Airbnb your place

Holiday rentals in Oak Park

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Oak Park

  • Total holiday rentals

    Explore 300 holiday rentals in Oak Park

  • Nightly prices starting at

    Oak Park holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 22,070 verified reviews to help you choose

  • Family-friendly holiday rentals

    150 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wifi availability

    290 of Oak Park holiday rentals include wifi 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 holiday rentals in Oak Park

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

1 of 1 pages1 / 1
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.
Flat 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!

Superhost
A spacious bedroom is furnished with a large bed featuring a gray and white patterned blanket. Art pieces are displayed on the wall above the bed, and two bedside lamps with warm light sit on either side. A bold, geometric area rug adds texture to the space.
Guest house in Oak Park
4.91 out of 5 average rating, 268 reviews

Gallery Loft of Oak Park #1 Top Host in IL

Gallery Loft of Oak Park <a href="https://news.airbnb.com/the-number-one-new-host-in-each-us-state/">2021 #1 Top Host in Illinois</a> is a Chicagoland gem near the birthplace of Ernest Hemingway, Frank Lloyd Wright Home/Studio. 2nd story flat furnished in vintage mcm style, featuring local artists. Walking distance to live music (Fitzgerald's, Friendly Music Community), and restaurants. Firepit access, easy street parking and kitchen well stocked. Private porch. Perfect long/short term stays.

Top guest favourite
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.
Guest house 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

Top guest favourite
Flat in Oak Park
4.98 out of 5 average rating, 93 reviews

Open & Sunny Treetop Oasis Near Downtown w/Parking

Take a deep breath and relax in this airy and bright top floor apartment. Treetops surround the newly renovated and spacious home in a premier Oak Park location. 20 min. to downtown Chicago. Only 1/2 block to the FLW Home & Studio. Walk to dining & train. 2 bedrooms & 1 bath w/tub & shower. Open living/dining/kitchen/sunroom. Wow kitchen w/huge island. Primary w/king bed + deep closet. 2nd bdrm w/built-in bunk beds + desk + balcony. Private entry & deck. Shared fenced yard. Driveway parking.

Top guest favourite
Double French doors open into a bright, inviting living space. A patterned area rug lays on polished hardwood floors, leading to a cozy seating area with upholstered chairs. Decorative artwork adorns the walls, and soft light filters in through the windows.
Flat in Oak Park
4.95 out of 5 average rating, 205 reviews

A Quiet Stay While You Are Away Oak Park

Welcome to our cozy and comfortable home located in a quiet neighborhood. Our space is perfect for couples, solo travelers, small families, and long-term stays. This is a beautiful, modernist home located in the Frank Lloyd Wright District Neighborhood, a designated historic district known for its collection of homes designed by the famous architect Frank Lloyd Wright. This district features a collection of some of his iconic designs and is a destination for architecture enthusiasts.

Superhost
Flat in Oak Park
5.0 out of 5 average rating, 4 reviews

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

Welcome to our beautiful, modern, and spacious apartment in Oak Park's Gunderson Historic District! Walk to the park, train station, shops, and restaurants in this highly walkable neighborhood. The apartment features 3 bedrooms with 3 queen beds, 1 large bathroom, a sofa, and an inflatable mattress upon request. Enjoy fast Wi-Fi, a fully stocked kitchen, an in-unit washer/dryer, and a private garage parking space. Perfect for work or vacation, just 15–20 minutes from downtown Chicago!

Superhost
Flat 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.

Top guest favourite
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.
Flat 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.

Guest favourite
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.
Flat in Oak Park
4.94 out of 5 average rating, 64 reviews

Restored Mid-Century 4 Square

A group up to four will enjoy easy access to everything from our centrally located getaway. This extra large 4 room 1 bedroom + 3 season porch with swing is the ideal retreat after a day of working or sightseeing around Chicago. This one bedroom, king suite with sofa sleeper, encompasses the first floor of the building. There are 7 stairs to get into the unit. Off street parking on the driveway is included.

Top guest favourite
A historic Queen Anne home features a distinctive turret and a wraparound porch, surrounded by lush greenery. The exterior showcases a blend of siding and masonry with intricate architectural details reflective of its 1889 origins.
Flat in Oak Park
4.98 out of 5 average rating, 269 reviews

Chic Retreat in Historic Victorian House-Park Free

This historic Queen Anne home built in 1889 is in the heart of Oak Park. Centrally located and within walking distance to all tourist attractions, public transportation, great restaurants, boutiques and grocery stores. It’s the perfect base for exploring Oak Park and Chicago Perfect for long-term stays. We kindly ask that you read our full listing description and our house rules prior to booking.

Luxe
Apartment in Oak Park
5.0 out of 5 average rating, 14 reviews

Architect-Designed 3BR Oak Park Flat

Experience historic Oak Park in our beautifully renovated 3-bedroom apartment. Blending 1920s charm with modern luxury, this space comfortably fits families or groups. Features a dedicated workspace, new kitchen, and a shared roof deck. Located steps from the Green Line, offering a quick, direct ride to downtown Chicago. Perfect for exploring both Oak Park's cultural gems and the Windy City.

Guest favourite
The kitchen features a spacious layout with a farmhouse sink and modern appliances, including a dishwasher and gas stove. Colorful backsplash tiles add a playful touch. Natural light enters through two windows, illuminating the black marble-like flooring and nearby shelves filled with utensils.
Home in Oak Park
4.89 out of 5 average rating, 61 reviews

Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

This Arts District located beautiful Retro Cottage 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.

Popular amenities for Oak Park holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

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 holiday rentals in Oak Park

Guest favourite
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.
Flat in Oak Park
4.93 out of 5 average rating, 94 reviews

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

Top guest favourite
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.
Flat in Oak Park
4.98 out of 5 average rating, 88 reviews

Historic Hotspot: Downtown Oak Park w/parking spot

Guest favourite
A sofa is adorned with an array of textured cushions in neutral tones. A framed artwork depicting a historic street scene is displayed above the sofa. A bouquet of fresh flowers in a decorative vase adds a touch of natural beauty to the setting.
Flat in Oak Park
4.91 out of 5 average rating, 81 reviews

Scrumptious 2nd floor Abode

Top guest favourite
Flat in Oak Park
5.0 out of 5 average rating, 68 reviews

Serene 1-Bedroom Suite in Oak Park (Free Parking!)

Guest favourite
A blue Victorian-style house is framed by a lush green lawn and several trees. The structure features a prominent gabled roof and a welcoming porch with steps leading to the entrance. Surrounding foliage adds to the home's charm.
Flat in Oak Park
4.94 out of 5 average rating, 33 reviews

Large 2 BR Apt in FLW Historic Dist. in Oak Park!

A cozy studio is presented with multiple spaces, featuring a spacious bed, a modern kitchen area, and a comfortable workspace. Natural light filters through the windows. Decorative elements include wooden furniture and subtle wall art, creating an inviting living environment.
Flat in Oak Park
4.91 out of 5 average rating, 108 reviews

Studio Mins Walk to DT OAK PARK

A cozy living area features a black leather sectional sofa adorned with colorful pillows. On the walls, blue accents frame acoustic guitars, while a framed photo adds interest. A round light illuminates the space, complemented by a side table holding books and a decorative item.
Flat in Oak Park
4.81 out of 5 average rating, 237 reviews

Friendly Rock ’n’ Roll Retreat

An inviting living area features a light-colored sofa and two brown leather chairs arranged around a wooden coffee table on a patterned area rug. A dining table is visible in the background, alongside a modern kitchen, while large windows allow natural light to fill the room.
Flat in Oak Park
4.84 out of 5 average rating, 216 reviews

Small But Mighty 700 Sqft Cottage Apt (1BR/1BA)

When is the best time to visit Oak Park?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$123 SGD$131 SGD$146 SGD$150 SGD$185 SGD$194 SGD$181 SGD$179 SGD$154 SGD$153 SGD$141 SGD$132 SGD
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