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Condo vacation rentals in Chicago

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Top-rated condo rentals in Chicago

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A bright living room features a spacious red sectional sofa, centered around a glass coffee table on a patterned area rug. Natural light streams through large windows, enhancing the clean lines of the decorative fireplace and the modern accent chair nearby.

Condo in Uptown

4.92 out of 5 average rating, 167 reviews

Stunning, Spacious, & Sunny 2bed 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 Wilson Red Line, this location is excellent for exploring all that Chicago has to offer.

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

4.94 out of 5 average rating, 214 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.

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 Mayfair

4.88 out of 5 average rating, 131 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.

Top guest favorite

An elegantly furnished dining area features a wooden table with a textured runner. Dark leather chairs surround the table, and a modern chandelier hangs above. The open kitchen, equipped with stainless steel appliances and bar seating, is visible in the background.

Condo in Logan Square

4.98 out of 5 average rating, 281 reviews

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Luxurious 1BR/2BA garden-level condo in vibrant Logan Square! Comfortably furnished with tons of light and amenities, conveniently located one block from the Logan Square Blue Line Station and located on a quiet street. Steps from all of the hip restaurants and nightlife in Logan Square. Huge back yard and patio with fire pit for guest use. Free on-site garage parking with remote. And, if using public transit, the Logan Square is 8 stops, ~15-20 minutes from the Loop downtown!

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 East Rogers Park

4.93 out of 5 average rating, 248 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.

A bright studio apartment features large windows allowing natural light to fill the space. A cozy bed is positioned beside a small dining table and chairs, while a comfortable sofa is present for relaxing. A television is mounted on the wall for entertainment.

Condo in River West

4.78 out of 5 average rating, 194 reviews

Cabin 301 at 747 Lofts

This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away!

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

4.96 out of 5 average rating, 113 reviews

Modern Izakaya Studio in Wicker Park

Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

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 Hermosa

4.84 out of 5 average rating, 207 reviews

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.

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, 111 reviews

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

Urban-Luxe experience at the Bliss of Evanston Condo. Elegant finishes and a sweeping Sky Terrace view of downtown Evanston. Resort-like amenities with fitness center, outdoor pool, free parking in indoor GAR, biz ctr, and much more. 2 bedrooms, 2 full baths, 2 roll-out beds welcome you to a comfortable stay near Northwestern University, Loyola, and Kellogg and minutes from Chicago Downtown.

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

4.77 out of 5 average rating, 647 reviews

Spacious Evanston Unit - Walk to Northwestern U

Welcome to my contemporary and spacious garden level unit located on a tree filled, serene residential block in Evanston. Walking distance to Northwestern University, retail areas, trains, golf, and the lovely beaches of Lake Michigan! A Walgreens and a local brewery restaurant are just a few steps away. Plentiful free street parking and free EV chargers one block away.

A spacious living area showcases a light-colored sofa paired with dark green accent chairs. A glass coffee table sits atop a patterned rug, while decorative elements, including candles and potted plants, are arranged on a wall shelf. Natural light enters through large windows.

Condo in Bucktown

4.93 out of 5 average rating, 106 reviews

Wicker Park/Bucktown condo with large balcony

This freshly remodeled condo with European flair is set in the trendy yet peaceful neighborhood of Bucktown - a perfect base for exploring Chicago. A short walking distance to 2 Blue line CTA stops (Western and Damen), it is surrounded by quaint neighborhood bars, restaurants, and coffee shops as well as grocery stores and trendy shopping.

Natural light fills the open living space, highlighting the modern decor. A large island with seating offers a gathering place, while stylish pendant lights hang above. Large windows reveal views of greenery outside, and a glass door leads to an outdoor balcony. Soft furnishings add comfort.

Condo in North Side

4.96 out of 5 average rating, 346 reviews

Beautifully Renovated 2BR in Historic Lincoln Park

In the heart of Lincoln Park's historic Arlington-Deming neighborhood and its tree-lined streets, this 3rd floor walkup is close to everything -- Lake Michigan, transportation, dining, nightlife, parks, and more! The recently renovated condo is perfect for families, with a large master suite and twin/full bunk in the second room.

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Popular amenities for Chicago condo rentals

Free parking on premises

Air conditioning

Condo rentals with a pool

An outdoor pool area is shown, featuring a clear blue pool surrounded by lounge chairs. Trees provide a touch of greenery, while a modern glass structure offers shaded seating. Sunshine reflects off the water, creating a bright and inviting atmosphere.

Condo in Evanston

4.96 out of 5 average rating, 98 reviews

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

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

4.82 out of 5 average rating, 60 reviews

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

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

4.93 out of 5 average rating, 87 reviews

Just remodeled apartment close to airport and mall

An outdoor swimming pool is surrounded by lounge chairs, offering a relaxing space. Trees are strategically placed around the area, and large glass walls provide views to the inside. Sunlight reflects off the water, enhancing the serene setting.

Condo in Evanston

4.91 out of 5 average rating, 128 reviews

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

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

4.91 out of 5 average rating, 47 reviews

Pond View, Washer Dryer, Non Smoking Community

Condo in Evanston

4.96 out of 5 average rating, 104 reviews

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

A light-filled living area features a comfortable beige sofa adorned with decorative pillows. A coffee table sits in front, holding a plant and tray. In the background, a kitchen with wooden cabinets and bar stools is visible, complementing the modern aesthetic.

Condo in Downers Grove

4.87 out of 5 average rating, 55 reviews

Upscale, Smoke and Pet Free, Washer Dryer, Balcony

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

4.94 out of 5 average rating, 48 reviews

Pond View, Washer Dryer, Non Smoking, Pet Free

Condo rentals with a hot tub

A well-lit living space features large windows allowing natural light. A green sofa and two white chairs are arranged around a circular coffee table. A round dining table with wooden chairs is positioned nearby, and a soft area rug adds warmth to the hardwood floor.

Condo in Lake View

4.79 out of 5 average rating, 170 reviews

Modern Wrigley Oasis with Parking!

A serene bedroom is illuminated by soft purple lighting. A spacious bed with a polka dot blanket is centered in the room. Floor-to-ceiling glass doors reveal a view of a vibrant city skyline at night, with city lights twinkling in the background.

Condo in River North

4.26 out of 5 average rating, 19 reviews

voco: Balcony & City View

A rooftop space features a hot tub illuminated in blue, accompanied by a seating area with a sofa. A city skyline stretches in the background, showcasing a vibrant urban landscape against the night sky.

Condo in Wicker Park

4.92 out of 5 average rating, 38 reviews

Luxe condo w/ HOT TUB and Amazing Roof Deck!

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 West Town

4.97 out of 5 average rating, 151 reviews

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

A small balcony is visible, featuring a round table with two chairs and a planter containing flowers. The balcony is bordered by a metal railing, with trees and the street below providing a backdrop, allowing natural light to fill the space.

Condo in Uptown

4.89 out of 5 average rating, 9 reviews

Bright and Beautiful Penthouse - Close to the lake

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

A cozy living area is furnished with a beige sofa and two blue armchairs arranged around a wooden coffee table. Natural light enters through multiple windows adorned with blinds. A large area rug adds warmth, while a wall art piece enhances the space's character.

Condo in Lincoln Square

4.71 out of 5 average rating, 7 reviews

Lincoln Square Retreat

An indoor spa area features a hot tub with bubbling water and sleek, modern design elements. Gray stone walls and floors create a clean ambiance. A large wall-mounted television is present, alongside private showers and a wooden bench nearby, offering a space for relaxation.

Condo in Oak Lawn

Best view and luxury style, Located in Downtown

Weekly condo rentals

Top guest favorite

A bright living space featuring a plush sectional sofa positioned around a coffee table. Artful cityscape images adorn the walls, complemented by vibrant green paint and natural light streaming through large windows. A dining area with a contemporary table offers additional seating for gatherings.

Condo in Lake View

4.95 out of 5 average rating, 61 reviews

2BR Apt, Office, Parking & Backyard by Wrigley

A living room space features a soft velvet sofa in teal color, accompanied by a matching ottoman. A wooden coffee table sits on a patterned area rug, with a plant placed in a terracotta pot nearby. Wall art is displayed above the sofa, enhancing the area.

Condo in Chicago

4.93 out of 5 average rating, 73 reviews

Urban Oasis Getaway. 6 stops to downtown!

Top guest favorite

An outdoor terrace features green foliage along the railing, enhancing the space's natural feel. Two comfortable chairs surround a wooden table, creating an inviting area for relaxation. A patterned rug adds texture, with wide views of the surrounding trees and clear sky in the background.

Condo in Skokie

4.98 out of 5 average rating, 41 reviews

Free Parking Balcony, Weekly 5% & Monthly 20% Off

The studio apartment features a spacious open layout with a comfortable bed, muted bedding, and a nightstand. A TV is positioned on a modern media unit, and a mini fridge adds convenience. Natural light filters in through a window, illuminating the neutral decor.

Condo in Magnificent Mile

4.7 out of 5 average rating, 234 reviews

Studio flat in the heart of Chicago's Gold Coast

Top guest favorite

A well-designed living room features a large arched window that allows natural light to brighten the space. Two armchairs and a small table are positioned near the window, while a cozy beige sofa is adorned with a soft blanket. Green plants add a touch of nature.

Condo in West Town

5 out of 5 average rating, 59 reviews

Sun-Soaked West Loop Penthouse/Private Rooftop/3BA

Top guest favorite

A lush garden area showcases a variety of blooming flowers surrounded by greenery. The path is lined with vibrant floral colors leading up to the brick building, which features large windows allowing natural light to fill the space.

Condo in East Rogers Park

4.97 out of 5 average rating, 63 reviews

Jarvis Gardens - 1BR/BEACH/Wine patio/fire pit

The living room features a large, L-shaped gray sofa, complemented by two black leather massage chairs. A wooden coffee table sits in the center, and large windows with vertical blinds allow natural light to fill the space, accentuated by an orange-painted wall.

Condo in Garfield Ridge

4.77 out of 5 average rating, 22 reviews

1st Floor Condo Apartment Close to Midway Airport

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 Tri-Taylor

5 out of 5 average rating, 33 reviews

Quick Drive to Downtown Chicago & Early Check-In

Quick stats about condo rentals in Chicago

Total rentals
1K properties
Nightly prices starting at
G$4,184 GYD before taxes and fees
Total number of reviews
70K reviews
Family-friendly rentals
630 properties are a good fit for families
Pet-friendly rentals
300 properties allow pets
Rentals with a pool
80 properties have a pool

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