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Apartment holiday rentals in Oak Park

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Top-rated apartment rentals in Oak Park

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Top Guest favourite
The exterior of a charming brick apartment building is showcased, framed by vibrant greenery. The structure features large windows and a welcoming entryway, with a well-kept lawn and flower beds enhancing its curb appeal. The clear sky provides ample natural light.
Apartment in Forest Park
4.98 out of 5 average rating, 170 reviews

1 bedroom garden apartment in Forest Park

Unique private garden apartment in our single family residence. Great location approximately 8 miles directly west of downtown Chicago. Close to shopping, dining, entertainment and public transportation to the city. One bedroom & best for 2 people but could sleep 3 ($50 fee) for short stays. It's important to note that this is a garden/ground/lower level apartment. The ceilings are relatively low at 6.5'. This would not be the best space for tall people. Free parking in front of the house.

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, 656 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 living area features a gray sectional sofa arranged around a wooden coffee table. Soft lighting is provided by ceiling fixtures and wall-mounted sconces. The room leads to a set of stairs, while a TV is mounted on the wall for entertainment.
Apartment in Forest Park
4.85 out of 5 average rating, 167 reviews

City-Accessible Basement Retreat

Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

Guest favourite
A spacious living area is displayed, featuring a comfortable brown leather sectional sofa and a glass coffee table. A modern electric fireplace is positioned against a stone accent wall, while natural light fills the room through large windows with white blinds.
Apartment in Oak Park
4.88 out of 5 average rating, 196 reviews

Stunning 2bd 1bath w/free parking, W/D & fireplace

Whether you're here to visit family or friends, to attend a conference in the city or a quick getaway, your family will love renting our entire flat. It has all the comforts of home located on a beautiful block in the historic Frank Lloyd Wright District in Oak Park. Here, you will be close to The Frank Lloyd Wright Home/Studio, downtown Oak Park, amazing restaurants and attractions, the Green and Blue line trains that will take you to downtown Chicago, and major highways and shopping centers.

Top Guest favourite
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
4.99 out of 5 average rating, 193 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.

Superhost
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 Forest Park
4.91 out of 5 average rating, 118 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.

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.
Apartment in Oak Park
4.94 out of 5 average rating, 191 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.

Guest favourite
A two-story apartment building is shown, featuring a light-colored exterior with dual-tone siding. Lush greenery surrounds the structure, including shrubs and grass. A staircase leads to the entrance, while the nearby homes display varying architectural styles.
Apartment in Forest Park
4.85 out of 5 average rating, 372 reviews

Home in Forest Park downstairs.

Enjoy a private ground floor apartment which is centrally-located with easy access , to the city. You will have a functional kitchen, laundry facility outside your back door and fast internet. Forest Park is located about 20 minutes from downtown Chicago and about 30 minutes from O’Hara international airport. You are within walking distance of many boutiques, restaurants, parks and also public transportation. Please make a note that there will be a $30 per guest fee if more than four.

Guest favourite
The exterior of a charming brick apartment building showcases elegant architectural details, including a turret-like corner. Snow lightly covers the front steps and surrounds a mature tree, providing a peaceful winter setting. Large windows allow natural light to fill the interior spaces.
Apartment in Oak Park
4.92 out of 5 average rating, 156 reviews

Walking Distance to Everything.

This apartment is available for 1 year lease. $2400 a month fully furnished, available March 1st. The Green Line CTA "L" train is only 3 blocks away and departs every 10 minutes. Metra shares a station and departs once an hour. Freight trains also pass by. You will hear these trains train throughout the night. Most people are not disturbed by this sound. If you are a light sleeper I recommend earplugs for sleeping. Taxi from the Airport, around $80. Neighborhood parking is limited.

Guest favourite
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
4.95 out of 5 average rating, 109 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.

Guest favourite
A cozy seating area is present, featuring a leather sofa and an armchair with decorative cushions. A round glass table sits atop a woven rug, while a wicker storage box adds functionality. Natural light filters through the three large windows with blinds.
Apartment in Oak Park
4.89 out of 5 average rating, 383 reviews

Vintage Chicago-Style 1 bed, Cable & NFL PASS 40-1

→ Introducing our newly renovated and furnished apartment unit nestled in the charming Oak Park Art District. Richly characteristic brick building, Chicago style, situated in a safe and quiet neighborhood. ★ Property Features: • One block away: Oak Park Art District • Vintage Chicago style brick building • Safe, quiet neighborhood • Newly renovated and furnished • Smart TV with Cable • Free Laundry Room • Free Parking for short stays, long stays limit spots please confirm.**

Top Guest favourite
The exterior of a two-story house is shown, featuring a dark grey facade with white trim. Large windows are adorned with flower boxes displaying colorful blooms. Steps lead to a covered porch, inviting entry into the home.
Apartment in Oak Park
4.89 out of 5 average rating, 181 reviews

A Little Slice of Heaven in Oak Park, IL

A private space with a fun vintage vibe. Located several blocks from the El and the Eisenhower, it’s really easy to access the city. It also includes free off-street parking which is a must. The space is located in my basement and has a private entrance. I do live in the house above so you will hear some noises including my dog - but we do try to be quiet. The space includes a bedroom, spacious living area and an updated bathroom. Please contact me with any questions

Popular amenities for Oak Park apartment rentals

When is the best time to visit Oak Park?

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Avg. price$142 AUD$169 AUD$164 AUD$157 AUD$185 AUD$191 AUD$198 AUD$201 AUD$173 AUD$183 AUD$164 AUD$169 AUD
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Quick stats about apartment rentals in Oak Park

  • Total holiday rentals

    Explore 150 holiday rentals in Oak Park

  • Nightly prices starting at

    Oak Park holiday rentals start at $14 AUD per night before taxes and fees

  • Verified guest reviews

    Over 11,320 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    150 of Oak Park holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oak Park rentals

  • 4.7 Average rating

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

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