Condo holiday rentals in Chicago

4.88 out of 5 average rating, 445 reviews

A modern living area features two stylish seating options, one bright green sofa and a deep blue accent chair with matching ottoman. Natural light filters through large windows adorned with horizontal blinds, highlighting the light wood flooring and contemporary decor.

Condo in Little Village

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen

Brand New Private Modern 2 bd 2bth apt for your stay in Chicago. We are located 2 blocks form the CTA line in the heart of Pilsen, a neighborhood Time Out labeled the 10th coolest in the world. Newly renovated, hardwood tiled floors throughout, chefs kitchen, toiletries, brand new furnishings including 2 queen beds, 1 twin sleeper, fresh linen, smart TV (HBO, Netflix, Hulu) wifi, tons of books,coloring books,board games & puzzles! We truly want you to feel like this is your home away from home.

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!

4.98 out of 5 average rating, 225 reviews

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.

Condo in Lake View

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

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

4.88 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!

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.

5 out of 5 average rating, 118 reviews

Condo in Logan Square

Inspired, luxe living in Logan Square on BLVD #1

Welcome to our Palmer Square House! In the heart of hip Logan Square. Enjoy a rare opportunity to experience Boulevard living. "Live like a local" in one of Chicago's most visited & vibrant neighborhoods. 1915 historic 2-flat has been renovated with luxurious amenities. Lots of windows provide natural light. Chef's kitchen is beautiful & functional. Option to rent PH at same time if available. Primary bathroom has serious spa vibes. NO CLEANING FEES! Very fast WiFi. 65" Smart TV QLED.

4.94 out of 5 average rating, 127 reviews

The living area features a spacious gray sectional sofa complemented by a textured area rug. A sleek coffee table is adorned with decorative items, while a stylish arc floor lamp provides ambient lighting. In the background, a dining space with a round table and four chairs is visible.

Condo in Gold Coast

GLORIOUS GOLD COAST GETAWAY

Welcome! Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier. We look forward to hosting you!

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.

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!

4.9 out of 5 average rating, 175 reviews

A modern kitchen with white cabinetry features stainless steel appliances, including a refrigerator and microwave. An island with seating for three is complemented by decorative vases of flowers. Natural light fills the space through large east-facing windows.

Condo in Gold Coast

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

Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

4.98 out of 5 average rating, 417 reviews

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.

Condo in Lake View

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.

4.97 out of 5 average rating, 459 reviews

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 Lincoln Square

Lincoln Square Gem!

Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. My partner and I live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!

4.97 out of 5 average rating, 867 reviews

A spacious living room features three large windows allowing natural light to fill the space. Comfortable seating includes a leather couch and an armchair. A television is mounted on the wall, and a decorative area rug lies beneath a wooden table set for dining.

Condo in Noble Square

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Popular amenities for Chicago condo rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.79 out of 5 average rating, 244 reviews

The image showcases a residential building with multiple stories and a set of wooden stairs leading to the entrance. A fenced outdoor area includes a picnic table and a grill, offering a space for gatherings. A parking structure is located in the background.

Condo in Wrigleyville

Wrigley Residence in Iconic Wrigley Rooftop

4.9 out of 5 average rating, 102 reviews

The living room features a spacious, light-colored sectional sofa adorned with orange and black cushions. A coffee table sits in front, accompanied by a cozy pouf on a patterned rug. A mounted TV is visible, along with large windows allowing natural light to brighten the room.

Condo in West Town

Welcome to the Chi! Close to Downtown

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

4.93 out of 5 average rating, 280 reviews

A comfortable living area features a dark sofa with colorful accent pillows and a glass coffee table. Natural light streams through large windows, which are dressed with sheer white curtains. A modern floor lamp and a single chair add functional seating options.

Condo in Humboldt Park

Modern/Spacious 2BR/2BA West Town

4.92 out of 5 average rating, 377 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

4.85 out of 5 average rating, 110 reviews

A spacious bed with soft beige linens is centered in the room, accompanied by two pillows. A light fixture stands on each side of the bed, while an abstract painting in yellow and dark tones hangs above, adding a pop of color to the neutral palette.

Condo in Lake View

Private 1 bedroom apartment

4.92 out of 5 average rating, 189 reviews

Condo in Uptown

Vibrant, Sunny & Spacious 2 bd 1 ba Uptown Condo

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.

4.78 out of 5 average rating, 685 reviews

Spacious Evanston Unit - Walk to Northwestern U

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

Condo in Ukrainian Village

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.

4.98 out of 5 average rating, 106 reviews

Spacious 3BR/3BA Condo in Trendy Ukrainian Village

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

4.94 out of 5 average rating, 151 reviews

A spacious modern family room features a large sectional sofa adorned with decorative pillows. A 76” smart TV is mounted on the wall, displaying a beach scene. Natural light enters through multiple windows, illuminating the open layout that flows into a dining area with sleek furniture.

Condo in East Pilsen

The Urban Oasis | Outdoor Lounge • Sleeps 10+

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

4.91 out of 5 average rating, 106 reviews

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

Spacious 5-BR Apt next to transit Free Parking

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

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.