Apartment holiday rentals in West Side

4.99 out of 5 average rating, 112 reviews

A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.

Flat in West Rogers Park

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Flat in Ukrainian Village

A spacious living area showcases warm wooden floors and a dark brown accent wall. A blue sofa is complemented by colorful cushions, while a wooden coffee table sits in front. Artwork and decorative pieces adorn the walls, and natural light filters through large windows.

4.92 out of 5 average rating, 271 reviews

iKlektik House Chicago/BlueJay

A Space perfect for Two Adults with warm heated floors and amazing craftsmanship + artwork. Custom made built-in king size bed. Large custom kitchen, butcher block and claw foot tub in bathroom. Not suitable for infants/children. WE DO NOT RENT ON "CL" DO NOT WIRE $ IT'S A SCAM CLOSE TO THE UNITED CENTER New restaurants and neighborhood favorites, along with cocktail bars and music venues. Metra, Cta {buses and trains} close by. Metra: Western & Hubbard Free Street Parking Right Out Front!

4.87 out of 5 average rating, 317 reviews

The kitchen area features white cabinetry and stainless steel appliances, including a microwave and refrigerator. A wooden table with high stools provides dining space, while light pours in from a window. A decorative wall piece and potted plant add a touch of interest.

Flat in West Side

Cozy Spacious Condo Sleeps 6

Our welcoming second-floor apartment offers a relaxing updated space to call home during your stay in Chicago. We designed the space to be a home away from home. The apartment's 2 bedrooms and spacious daybed, that converts to a king bed, will ensure you are well-rested and recharged so that you can fully enjoy our wonderful city. Whether you are in town for work or for pleasure our condo will make your stay a great one! We deliver as SUPERHOSTS. We ask that you respect all house rules! Thx

Flat in Ukrainian Village

A modern living room features a gray sofa adorned with plush pillows, accompanied by stylish accent chairs. A coffee table sits centrally on a textured rug, while a large window bathes the space in natural light, showcasing decorative plants and contemporary wall art.

4.92 out of 5 average rating, 441 reviews

Bright, Modern Apartment in a Vintage Greystone

Enjoy morning coffee by the sunny bay window in this vintage apartment with classic modern style. The apartment features vintage charm with modern amenities, queen memory foam bed in bedroom and queen sofa bed in living room. Parking is available in the back lot for an additional $25 per night. For reservations over three weeks, we require a cleaning every 2 weeks at a cost of $60 per cleaning. Apartment is located on the 3rd floor of a three story building and you will need to climb stairs.

Flat in Ukrainian Village

A welcoming living space features a blend of modern and natural elements. A green accent wall provides a backdrop to a cozy seating area with black chairs and a sofa. Decorative plants are placed throughout, enhancing the bright and open atmosphere.

4.98 out of 5 average rating, 253 reviews

Bright Cozy Modern-Chic Condo in Trendy West Town

Kick back & relax in your home away from home in our luxurious, spacious and peaceful abode in the heart of the West Town & Noble Square neighborhoods, close to downtown. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located near the popular Grand Avenue, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

4.95 out of 5 average rating, 111 reviews

An open kitchen and dining area feature a modern design with sleek cabinetry and a large island. A generous dining table, surrounded by black chairs, offers seating for multiple guests. Natural light floods the space through large windows, with minimal decor enhancing the contemporary aesthetic.

Flat in Downtown Chicago

Luxury Loft Collection 03 - Terrace - River North

BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious building in bustling River North-the city's center of main nightlife and restaurants. This ultra high-end apartment features a private elevator, private terrace, free secured parking, 24 hour doorman, 3 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

4.81 out of 5 average rating, 1041 reviews

A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.

Flat in Downtown Chicago

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

5.0 out of 5 average rating, 111 reviews

A spacious dining area is highlighted by a contemporary chandelier above a wooden table set for four. Transparent chairs provide a modern touch, complemented by decorative accents on the sideboard and the elegant wooden columns framing the open space, enhancing the flow between rooms.

Flat in Wicker Park

The Bell House: Apartment #1

Charming 2BR Wicker Park apartment blends modern luxury with historical charm. Fully renovated; new appliances, private deck, full kitchen with cookware, & dedicated workspace. Steps from bars, restaurants, and Blue Line for city/airport access. Ideal for both leisure and business travelers seeking a comfortable, convenient Chicago stay. We offer a unique blend of comfort and location in a vibrant neighborhood. Perfect for exploring on foot, but ample street parking as well!

4.86 out of 5 average rating, 146 reviews

A stylish living area is featured, showcasing a green sofa arranged with a round glass coffee table atop a black and white patterned rug. A wall-mounted TV is present, alongside a dining table with two chairs. Large windows allow natural light to fill the space.

Flat in West Side

Renovated LittleVillage Retreat

Welcome to our newly renovated retreat in Little Village, Chicago! This stylish unit blends modern amenities with classic charm. Features include a cozy living area with a smart TV, a fully equipped kitchen with stainless steel appliances, a comfortable bedroom with a work desk, and a pristine bathroom with contemporary design. Enjoy in-unit laundry and a secure entry. Convenient street parking and close to local attractions and dining. Perfect for early birds and explorers

4.78 out of 5 average rating, 578 reviews

A modern kitchen features stainless steel appliances including a gas stove, microwave, and refrigerator. White cabinetry complements the light countertops. Natural light enters through a window above the sink. A small area rug adds warmth to the hardwood floor, with a dining table visible in the background.

Flat in Logan Square

Sun filled tranquil 2 br great part of Logan Sq.

Clean, comfortable and peaceful 2 bedroom apartment close to great food, parks, 606 trail, vibrant night life and shopping. Great area of Logan Square that is good for couples, solo adventurers, business travelers and anyone who seeks a great apartment in a great neighborhood with easy access to many of the best places in the city. Youtube live TV. Nice back patio with table and chairs. Free street parking, no meters, no time restrictions or permits needed.

4.95 out of 5 average rating, 132 reviews

A modern kitchen is showcased, featuring sleek cabinetry in dark tones and stainless steel appliances. An island with a light countertop provides ample space for meal preparation. Natural light enters through large windows, brightening the inviting atmosphere of the open layout.

Flat in West Side

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.