Apartment holiday rentals in West Side

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.

4.99 out of 5 average rating, 108 reviews

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.

4.83 out of 5 average rating, 685 reviews

The main room features a day bed designed for versatile sleeping, accompanied by a cozy armchair. A round coffee table sits on a natural fiber rug, while a collection of decorative plates adorns the wall. Light enters through two windows covered with blackout curtains.

Flat in Oak Park

Sunny Jumbo Studio

Bright and sunny Oak Park jumbo garden studio, steps from cute downtown, train to Chicago, and amazing local tourist destinations- like the Hemingway Home and the Wright Studio. This welcoming studio was completely rehabbed and updated. We put a lot of care into designing a relaxing apartment with all the amenities. The main room features a king-sized bed, office nook, and fully stocked entertainment area, with games, books, and a TV. The spacious kitchen and luxurious bathroom are brand new!

An open kitchen space is highlighted, featuring a granite countertop and updated stainless steel appliances. Four high-backed bar stools are positioned around the breakfast bar. Light wood flooring complements the overall design, while natural light enters through nearby windows.

4.95 out of 5 average rating, 116 reviews

2-Bed 2-Bath Apt | close to UC w/ Free Parking

Welcome to the UC Commons, your Near West Side apartment just steps away from the United Center! Located minutes from Downtown Chicago, the West Loop, the Medical District, and public transportation, you will love your time here is Chicago. Bright & spacious interior, updated appliances, & thoughtful finishes is sure to have you feeling right at home. Whether you are coming for an event at the United Center or just want to explore our beautiful city, you will love your time at the UC Commons.

A modern kitchen and dining area are highlighted by sleek white cabinetry and stainless steel appliances. A spacious island with two stools provides seating, while a wooden dining table accommodates four. A decorative shelving unit displays various items, enhancing the clean aesthetic.

4.99 out of 5 average rating, 162 reviews

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.

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, 249 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.

4.91 out of 5 average rating, 191 reviews

Unmatched Urban Retreat Close to 18th Strip & Loop

This stylish Airbnb in the very popular Pilsen neighborhood is perfect for small and large travel groups. There are 2 bedrooms with queen size beds, and the couch folds out for an additional sleeping area. The 2 full bathrooms will have everything you need to get ready to hit the town. The tall ceilings make this space for larger than life, and the unique décor gives this Airbnb a great urban feel. The fully equipped kitchen and updated appliances are perfect for those quiet nights in.

A dining area features a wooden table with seating for four, positioned against a textured brick wall. Two windows allow natural light to fill the space, with sheer curtains gently framing them. A vibrant green plant and neon 'CHICAGO' sign add character to the room.

4.95 out of 5 average rating, 163 reviews

【Central】- Eclectic Fun 1BR APT in Wicker Park

Located in the heart of Wicker Park! Just a 5-min walk from the CTA blue line Damen station. This bright second floor 1-bedroom, 1-bath apartment allows you to access EVERYTHING Chicago has to offer all within short walking distance, with great nightlife. Just walk downstairs, you will find trendy restaurants, cocktail bars, cozy coffee shops and a variety of shops in this popular neighborhood. Want to explore downtown? Uber/Lyft or Hop on the CTA "L" train to go anywhere in the city.

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.

4.81 out of 5 average rating, 1,029 reviews

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.

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.

4.86 out of 5 average rating, 142 reviews

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

A bright and airy loft space is characterized by sloped ceilings and wooden paneling. A dark sofa is complemented by decorative pillows, while a small desk and chair are positioned by the window. Lush greenery adds a touch of nature to the cozy setting.

4.93 out of 5 average rating, 146 reviews

Comfortable and Cozy Apartment

Enjoy this simple and cozy apartment! Located just a few blocks from stores like Walgreens, Aldi, Target, Laundromat and various restaurants. Its conveniently located just a 10 minute walk from the orange line cta train station. Disfrutá de la sencillez de este alojamiento tranquilo y céntrico. Ubicada a dos minutos de tiendas como target, Walgreens, Aldi, Lavandería y restaurantes . Estamos a 10 minutos del aeropuerto midway y 15 minutos del centro de Chicago.

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.

4.95 out of 5 average rating, 127 reviews

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.