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Condo vacation rentals in Oak Park

Find and book unique condos on Airbnb

Quick stats about condo rentals in Oak Park

  • Total vacation rentals

    Explore 10 vacation rentals in Oak Park

  • Nightly prices starting at

    Oak Park vacation rentals start at €79 per night before taxes and fees

  • Verified guest reviews

    Over 1,970 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Oak Park vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oak Park rentals

  • 4.8 Average rating

    Oak Park stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated condo rentals in Oak Park

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

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Guest favorite
A spacious living area features a large sectional sofa arranged around a modern coffee table. Artwork adorns the wall above, with soft lighting enhancing the ambiance. A patterned area rug adds texture to the hardwood floor, while natural light enters through the adjacent windows.
Condo in Downtown Chicago

Two Floor Luxury 3 Bedroom Condo in Old Town

Enjoy comfort, privacy, and elevated city living in this spacious three-bedroom, top-floor duplex apartment, located next door to The Sono Chicago in the heart of Old Town Chicago. Ideal for families, groups, or extended stays, this home offers generous space, abundant natural light, and a quiet retreat above the neighborhood. Spanning two levels on the top floor, the apartment features inviting living areas, a fully equipped kitchen, and three private outdoor decks, creating multiple spaces to

FamilyLocationWalkability

4.94 out of 5 average rating, 113 reviews
Superhost
A modern living area features a dark sofa facing a wall-mounted flat-screen TV. A wooden shelf with decorative items and a lamp is positioned beside a designated work space with a chair. Exposed brick walls complement the sleek kitchen area visible in the background.
Condo in Logan Square

Sunny Getaway Steps from Bucktown + Wicker Park

Enjoy a relaxing and chic experience steps aways from the lively, sought-after Wicker Park and Bucktown! Our home is on a quiet, tree-lined street with its own private walk-up entrance and FREE parking space. Public transportation is also very accessible. There are endless options of restaurants, bars, and shopping. The 606 trail is also steps away! We are centrally located which makes it easy and convenient to explore Chicago! Come make some memories for the weekend or as long as you'd like!

ValueLocationNearby

4.77 out of 5 average rating, 162 reviews
Top guest favorite
A cozy seating area features a green sectional sofa adorned with decorative pillows in various patterns. A small wooden coffee table sits at the center, topped with a book and a small plant. Exposed brick walls complement large windows dressed with dark curtains.
Condo in Wicker Park

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

LocationFamilyHospitality

4.98 out of 5 average rating, 171 reviews
Superhost
A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.
Condo in Little Italy

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

LocationFamilyAmenities

4.92 out of 5 average rating, 283 reviews
Guest favorite
Condo in West Side

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Luxury 4BR/2.5BA residence featuring 3 private bedrooms and an open-concept bonus room with a queen bed and full-size bunk beds—perfect for upscale families or executive groups. The spa-inspired primary suite offers a soaking tub and rain shower with multiple settings. Enjoy a modern kitchen, stylish living room with a 76” smart TV, and a large covered patio. Located near UIC, West Loop, Chinatown, McCormick Place, the lakefront, and some of Chicago’s best dining and cultural attractions.

FamilyLocationView

4.93 out of 5 average rating, 178 reviews
Guest favorite
A modern living area features a blue sectional sofa facing a mounted flat-screen TV. A wooden coffee table is positioned in front of the sofa. A desk and chair are situated near a large window, allowing natural light to brighten the room.
Condo in Irving Park

Newly updated 1BD/1B in Old Irving Chicago!

Welcome to your home away from home in the heart of one of Chicago's safest and quietest neighborhoods! This beautifully updated 1 bedroom apartment offers everything you need for a comfortable and convenient stay. It is perfect for couples, solo travelers, and business visitors. Book now for a truly unforgettable experience in the Windy City! - 1 free parking spot - 400 MB Wifi - 2 smart T.V. with access to Netflix, Hulu, Amazon and more! - Desk - Easy app paid laundry in the building.

ValueLocationNearby

4.87 out of 5 average rating, 167 reviews
Guest favorite
The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.
Condo in North Side

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

ValueFamilyCondition

4.95 out of 5 average rating, 175 reviews
Guest favorite
A spacious living room features a comfortable couch with assorted pillows, a wooden coffee table, and an area rug. Large windows allow natural light to fill the room, accompanied by a ceiling fan and an entertainment unit. A decorative floor lamp and wall decor enhance the inviting space.
Condo in North Side

Susie's Space. 2BR easy parking & pet friendly

Sunny and spacious, 2 bedroom apartment in Avondale near the Green Exchange/ Greenhouse Loft Flexible, self check-in Easy street parking (with provided permits) Pet fee $80 per pet Bedroom 1 with a king sized bed Bedroom 2 with a full bed Air conditioning and ceiling fans Soft linens and towels Separate dining room Fully equipped kitchen Free WIFI Smart TV for streaming Garden in back with a fire pit and charcoal grill Laundry room in basement

FamilyLocationBathroom

4.92 out of 5 average rating, 396 reviews
Superhost
Condo in Ukrainian Village

Modern Chicago Movie Themed Apt

Welcome to Chicago at the Movies! An amazing fully updated apartment in the Ukrainian Village neighborhood. This midcentury modern 3 bedroom home is perfect for groups, couples, and families looking for a perfect Chicago vacation. The property is conveniently located on Grand Avenue just minutes by car, bus or train from Downtown and the Lakefront. We are also just a short 5 Minute ride to the United Center for concerts sports and more!

ValueLocationWifi

4.88 out of 5 average rating, 229 reviews
Superhost
A vibrant living area is highlighted by a deep blue sofa and a colorful area rug. A large wall-mounted television is positioned across from the seating, and modern artwork decorates the walls. The adjoining kitchen is visible in the background, showcasing sleek cabinetry and new appliances.
Condo in Humboldt Park

3D Tour! Designer Condo near Logan Square

Scan QR code in photos for a 3D Tour! What you’ll love: - Totally renovated garden unit, completed in 2021. Everything new. - Upscale furnishings & decor. - Gourmet, fully equipped kitchen w/ new appliances, coffee maker and spices. - Remote work station w/ super fast Wi-Fi (600mb). - Serta queen mattress in master. - Bunk beds w/ full and twin sized memory foam mattresses. - Heat & A/C.

FamilyLocationHospitality

4.85 out of 5 average rating, 284 reviews
Top guest favorite
A bright living room features large windows allowing natural light to fill the space. Comfortable seating includes a spacious couch and decorative poufs. A smart TV is mounted on the wall, and plants bring a touch of greenery, enhancing the relaxing environment.
Condo in North Side

Designer Avondale 2BR w/Easy Parking

Experience the Avondale Retreat, a sun-filled, stylish Chicago apartment perfect for couples or friends. This impeccably clean, first-floor space offers a comfortable layout, abundant natural light, and free street parking. Enjoy a full kitchen, two tranquil bedrooms with Parachute linens, a dedicated workspace, and fast Wi-Fi. Ideal for 2-4 guests seeking a relaxing base to explore the city.

ValueFamilyTV

4.99 out of 5 average rating, 165 reviews
Superhost
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

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!

FamilyLocationParking

4.79 out of 5 average rating, 394 reviews

Popular amenities for Oak Park condo rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly condo rentals

Top guest favorite
Condo in Wicker Park

Two Bedroom w Porch in Wicker Park

FamilyValueBathroom

4.96 out of 5 average rating, 123 reviews
Top guest favorite
A spacious living area displays hardwood floors and elevated ceilings. A large flat-screen TV is mounted above a decorative brick fireplace. Natural light filters through multiple windows, illuminating the contemporary furniture arrangement that includes a soft sectional sofa and accent chair.
Condo in Lincoln Park

1,800ft² Parking Workspace W/D Full Kitch

FamilyValueCheck-in

4.99 out of 5 average rating, 223 reviews
Guest favorite
A spacious living room features floor-to-ceiling windows that allow ample natural light, showcasing views of the city. A large gray sectional sofa is complemented by a cozy yellow armchair. A wall-mounted television is situated above a built-in fireplace, with a private balcony visible through sliding doors.
Condo in West Town

Your perfect place looks like?

LocationValueWalkability

4.93 out of 5 average rating, 181 reviews
Superhost
The living area features a sectional couch with an accompanying throw pillow, positioned on a patterned area rug. A full-length mirror enhances the space, while a wall-mounted flat-screen TV is visible. Two chairs add to the seating arrangement, complemented by warm-toned wooden flooring.
Condo in West Town

3 BR Sleek Minimalist Centrally Located Unit

FamilyLocationParking

4.89 out of 5 average rating, 193 reviews
Guest favorite
A spacious living area with large windows allows natural light to fill the room. A light-colored sectional sofa is complemented by two blue armchairs and a round coffee table. A neutral area rug anchors the space, creating a comfortable environment for relaxation.
Condo in East Rogers Park

Alluring Condo w/ Pri. Prkng Cls to Transit &Beach

LocationValueWalkability

4.82 out of 5 average rating, 216 reviews
Top guest favorite
A living area showcases a wooden entertainment center with a TV, flanked by a decorative console table and two lamps. The space features hardwood floors and a neutral color palette, complemented by a circular wall mirror. A staircase in the background leads to the upper level.
Condo in Clarendon Hills

Apartment in Clarendon Hills.

LocationValueAccess

5.0 out of 5 average rating, 138 reviews
Top guest favorite
The historic greystone facade is prominently displayed, featuring elegant architectural details. A wrought-iron fence surrounds the property, with vibrant pink flowers blooming in the foreground. Large windows allow natural light to illuminate the inviting entrance.
Condo in Wrigleyville

Wrigleyville Inn. Historic Greystone. Parking pass

LocationFamilyKitchen

4.98 out of 5 average rating, 181 reviews
Top guest favorite
An open kitchen and dining area features exposed wooden beams and stylish light fixtures. A modern dining table with black chairs provides seating, while a lounge chair is positioned nearby. Decorative plants and art add warmth to the contemporary space.
Condo in Wicker Park

Modern Izakaya Studio in Wicker Park

ValueFamilyKitchen

4.96 out of 5 average rating, 159 reviews

Pet-friendly condo rentals

Guest favorite
The living area features a mix of modern and industrial design, with exposed brick walls and hardwood flooring. A cozy sectional sofa, accented by colorful pillows, complements a stylish area rug. A kitchen area with dark cabinetry and stainless-steel appliances is visible in the background.
Condo in Wrigleyville

Can't Beat This 2min Walk to Wrigley!

LocationValueAccuracy

4.81 out of 5 average rating, 290 reviews
Top guest favorite
A comfortable living room is showcased with a grey sofa adorned with decorative pillows. A round coffee table sits on a patterned rug, and a green vintage cabinet adds a pop of color. Bright light enters through open doorways, leading to a dining area beyond.
Condo in Downtown Chicago

Large Remodeled Home in Lincoln Park, Sleeps 12!

LocationFamilyAccess

4.97 out of 5 average rating, 150 reviews
Top guest favorite
The living area features a spacious couch accompanied by two armchairs, all positioned around a circular dining table. A large window allows natural light to illuminate the space, adorned with potted plants and modern artwork that adds a touch of style.
Condo in Ukrainian Village

Ukrainian Village 3BR/3BA • Private Patio, Parking

LocationFamilyLaundry

4.98 out of 5 average rating, 128 reviews
Guest favorite
The living room features a wall-mounted television above a wooden console, surrounded by decor and framed photos. Comfortable seating includes gray armchairs and a sectional sofa, offering a relaxed setting. Natural light brightens the space through nearby windows, enhancing the airy atmosphere.
Condo in West Town

Chicago River West 4 Bedroom / 3 Bathroom

FamilyValueTV

4.81 out of 5 average rating, 264 reviews
Top guest favorite
A modern living space features a sleek kitchen island with a sink, surrounded by light wood flooring. Large windows invite natural light, illuminating a comfortable gray sofa and a dining table with black chairs. A vibrant wall art piece adds color to the room.
Condo in Lincoln Park

NEW luxury Old Town 1-Bedroom condo

LocationValueKitchen

4.95 out of 5 average rating, 151 reviews
Top guest favorite
A bright living area is showcased with large windows allowing natural light. Red and orange artwork adorns the walls, while a gray ottoman centers the room. Seating consists of a gray sofa and an armchair with a geometric pattern, accompanied by decorative lamps on either side.
Condo in Ravenswood

Lincoln Square Gem!

FamilyValueLaundry

4.97 out of 5 average rating, 509 reviews
Superhost
A modern living area is presented with large windows allowing ample natural light. A navy sofa sits beside a decorative coffee table on a patterned rug, with a stylish mirror and television mounted on the wall. The space features sleek wooden accents for a contemporary feel.
Condo in West Side

816 PLZN LUX Apartment | Rooftop | Garage Parking

LocationFamilyComfort

4.81 out of 5 average rating, 176 reviews
Guest favorite
A modern multi-story building is nestled among leafy trees, featuring large windows and a sleek, minimalistic design. A wooden staircase leads to the entrance, while blooming flowers add a touch of color to the landscaped garden in front.
Condo in Evanston

Spacious Evanston Unit - Walk to Northwestern U

FamilyLocationKitchen

4.78 out of 5 average rating, 723 reviews

Condo rentals with a pool

Top guest favorite
An open-concept living area features large windows that invite natural light and provide a view of the cityscape. A comfortable blue sofa is adorned with patterned pillows, while a light wood coffee table sits in front of it. A dining space with black chairs complements the modern kitchen.
Condo in Evanston

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

FamilyValueAccess

4.96 out of 5 average rating, 142 reviews
Guest favorite
The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.
Condo in Elk Grove Village

Just remodeled apartment close to airport and mall

ValueFamilyHospitality

4.91 out of 5 average rating, 128 reviews
Superhost
A comfortable living area features a dark sofa, coffee table, and a modern TV stand with a large television. A dedicated dining space with a round table for two is visible. Sliding glass doors lead to a private balcony, providing natural light and outdoor views.
Condo in Lombard

Pond View, Washer Dryer, Non Smoking, Pet Free

LocationValueLaundry

4.88 out of 5 average rating, 58 reviews
Guest favorite
Condo in Berwyn

Red Door

LocationIndoor spacesHospitality

5.0 out of 5 average rating, 13 reviewsA clear swimming pool is surrounded by a spacious deck featuring white lounge chairs. A fence provides privacy, and lush greenery is visible in the background, complementing the bright blue sky above.
Private room in Westchester

Lovely 2 Bed 2 Bathroom!

Guest favorite
Condo in Evanston

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

FamilyLocationEV charging

4.96 out of 5 average rating, 123 reviews
Guest favorite
An open-concept living space is showcased, featuring modern kitchen appliances, a dining table with seating for six, and a comfortable sofa. Large windows allow natural light to fill the area, providing views of the outdoor landscape.
Condo in Evanston

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

FamilyValueBeach

4.96 out of 5 average rating, 123 reviews
Guest favorite
The living area features a sectional sofa adorned with vibrant cushions beside a coffee table. Natural light filters through large windows dressed with horizontal blinds, illuminating a console with a flat-screen TV and decorative accents.
Condo in Evanston

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

LocationValueCheckout

4.96 out of 5 average rating, 147 reviews

Destinations to explore