Apartment holiday rentals in West Side

4.99 out of 5 average rating, 111 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.

Superhost

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

4.87 out of 5 average rating, 317 reviews

A spacious living area features large windows allowing ample natural light. Contemporary furniture is arranged for comfort, including a leather sectional, accent chairs, and a round ottoman. The open layout leads to a modern kitchen, creating an inviting and functional space for gatherings.

4.9 out of 5 average rating, 150 reviews

Luxury Designer Penthouse Loft | Sleeps 20

Designer Penthouse in the heart of Wicker Park! Sleeps up to 20 people! Enjoy your own private loft in Chicago's hip and trendy Wicker Park-one of the city's centers nightlife, restaurants and cultural scene. This 4,500 square foot penthouse sits on an entire floor features 18 foot open vaulted ceilings, authentic loft feel, 4 bedrooms/3 bathrooms, and is perfect for families, professionals visiting the city on work trips, and everything in between. The cityscape views are truly unbeatable!

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.

Superhost

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.

4.81 out of 5 average rating, 1040 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.

5.0 out of 5 average rating, 110 reviews

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!

4.95 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.

Superhost

Flat in West Loop

LIVN West Loop Chicago Queen Studio Apartment

Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.

4.83 out of 5 average rating, 184 reviews

4.96 out of 5 average rating, 156 reviews

A modern living room features a light gray sofa paired with dark accent pillows. Natural light fills the space through large windows, complemented by dark curtains. A stylish armchair and a side table sit next to the sofa, while a flat-screen TV is mounted on the wall.

Flat in West Side

Private Balcony, Parking, 5 Min to UC

- Relax in a spacious, modern condo with a private balcony and stunning skyline views - Enjoy the comfort of a chef’s kitchen and high-end appliances for home-cooked meals - Secure indoor parking and free street parking, plus an EV charger for your convenience - Perfect for families, groups, and business travelers with ample space to unwind - Book your stay today and experience the best of Chicago in comfort and style

4.92 out of 5 average rating, 186 reviews

A modern rooftop deck is presented, featuring contemporary seating with vibrant orange cushions arranged around a firepit. Panoramic views of the Chicago skyline are visible, showcasing a mix of architectural styles under a clear blue sky.

Flat in Downtown Chicago

Modern 3BR with Private Rooftop & Free Parking

A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.

The modern kitchen features navy blue cabinetry and a central island with seating for three. Stainless steel appliances include a refrigerator, stove, and dishwasher. Pendant lighting hangs above the island, and a window provides natural light, complementing decorative wall art.

4.92 out of 5 average rating, 204 reviews

Stylish 2BR stunner w/ unbeatable location

Discover the perfect urban retreat in a newly renovated flat with all the modern amenities. Nestled at the border of Ukrainian Village and Wicker Park, this classic Chicago 2-flat offers modern amenities in a historic setting, tucked away in a peaceful corner just steps away from the vibrant city life of Division and Damen with its countless restaurants, watering holes, and one-of-a-kind shops.