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Condo vacation rentals in West Side

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Top-rated condo rentals in West Side

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Top guest favorite
A cozy living space features a vibrant orange sofa complemented by decorative throw pillows. A dining area with a small table stands beside a fully equipped kitchen. Artwork adorns the walls, while natural light streams through windows, enhancing the inviting atmosphere.
Condo in Chicago
4.98 out of 5 average rating, 109 reviews

Chic & Comfy • Close to Wrigley

Welcome to your comfy, cozy, cheerful hideaway in the beautiful Buena Park!☀️ Buena Park is a little-known gem. Our home is just blocks from the lakefront (4 blocks), Wrigley (6 blocks), and the major L-line in Chicago (1 block)...yet, you'd never know it given how peaceful and serene it is! We live here part-time, so rest assured you'll have everything you need for a comfortable and enjoyable stay. We ask you please respect our place, and that you enjoy the trinkets + personal items we have!

Guest favorite
The living room features a bright layout with large windows allowing natural light to flood the space. A red sectional sofa invites relaxation, complemented by a round coffee table. A decorative fireplace is positioned beneath a wall art piece, enhancing the room's charm.
Condo in Chicago
4.92 out of 5 average rating, 178 reviews

Vibrant, Sunny & Spacious 2 bd 1 ba Uptown Condo

Welcome to your home away from home in Uptown! My bright and inviting condo offers a perfect blend of comfort and convenience, with your own sunny living room to relax, fully-equipped kitchen and formal dining room, spacious private bedroom, serene sunroom with full bed for extra guests, and a workspace for business travelers. Short walk from the lakefront and Montrose Beach, and a 6-minute walk to the 24/7 Wilson Red Line, this location is excellent for exploring all that Chicago has to offer.

Guest favorite
A spacious living area is showcased, featuring a light-colored sectional sofa and a round coffee table. A ceiling fan is installed above, and natural light fills the room through large windows. The adjoining staircase leads to an upper level, complementing the open layout.
Condo in Chicago
4.88 out of 5 average rating, 179 reviews

Tri-Taylor/Medical Dist. near West Loop

Enjoy this stylish Newly Rehabbed condo equipped with 3 bedrooms and 2 bathrooms. Modern kitchen with stainless steel appliances. ~UNITED CENTER home of the Chicago Bulls and Blackhawks located within 2-3 min walk *2 blocks*. 4-7 min drive to little Italy restaurants/Tri Taylor/Medical District. Near Downtown (5-7min drive). 2 Blocks from the blue line ~Free street parking ~Washer Dryer ~Dishwasher ~spacious Back patio Parties are restricted due to COVID guidelines for the city of Chicago.

Guest favorite
The living area showcases a spacious layout, featuring a comfortable couch, a modern glass coffee table, and a stylish armchair. Natural light floods the room through large windows, accentuated by hardwood flooring and a decorative rug. A dining table for four is positioned nearby, along with a colorful wall art.
Condo in Chicago
4.91 out of 5 average rating, 127 reviews

WONDERFUL WICKER PARK 2BD/2BA w/ patios +parking

Escape into this spacious condo in a bustling top-notch, Chicago neighborhood! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - 2 private walk-out patios! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out patio - Designated parking spot! - Steps away from blue line Damen station (800 feet)

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 Chicago
4.96 out of 5 average rating, 132 reviews

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

BEST LOCATION IN LOGAN SQUARE/AVONDALE with garage parking! 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.

Top guest favorite
The living area features exposed brick walls and hardwood floors, with an arrangement of seating including a red armchair and a cozy sofa. A glass coffee table sits on a plush area rug. A wall-mounted flat-screen TV is present, alongside indoor plants and decorative elements.
Condo in Chicago
4.99 out of 5 average rating, 302 reviews

❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

• 1,750ft² / 162m² . My home is on the second floor of a four flat Itallian Brick Building . You have 2 flight of stairs to Climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport fireplace is not operational.

Guest favorite
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 Chicago
4.94 out of 5 average rating, 230 reviews

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.

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 Chicago
4.87 out of 5 average rating, 140 reviews

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.

Guest favorite
An outdoor patio is showcased, featuring a rectangular fire table surrounded by four cushioned chairs. The wooden decking contrasts with the subdued colors of the furniture. A partial cover is draped over one corner, providing shade from the sun.
Condo in Chicago
4.97 out of 5 average rating, 161 reviews

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Explore Chicago's charm just moments from downtown! This Airbnb boasts a spa bath with a luxurious rain shower and jetted tub, a fully equipped kitchen for culinary adventures, comfortable reclining sofas for relaxation, and ample space to unwind. Sleep like royalty in the master bedroom's king bed, and a queen murphy bed in the living area ensures a comfortable stay for up to four guests. Step outside to the patio with a fire pit for cozy evenings. Your Windy City getaway begins here!

Guest favorite
A well-lit living area features a striped sofa accompanied by two modern armchairs. A wooden coffee table sits in the center, complemented by a patterned rug. Shelves display an array of silverware and decorative items, adding character and visual interest to the space.
Condo in Chicago
4.93 out of 5 average rating, 265 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This cozy AirBnb is perfectly situated. A beautifully clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation & restaurants, red line "El" trains & bus routes. Apt has private, queen bedroom, en suite full bathroom, living room w/queen sofa bed, TV, dining table, & partial kitchenette. NOTE: No full kitchen.

Superhost
A living area features a leather sofa and two upholstered chairs, arranged around a glass coffee table. A brick accent wall provides character, while a large television sits atop a wooden console. Artworks adorn the walls, accompanied by natural light from the windows.
Condo in Chicago
4.78 out of 5 average rating, 278 reviews

Logan Square Beauty with 2 Bedrooms W/parking

Our two-bedroom condo is beautifully appointed and has vintage charm everywhere you look. You'll have access to a shared backyard, and all of the amenities of home - while being a 10 minute walk from some of the hottest bars and restaurants in Chicago. One garage parking spot is available during your stay. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea!

Guest favorite
The living area features a plush, gray sofa paired with a deep blue accent chair. A light-colored coffee table rests on a patterned rug, while warm lighting is provided by wall-mounted fixtures. A small bookshelf and decorative items add a personal touch to the space.
Condo in Chicago
4.84 out of 5 average rating, 364 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of amenities. Just a block from everything this neighborhood has to offer and 2 blocks from the 'L' to take you downtown or to O'hare Airport. Premium location to effortlessly walk from our quiet side street and be in the heart of all the entertainment! I provide all the essentials to make your stay easy and comfortable!

Popular amenities for West Side condo rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Weekly condo rentals

Top guest favorite
Condo in Chicago
4.99 out of 5 average rating, 177 reviews

Christmas in the City- Holiday Duplex in Lakeview

Top guest favorite
A charming front porch features a small round table surrounded by two wrought iron chairs. A cozy seating area is adorned with a vibrant red blanket. Flower planters filled with lush greenery and colorful blooms enhance the inviting ambiance, with sunlight filtering through the trees.
Condo in Chicago
4.96 out of 5 average rating, 137 reviews

Best Lincoln Square location. Spacious 2 bedroom

Guest favorite
A bedroom features a spacious bed dressed in deep blue linens, complemented by decorative pillows. The walls are painted in a rich blue, accented by round mirrors. Two bedside lamps illuminate the space, while a patterned area rug lies on the hardwood floor.
Condo in Oak Park
4.93 out of 5 average rating, 280 reviews

Picture Perfect 3Bed Steps from Train and FLW

Guest favorite
A spacious bedroom is equipped with a large bed featuring decorative pillows. On either side of the bed, warm lamps provide soft lighting. Above the bed, two framed art pieces display botanical themes, adding a touch of nature to the decor. A neutral-colored bench is placed at the foot of the bed.
Condo in Chicago
4.94 out of 5 average rating, 142 reviews

The Urban Oasis | Outdoor Lounge • Sleeps 10+

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 Chicago
4.95 out of 5 average rating, 112 reviews

NEW luxury Old Town 1-Bedroom condo

Top guest favorite
A welcoming living room features a light beige sectional sofa adorned with decorative pillows. A round wooden coffee table occupies the center, complemented by a soft area rug. Large windows allow natural light to fill the space, and a ceiling fan adds a modern touch.
Condo in Chicago
5 out of 5 average rating, 43 reviews

Quick Drive to Downtown Chicago & Early Check-In

Guest favorite
The living room features hardwood flooring and is illuminated by natural light streaming through large bay windows. Two comfortable sofas face a coffee table, with a TV mounted on a console unit nearby. A warm and inviting atmosphere is created by the arrangement and decor.
Condo in Chicago
4.88 out of 5 average rating, 33 reviews

Comfy and Walkable

Guest favorite
A bright bedroom features a cozy yellow bedspread draped over a spacious bed. A light-colored dresser stands against the wall, adorned with subtle decorative details. Soft lamp light creates a warm ambiance, while artwork adds a touch of color to the room.
Condo in Chicago
4.82 out of 5 average rating, 51 reviews

Cozy Kitties in the City 1BR by Park/Sox/Transit

Pet-friendly condo rentals

Guest favorite
A living area features two tufted gray sofas and a glass coffee table atop a patterned rug. The space is illuminated by natural light from large windows, with decorative accents including throw pillows and a cozy ottoman.
Condo in Chicago
4.84 out of 5 average rating, 382 reviews

Chic and Charming Vintage Condominium in Lincoln Park

Top guest favorite
A comfortable living area features an orange sofa and a variety of artwork on the walls. A round coffee table sits in the center of a patterned area rug. Natural light filters through the window shades, enhancing the welcoming vibe of the space.
Condo in Chicago
4.95 out of 5 average rating, 106 reviews

Spacious 3BR • Great for Groups • Fast WiFi • Pets

Superhost
A modern living area is presented with a dark gray sofa adorned with neutral pillows and a cozy throw. A round mirror reflects light, while a white coffee table with a decorative plant sits centered on a plush area rug, enhancing the room's inviting atmosphere.
Condo in Chicago
4.82 out of 5 average rating, 183 reviews

Charming Condo near U.C./Loop/McCormick Place

Guest favorite
A bright living area is illustrated with large windows allowing natural light to fill the space. A comfortable beige sectional sofa provides seating, while a wooden coffee table sits on an area rug. A desk with modern design and a chair are present, enhancing the workspace.
Condo in Chicago
4.93 out of 5 average rating, 141 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

Superhost
A spacious living area is shown, featuring a large sectional sofa with decorative pillows. A glass coffee table occupies the center of the room, while a television sits on a wooden stand. The kitchen is visible in the background, with modern appliances and a dining area.
Condo in Chicago
4.9 out of 5 average rating, 101 reviews

Spacious 5-BR Apt next to transit Free Parking

Guest favorite
A modern living area features a spacious couch with a textured throw, positioned near a wall-mounted TV above a sleek fireplace. Large sliding glass doors lead to an outdoor patio, revealing a view of the vibrant neighborhood.
Condo in Chicago
4.98 out of 5 average rating, 132 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

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 Chicago
4.92 out of 5 average rating, 370 reviews

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

Top guest favorite
A vibrant seating area is showcased with a blue couch adorned with colorful throw pillows and a brown leather sofa. A small black coffee table rests on a patterned area rug, which features geometric designs. Large windows allow natural light to fill the space.
Condo in Chicago
4.98 out of 5 average rating, 131 reviews

Steps from the Lake, Lovely 3-Bedroom Condo

Condo rentals with a pool

Guest favorite
The living area features a comfortable sofa adorned with patterned cushions, accompanied by a stylish coffee table. A modern dining setup is visible in the background, along with sleek kitchen cabinetry. Light from overhead fixtures illuminates the open layout with dark hardwood flooring.
Condo in Evanston
4.96 out of 5 average rating, 104 reviews

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

Guest favorite
A bright living area features large windows that offer city views. Comfortable seating arrangements include a pair of teal sofas and a wooden armchair. A coffee table sits at the center on a soft area rug, accompanied by a flat-screen TV mounted on a nearby wall.
Condo in Evanston
4.95 out of 5 average rating, 119 reviews

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

Superhost
A cozy living area is highlighted by a wood-burning fireplace, where a warm fire flickers. A sleek coffee table sits in front of a comfortable sectional sofa, complemented by a textured area rug. Two glasses of wine rest atop the table, adding a touch of relaxation.
Condo in Lombard
4.83 out of 5 average rating, 65 reviews

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

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
4.92 out of 5 average rating, 96 reviews

Just remodeled apartment close to airport and mall

Guest favorite
A dining area is presented with a sleek table surrounded by four black chairs. A grey sectional sofa is positioned nearby, complemented by a modern floor lamp. Large windows provide natural light, and a vibrant cityscape photo adorns the wall.
Condo in Evanston
4.92 out of 5 average rating, 134 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Superhost
A cozy living area features a sectional sofa adorned with pillows and a throw pillow inscribed with 'Enjoy.' A round coffee table holds decorative items, while framed art showcases serene designs on the wall. A small dining area is visible in the background.
Condo in Lombard
4.92 out of 5 average rating, 49 reviews

Pond View, Washer Dryer, Non Smoking Community

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
4.96 out of 5 average rating, 109 reviews

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

A modern living area is revealed with large windows showcasing views of the lake and boats. A light-colored sofa and armchair are arranged around a glass coffee table, complemented by a floor lamp and a large TV mounted against a neutral wall.
Condo in Burbank

Iconic Style, Charming Lake View

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