﺇ 555ﺩ.ﺇ 518ﺩ.ﺇ 514ﺩ.ﺇ 441ﺩ.ﺇ 437ﺩ.ﺇ 404ﺩ.ﺇ 378
Avg. temp-3°C-1°C4°C10°C16°C22°C25°C24°C20°C13°C6°C0°C

Frequently Asked Questions

  • What are the best places to stay in Oak Park?

    Stays near downtown Oak Park are often recommended for easy access to dining, shopping, and transit. Neighborhoods close to parks or historic districts have a quieter ambiance and blend community with convenience.

  • What are the best things to do in Oak Park with kids?

    Families often explore interactive exhibits at the Children’s Museum, play in Scoville Park, or visit local libraries for storytime. Many parks have playgrounds, and seasonal events provide hands-on activities for children.

  • What are some of the best things to do in Oak Park?

    Discover Oak Park’s historic architecture, visit local museums, and attend community theater or art shows. Independent shops, farmers markets, and neighborhood parks add variety to daily adventures.

  • How is the weather in Oak Park?

    Oak Park has cold winters around 19–33°F (-7–0°C), while summers bring warmer afternoons near 68–85°F (20–29°C). Spring and autumn have milder temperatures and occasional rain, so packing layers is helpful.

  • When is the best time to visit Oak Park?

    Late spring through early fall is often recommended, with warmer temperatures and outdoor festivals. Winter has lower temperatures, so pack accordingly if you plan to visit during colder months.

  • What are the best places to visit in Oak Park?

    Explore the Frank Lloyd Wright Home and Studio, the Ernest Hemingway Birthplace Museum, and Scoville Park for a glimpse of local history. Art galleries and cultural centers around downtown highlight Oak Park’s creative roots.

  • What are some hiking trails in Oak Park?

    Oak Park has tree-lined walking paths in local parks, such as Austin Gardens and Lindberg Park. Trail enthusiasts often explore nature preserves around the area or venture into nearby forested spaces for varied experiences.

  • What are some family activities we can do in Oak Park?

    Families can explore parks with playgrounds, join events at the local library, or visit interactive museum spaces. Community centers and seasonal festivals provide hands-on fun for all ages.

  • What are some of the best day trip ideas from Oak Park?

    Nearby areas have cultural museums, nature preserves, and lakeshore parks that are often recommended for day trips. Chicago's downtown, with its theaters and riverfront walks, is a frequently suggested destination for visitors.

  • Are there any pet friendly accommodations available in Oak Park?

    Several Oak Park vacation rentals welcome pets, especially houses and ground-floor apartments near green spaces. Local parks such as Lindberg Park make outings with your dog convenient.

  • What are some local tips for visiting Oak Park?

    Consider exploring Oak Park by foot or bicycle to appreciate historic architecture and murals. Locals suggest sampling small businesses, packing layers for unpredictable weather, and checking out neighborhood events to connect with the community.

  • What is Oak Park known for?

    Oak Park is known for its historic architecture, including several Frank Lloyd Wright-designed homes, its literary heritage linked to Ernest Hemingway, and vibrant community arts. The area has diverse eateries and independent shops.

  • What are the best hidden gems to explore in Oak Park?

    Oak Park has lesser-known murals and community gardens that locals often highlight. Small galleries, independent bookshops, and historic alleys near the arts district offer quiet places to explore.

  • What are the best foods to try in Oak Park?

    Oak Park has a mix of locally rooted cuisines, with pizza, classic Chicago-style hot dogs, and diverse vegetarian dishes frequently suggested. Independent bakeries, global eateries, and seasonal farmers market fare round out the food scene.

  • What should I bring for a trip to Oak Park?

    Pack versatile layers, as temperatures range from around 19°F (-7°C) in winter to 85°F (29°C) in summer. Comfortable shoes are helpful for walking through historic districts and parks, and a reusable water bottle suits busy days out.

  • What is the nightlife in Oak Park like?

    Oak Park has neighborhood bars, music venues, café lounges, and spots with occasional live performances. The scene is relaxed, with locals gathering for casual dining, craft drinks, and community events.

  • What are the most popular events or festivals in Oak Park?

    Oak Park hosts seasonal festivals, including an arts-focused event often recommended in summer and community celebrations around Labor Day weekend. Local farmers markets and neighborhood block parties are also frequently suggested.

  • Are there family friendly vacation rentals in Oak Park?

    Oak Park has a variety of family-friendly vacation rentals, including apartments and houses near parks and schools. Many hosts include amenities such as play spaces, high chairs, and board games.

Destinations to explore