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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 G$2,093 GYD 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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Top guest favorite
Apartment in Oak Park
5 out of 5 average rating, 93 reviews

Curated & Spacious Duplex Near Downtown w/Parking

A warm, curated home with two floors of living space. Perfect for families with kids, groups of friends and multi-generational living. The main floor + finished basement total 3 bdrms + 2.5 baths. Primary suite is on the main floor. Two secondary bedrooms are on the lower w/ a full bath. 20 min to downtown Chicago. Walk to dining + train+ FLW Home. Open living/dining/kitchen/sunroom. Remote work space. Coffee bar. Private entry/deck. Driveway parking. Central AC. Upstairs apartment is separate.

FamilyValueBiking

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, 685 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!

ValueLocationOutdoor spaces

Top guest favorite
A bright living room features a cozy seating arrangement with a variety of armchairs and a sofa. Original art pieces adorn the walls, and a coffee table with a decorative table runner sits on a soft area rug. Light streams in through windows creating a lively atmosphere.
Apartment in Forest Park
5 out of 5 average rating, 222 reviews

Sunny 1 bedroom apartment 1 block from restaurants

This sunny second floor apartment perched in an 1890’s farmhouse offers traditional charm with many contemporary touches. It showcases a variety of original art. Located on a quiet street but just steps away from restaurants, bars and shops, off-street parking is included. Two nearby trains provide easy access to downtown Chicago and O’Hare Airport. An enclosed porch directly off the kitchen overlooks a beautiful prairie garden. You can relax on the backyard patio with gas grill and fire pit.

ValueFamilyQuiet

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, 150 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.

LocationValueWifi

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.
Guesthouse 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.

FamilyValueParking

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, 133 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

ValueLocationBackyard

Guest favorite
A bright living room features multiple windows allowing natural light to fill the space. A yellow armchair and a dark sofa are arranged around a central wooden table. A decorative rug adds warmth to the hardwood floor, complemented by a lamp and an entertainment unit.
Apartment in Oak Park
4.96 out of 5 average rating, 127 reviews

Top floor of Historic Oak Park Home /2 Car Garage

Secluded but never isolated; 3 blocks from the L-line, next door to Hemingway's birthplace, surrounded by dozens of Frank Lloyd Wright homes, 30 min from the Loop, MDW and ORD, makes this location an ideal platform for the cultural explorer. Experience an ambiance that supports the work-from-home Urban Professional, combining it with a multibedroom layout designed to accommodate family and friends. Gig-speed internet supports sophisticated professional and gaming applications.

FamilyLocationWalkability

Guest favorite
A cozy living room features four plush purple chairs arranged around a circular table. A modern television is mounted above a white brick fireplace, complemented by bookshelves filled with various items. A large potted plant adds a touch of greenery, enhancing the warm atmosphere.
Home in Oak Park
4.88 out of 5 average rating, 103 reviews

A Comfortable Stay While You are Away in Oak Park

Welcome to this Oak Park home, conveniently minutes from the main expressway, train station, downtown Chicago, and the Medical Center. This entire Oak Park house is ideal for travelers seeking a tranquil and welcoming space to unwind in after a long day, medical professionals, visiting patients at the Medical Center, and families needing long-term housing. The residence is minutes from downtown Oak Park and the historical landmarks of Frank Lloyd Wright's home and studio.

ValueLocationBathroom

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, 142 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.

ValueLocationQuiet

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, 133 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.

LocationValueCheckout

Top guest favorite
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.
Apartment 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.

FamilyValueParks

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!

ValueFamilyParking

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
Apartment in Oak Park
5 out of 5 average rating, 6 reviews

Comfortable & Easy

LocationValueCondition

Guest favorite
A charming two-story house with a white exterior is surrounded by neatly trimmed greenery. Large windows provide ample natural light. The front porch features a staircase leading to the entrance, while tall hedges and a manicured lawn frame the property.
Apartment in Oak Park
4.87 out of 5 average rating, 332 reviews

Cosmopolitan Nest in Oak Park North Side

LocationFamilyCheck-in

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

LocationValueWifi

Guest favorite
A spacious living area is depicted, featuring a comfortable corner sofa adorned with soft pillows. A large flat-screen TV is mounted on the wall, positioned across from a stylish dining table with six black chairs. A patterned area rug adds warmth to the hardwood floor.
Apartment in Oak Park
4.82 out of 5 average rating, 56 reviews

Cozy & Stylish 1 BD Near City+Airport

FamilyValueIndoor spaces

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

2nd Floor Apartment in the Heart of Oak Park

FamilyValueIndoor spaces

Guest favorite
Apartment in Oak Park
4.87 out of 5 average rating, 23 reviews

Guest Favorite Stay in Oak Park| In Unit Laundry

FamilyLocationWalkability

Superhost
Apartment in Oak Park
5 out of 5 average rating, 3 reviews

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

ValueHospitalityDecor

Top guest favorite
A remodeled kitchen features a large island with three wooden stools and a copper accent. A vintage red refrigerator stands against a backdrop of grey cabinets and an exposed wooden beam ceiling. Open shelves showcase kitchenware alongside rustic decor elements.
Home in Oak Park
4.99 out of 5 average rating, 77 reviews

Oak Park - Wine House!

ValueLocationDecor

When is the best time to visit Oak Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$20,093 GYDG$21,348 GYDG$23,860 GYDG$24,488 GYDG$30,139 GYDG$31,604 GYDG$29,511 GYDG$29,302 GYDG$25,116 GYDG$24,906 GYDG$23,023 GYDG$21,558 GYD
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