Apartment vacation rentals in Oak Park

A cozy seating area is highlighted by a modern electric fireplace beneath a mounted television displaying streaming options. Soft cushions and a pastel throw blanket add comfort to the light-colored chair. A touch of decor is presented with wall art and a small side table.

4.91 out of 5 average rating, 200 reviews

Lovely, spacious 2bd, 1bath home w/free parking

Bring the whole family to enjoy this great place with lots of comforts and space. Beautifully decorated with reclaimed barn wood throughout the home and a completely remodeled kitchen with cute bistro table to enjoy your coffee. Wonder around this beautiful, quiet Frank Lloyd Wright neighborhood to see beautiful Victorian homes and architect or take a brisk walk to downtown Oak Park before taking in the sites in Downtown Chicago. Whether you stay for a while or a few days, welcome home!

A spacious living area is highlighted by a black sofa facing a light-colored coffee table. A vibrant area rug adds color underfoot. The walls are adorned with colorful vinyl records and framed artwork, while original woodwork details frame the open layout leading to the dining area.

4.87 out of 5 average rating, 707 reviews

Rockin' 2Bed steps to shops/food/train

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

Apartment in Jefferson Park

A living area features a dark leather sofa with red accent pillows, paired with two leather chairs. A wooden coffee table sits centrally, surrounded by warm-toned lighting. The space opens to a kitchenette with a retro red refrigerator and tall bar seating, creating an inviting atmosphere.

4.86 out of 5 average rating, 249 reviews

Cozy & Comfy 1bd In Historic Portage Park Bungalow

Make yourself at home in my comfortable Portage Park one bedroom garden apartment. This spacious condo is bright and airy with warm furnishings, a kitchenette with an island, private bedroom with a full bed and a modern bathroom with a glass walk-in shower. Portage Park is Chicago’s largest Polish neighborhood and is home to vintage charm, heaps of history and classic Chicago-style bungalows. The National Veterans Art Museum is a poignant must-see while you’re here with its combat-era art.

The living area features a comfortable white leather sofa and a reclined chair beside a light wood table. Natural light streams through triple windows adorned with blinds. A decorative fireplace and a wall-mounted TV enhance the space's functionality.

4.88 out of 5 average rating, 428 reviews

Chicago-Style, Vintage, Cable & NFL PASS 42-1

→ Introducing our newly renovated and furnished apartment unit nestled in the charming Oak Park Art District. Experience vintage Chicago style living in this richly characteristic brick building, situated in a safe and quiet neighborhood. ★ Property Features: • One block away from the Oak Park Art District • Vintage Chicago style brick building • Safe, quiet neighborhood • Newly renovated and furnished • Smart TV with Cable and option to use other apps • Free Laundry Room • Free Parking

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.

4.94 out of 5 average rating, 186 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.

4.9 out of 5 average rating, 365 reviews

The living room features a spacious teal sofa paired with a simple black coffee table in front. A window with sheer curtains allows natural light to fill the area, complemented by a floor lamp and potted plants. Hardwood floors add warmth to the room.

Apartment in Berwyn

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

The living room is bright and spacious, featuring a comfortable seating area with a sofa and two armchairs. A coffee table is centered on a plush area rug, while natural light enters through multiple windows adorned with light curtains. Decorative artwork complements the warm color scheme.

4.98 out of 5 average rating, 114 reviews

SuperHost and Super Location Central OP

4.98 Star Superhost rating for this ideal Centrally-located, light, bright, spacious 2 bedroom 1 bath 2nd floor unit in a beautifully updated vintage building! Central air and forced air heat, hardwood floors throughout. Wonderful floor plan to enjoy your stay while you are "in", Near public transportation when you want to "be on the go"! Designated work space, high speed WIFI and 1 parking space on premises. Deck off the kitchen for outdoor space. Keyless access. 1 King/ 1 Queen bed

4.91 out of 5 average rating, 452 reviews

A bright kitchen area features a round table with a red and white checkered tablecloth and four white chairs. A small sink and a gas stove are present, along with a refrigerator. Natural light filters through a window adorned with a red gingham curtain.

Apartment in Berwyn

Private apartment with retro vibe

December discount dates! Cozy 1 BR apartment with retro touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus brand new twin sofa bed, + 1 more twin available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left

A cozy bedroom is visible through an open doorway, featuring a king size bed with decorative pillows and a soft blanket. Three framed wall decorations are arranged above the headboard, while bedside lamps provide soft illumination, creating a restful and inviting atmosphere.

4.98 out of 5 average rating, 124 reviews

Cheerful Oak Park Apartment

Welcome to our lovely space, located above a unique piano restoration shop. Spacious and relaxing, with plenty to enjoy staying in, and 5-minutes walking distance to cafes, grocery, bars, restaurants, and more. The apartment is down the street from a Botanic Garden, and there is a nice arts district nearby. Easily accessible to downtown Oak Park and Chicago with nearby public transportation and expressway (downtown Chicago is about 25-35 min. drive, 35-45 min. by train).

A spacious living area features a modern sectional sofa in neutral tones. A sleek television is mounted on the wall opposite a minimalist coffee table. The adjoining dining area, visible through an archway, includes a round table with four chairs.

4.88 out of 5 average rating, 329 reviews

Home in Forest Park Upstairs.

In this cozy apartment you will have a functional kitchen, in unit laundry, fast WiFi connection and access to a back yard.. The property is located 30 minutes from O'Hara International Airport, 20 minutes from Downtown Chicago via I-290, and 40 minutes away from Midway Airport. Forest Park is a very safe, vibrant and diverse suburb of Chicago. You will be within walking distance of many different restaurants, boutiques, bars, parks, and public transit.

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.

4.98 out of 5 average rating, 240 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.

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.

4.88 out of 5 average rating, 306 reviews

Cosmopolitan Nest in Oak Park North Side

Whether visiting Oak Park's historic district or exploring the Windy City for the renowned museums and its nightlife, we welcome you into our home. You are guaranteed a peaceful stay in your own apartment with private entrance on the first floor in our single family home. We are a professional family who maintain a quiet residence. CTA public transportation just steps away.

Popular amenities for Oak Park apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

Apartment in Lower West Side

The living area is furnished with a gray sofa adorned with patterned cushions, positioned next to a natural wood coffee table. A potted plant and a decorative mirror enhance the space. Two windows allow natural light to brighten the room.

4.94 out of 5 average rating, 174 reviews

Cute, Clean, Cozy Apartment in Pilsen

The living area is furnished with a comfortable gray sofa and a glass coffee table, complemented by decorative pillows. A large wall art piece depicting a city skyline adds a modern touch. Natural light fills the space, enhanced by nearby windows and an indoor plant.

4.87 out of 5 average rating, 226 reviews

2 Bed Apartment | Convenient Access to Downtown

4.96 out of 5 average rating, 353 reviews

A cozy living area features a gray sofa adorned with patterned cushions, complemented by a light-colored coffee table. Wooden flooring adds warmth, and large windows are draped with sheer curtains, allowing natural light to brighten the space. A small workspace is visible in the corner.

Apartment in Cicero

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Superhost

A bright dining area features a round wooden table surrounded by six upholstered chairs. Natural light floods the space through large windows. An open doorway leads to a cozy living area, where a patterned sofa and a striped chair are positioned invitingly.

4.9 out of 5 average rating, 157 reviews

Large Renovated 1st FL Suite Forest Park/Oak Park

Apartment in Lincoln Square

A cozy sleeping area features a spacious bed adorned with white linens and decorative pillows in soft yellows and grays. Two bedside tables with lamps provide warm illumination, while a small clock is visible on one side. Natural light filters in through a nearby window.

4.89 out of 5 average rating, 307 reviews

Stylish & Modern 2 Bedroom Lincoln Square Condo

Superhost

A well-lit bathroom is presented, featuring a modern vanity with a sink and storage below. Towels are neatly arranged on a shelf, and a window allows natural light. A toilet is positioned adjacent to a towel rack, complemented by a stylish faucet.

Apartment in Berwyn

4.81 out of 5 average rating, 107 reviews

Private APT Near to Food/Shops/highway/Garage park

A dining area features a textured black table with a decorative plant at the center. In the background, an open living space is visible with natural light streaming through large windows, a spacious couch, and modern decor elements, creating a welcoming atmosphere.

4.98 out of 5 average rating, 44 reviews

Treetop Vista • Spacious Luxe Near DT Chi+Parking

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.

5 out of 5 average rating, 85 reviews

Studio Apartment in Oak Park

Private apartment rentals

5 out of 5 average rating, 75 reviews

A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.

Apartment in Chicago

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

4.95 out of 5 average rating, 150 reviews

A modern living area features a gray sofa facing a round marble coffee table. Behind, a built-in bookshelf holds various books. Natural light streams through multiple windows, illuminating a dining area with a round table and stylish chairs. Greenery adds a touch of nature.

Apartment in Lake View

Chic retreat near the best of Lakeview & Wrigley

A cozy living room features a comfortable sofa with decorative cushions, set against light-colored walls. A glass coffee table sits in the center, complemented by a small table with an art piece nearby. Natural light flows through a large window, enhancing the inviting space.

5 out of 5 average rating, 36 reviews

Serene One-Bedroom Apartment near Chicago

A modern living area features a light gray sectional sofa paired with a round coffee table at the center. Natural light enters through large windows dressed in sheer curtains. A tall indoor plant is placed in the corner, adding a touch of greenery to the space.

4.87 out of 5 average rating, 47 reviews

Luxurious Lifestyle

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.

4.99 out of 5 average rating, 71 reviews

Historic Hotspot: Downtown Oak Park w/parking spot

Apartment in Jefferson Park

A light-filled dining area features a wooden table surrounded by four chairs. A plush sofa is positioned nearby, offering a cozy option for relaxation. Large windows dressed in navy curtains provide a view of the outside, contributing to an open and inviting feel.

4.95 out of 5 average rating, 243 reviews

Entire 1st Floor Apt near O'Hare/ORD & Blue Line

An open-concept kitchen features a spacious island with seating and pendant lighting above. Sleek white cabinetry contrasts with dark wood accents, while natural light brightens the room. The flooring showcases rich wooden tones, adding warmth to the space. Decorative wall art provides a touch of personality.

4.91 out of 5 average rating, 82 reviews

Gorgeous Penthouse with Parking in Heart of Forest Park

Apartment in Melrose Park

A comfortable living area is presented with a light-colored sofa draped with a soft blanket. A wooden coffee table sits center stage on a patterned rug. Two decorative lamps illuminate the space, and a bookshelf with various books and a dartboard is positioned against the wall.

4.96 out of 5 average rating, 118 reviews

KNG+QN/1 free parking/18 min to O’hare & Allstate

Apartment rentals with a hot tub

5 out of 5 average rating, 15 reviews

Apartment in Grant Park

Luxe 67th Flr 2BR: Endless Lake Views, Top Skydeck

Apartment in East Rogers Park

An open-concept living and dining area is showcased with a gray sectional sofa and a wooden coffee table. A modern ceiling fan hangs above, and natural light fills the space. A dining table with six chairs is positioned nearby, adjacent to a sleek kitchen.

4.85 out of 5 average rating, 101 reviews

Spacious Beautiful Condo

4.92 out of 5 average rating, 25 reviews

Apartment in River West

Luxury 3BD Penthouse – Private Patio+Skyline Views

Apartment in Fulton Market

A bright and airy living area is filled with natural light from floor-to-ceiling windows, offering expansive city views. A plush sectional sofa is positioned on a soft area rug. Potted plants and a console with a television add to the inviting ambiance.

4.97 out of 5 average rating, 34 reviews

Skyline Oasis: City & Lake Views

4.97 out of 5 average rating, 39 reviews

Apartment in Wicker Park

Winter Escape 1 BR in Wicker Parl|1 FREE G Parking

4.97 out of 5 average rating, 148 reviews

The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.

Apartment in Dunning

Belmont Pleasures - hot tub / arcade gaming room

4.91 out of 5 average rating, 57 reviews

A private balcony features wooden decking and a wooden railing. Two black wicker chairs with cushions and a matching coffee table create a cozy seating area. Potted plants hang from the railing, and the surrounding neighborhood is visible in the background.

Apartment in Albany Park

2Bed 2Bath 15min to Wrigley with Parking& Balcony