Condo holiday rentals in Chicago

4.92 out of 5 average rating, 189 reviews

Condo in Uptown

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.

4.94 out of 5 average rating, 143 reviews

The living room features a comfortable sectional sofa adorned with accent pillows, positioned in front of a large television. A striking wall mural depicting Earth adds character. Natural light streams through expansive windows, illuminating a round coffee table atop a soft area rug.

Condo in West Town

10 Min Downtown Free Parking Ping-Pong Sleeps 10

ONE FREE INDOOR & SAFE PARKING SPOT INCLUDED! The building is next to a bus stop that brings you right into downtown! You would enjoy staying in the spacious 1800 sq ft with 10 ft high ceilings. 2 bedroom/2 bathroom apartment with ZERO STAIRS to get inside! It is an excellent solution for elder people and families with kids or maybe just a group of friends coming to have fun at the UNITED CENTER sports event or tourists as well as business folks or doctors to attend McCormick Place conferences.

4.86 out of 5 average rating, 207 reviews

A spacious living area features a large sectional sofa facing a media unit with a TV, accompanied by a coffee table. A dining table with four chairs sits nearby. Floor-to-ceiling windows provide bright natural light and a view of adjacent buildings.

Condo in Gold Coast

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

4.86 out of 5 average rating, 492 reviews

A cozy living area features exposed brick walls, a rustic wooden coffee table, and a large leather sofa. A flat-screen television is positioned in front of the seating, while natural light enters through the windows. A vintage fan rests nearby, and additional storage is provided by a bookshelf.

Condo in Humboldt Park

Humboldt Park Traveler's Lodge

Come stay at my gorgeous condo! Featuring exposed brick, a private entrance, stainless steel appliances, and a queen bed --> all on a quiet tree lined street! It's a perfect place to re-energize between big city adventures. Free street parking, and a 5 min walk to some of the best independently owned shops, restaurants, and bars in the city. Also, the massive and incredible Humboldt Park is also just a 5 min walk away! Please reach out for recommendations - I love giving them to people!

A modern kitchen features sleek gray cabinetry and stainless steel appliances, including a refrigerator and oven. A neutral area rug complements the wood flooring. Natural light is provided by large windows, and stylish wall decor adds a contemporary touch to the space.

4.98 out of 5 average rating, 225 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

4.96 out of 5 average rating, 141 reviews

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 Avondale

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.

4.98 out of 5 average rating, 191 reviews

A modern living area showcases a coffered ceiling and stylish furnishings. Plush sofas and accent chairs are arranged around a coffee table, with a large wall-mounted television and a decorative painting enhancing the aesthetic. Natural light enters through multiple windows, illuminating the space.

Condo in West Town

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Condo in Old Town Triangle

A cozy living area is presented with a daybed adorned with blue linens and colorful throw pillows. Light filters through two windows covered with sheer curtains. A wooden coffee table is positioned in front of a neutral-toned sofa, complemented by a bookshelf displaying various decorative items.

4.88 out of 5 average rating, 180 reviews

Lincoln Park Hideaway - 5 Min Walk to the Park!

800 sq ft 1 Bed 1 Bath Charming garden-level apartment right in the heart of Lincoln Park. Please note that you will need to walk down a short flight of stairs to access the unit. Close to all the best that Chicago has to offer! Walking distance to restaurants, convenience stores, and public transportation. Anything you could want for a nice trip to Chicago to visit friends and family, work relocation, or just explore our gorgeous city!

4.95 out of 5 average rating, 134 reviews

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

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.

5 out of 5 average rating, 149 reviews

A spacious living area features a comfortable sectional sofa, a wooden dining table with matching chairs, and a cozy reading nook with an armchair. Large windows allow natural light to fill the room, which includes a decorative fireplace and tasteful artwork on the walls.

Condo in Wicker Park

Stunning Wicker-Park Flat with Parking!

Enjoy a stylish experience at this centrally-located gem. Beautifully renovated 3 bedroom, 2 bath full floor flat. While quietly situated on the 3rd floor, you can walk out your front steps to all that Wicker Park and Division street has to offer. Coffee shops, bars, unlimited restaurants, green space, farmers market, gyms, grocery stores, and so much more. Easy and nearby public transit.

4.93 out of 5 average rating, 305 reviews

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

Picture Perfect 3Bed Steps from Train and FLW

Welcome to your beautiful 3 bedroom home-away-from-home! From the Insta-worthy forest room to the cozy fireplace reading nook to the modern ice crusher in the kitchen, we've put so much thought into this home that we're sure you won't ever want to leave. Welcoming and newly updated, this unit is close to restaurants, shopping, the best of Frank Lloyd Wright, and the train to the city.

A dining area showcases a long wooden table surrounded by six metal wire chairs. Natural light enters through two large windows, highlighting the warm wood finishes of the space. A sideboard with glass cabinets is visible against the wall, complemented by decorative art pieces.

4.98 out of 5 average rating, 418 reviews

Sunny Apartment Just 2 Blocks from Wrigley and Boystown

Located on a quiet, tree-lined street, the apartment sits on the second storey of a classic Chicago house in Lakeview—a vibrant lakefront community with arts and culture, green space, eateries, boutiques, nightlife, and transportation options. Street parking passes available upon request. Less than five minute walk to red line El (subway train) stop and several bus lines.

Popular amenities for Chicago condo rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.91 out of 5 average rating, 181 reviews

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 Humboldt Park

3 BR Sleek Minimalist Centrally Located Unit

Condo in Old Town Triangle

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.

4.95 out of 5 average rating, 118 reviews

NEW luxury Old Town 1-Bedroom condo

The living room features a comfortable sofa embellished with decorative pillows and a cozy throw. A gallery wall, adorned with framed photographs, adds visual interest. A wooden coffee table rests in front of the sofa, complemented by accent lighting on either side.

4.96 out of 5 average rating, 152 reviews

East Lakeview Designer Condo with 2 Bd, 2 Bath

4.88 out of 5 average rating, 149 reviews

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

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

4.92 out of 5 average rating, 378 reviews

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

Condo in Ukrainian Village

A cozy living area features a modern sectional sofa adorned with colorful cushions and a vibrant area rug. A wooden coffee table provides a natural accent, while bright artwork is displayed on the walls. Natural light filters through the window, and the main entrance is visible.

4.85 out of 5 average rating, 337 reviews

Welcoming 2BR in Chicago's Best Neighborhood!

Superhost

An open-concept living area features a spacious dining table surrounded by black chairs. A modern kitchen showcases stainless steel appliances and upper cabinets. Natural light fills the room through multiple windows, while a comfortable sofa is positioned nearby, welcoming relaxation in the thoughtfully designed space.

Condo in Lincoln Park

4.77 out of 5 average rating, 253 reviews

Modern Luxury In Old Town - Sleeps 4

4.97 out of 5 average rating, 159 reviews

A cozy living area features a modern fireplace surrounded by built-in shelving. A round dining table is positioned near large windows adorned with blue curtains, allowing natural light to fill the space. A decorative arrangement of branches adds a subtle touch to the room.

Condo in Near North Side

City Center Oasis: 3BR/2BA✔︎ Patio✔︎ Parking(2x) ✔︎

Pet-friendly condo rentals

4.84 out of 5 average rating, 390 reviews

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 North Side

Chic and Charming Vintage Condominium in Lincoln Park

4.95 out of 5 average rating, 109 reviews

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 Logan Square

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

4.93 out of 5 average rating, 151 reviews

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 Humboldt Park

Luxuriously bright 3-bedroom condo: The Treehouse

4.92 out of 5 average rating, 145 reviews

The modern kitchen features sleek white cabinetry and stainless steel appliances, including a refrigerator and oven. A central island provides extra counter space with two black stools positioned nearby. The open layout allows a view of the adjoining living area through a doorway.

Condo in North Side

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

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.

4.99 out of 5 average rating, 136 reviews

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

4.98 out of 5 average rating, 133 reviews

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 Edgewater Glen

Steps from the Lake, Lovely 3-Bedroom Condo

4.97 out of 5 average rating, 125 reviews

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 Lincoln Park

Large Remodeled Home in Lincoln Park, Sleeps 12!

4.93 out of 5 average rating, 109 reviews

A spacious living area features a mustard-colored sectional couch, accompanied by a small side table. Large windows allow natural light to fill the room, illuminating the modern decor. A flat-screen TV is mounted on the wall, and a cozy reading nook is visible through an open door.

Condo in Grant Park

Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS

Condo rentals with a pool

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.

4.96 out of 5 average rating, 109 reviews

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

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.

4.95 out of 5 average rating, 123 reviews

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

4.82 out of 5 average rating, 67 reviews

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

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

4.92 out of 5 average rating, 100 reviews

Just remodeled apartment close to airport and mall

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.

4.92 out of 5 average rating, 136 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

4.9 out of 5 average rating, 50 reviews

Pond View, Washer Dryer, Non Smoking Community

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.