Apartment holiday rentals in West Side

A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.

5 out of 5 average rating, 315 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

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, 257 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!

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, 242 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.

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 out of 5 average rating, 105 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!

A spacious bedroom features a king bed with a memory foam mattress centered against a decorative wall panel. Two potted plants add greenery to the room, with modern pendant lights providing illumination. Large windows allow natural light to fill the space, complemented by a comfortable chair and a mirrored wardrobe.

4.91 out of 5 average rating, 223 reviews

Lovely 1-bedroom serviced apartment near Museums!

Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

An open-concept living area is presented with exposed brick walls, a dark blue couch, and a round coffee table. A light-colored accent chair and a small side table provide additional seating. A potted plant adds a touch of greenery beside the couch, enhancing the modern aesthetic.

4.84 out of 5 average rating, 153 reviews

The Chicago Cozy Brick Retreat

This unit offers a charming blend of modern amenities and historic charm. This thoughtfully designed unit features an open-concept living space with exposed brick walls and stylish furnishings. The fully equipped kitchen boasts new appliances, perfect for culinary adventures. The comfortable bedroom, with a cozy bed and ample storage, ensures a restful stay. The sleek bathroom includes contemporary fixtures and a walk-in shower. Street parking is easily available.

A modern living area features a comfortable sectional couch, complemented by decorative pillows. Natural light enters through large windows, illuminating the space. A flat-screen TV is positioned on a wooden media console, and a dining area with a bar counter is visible in the background.

4.91 out of 5 average rating, 106 reviews

Blue Brick Apartment in Bridgeport - Park for Free

• Free street parking • Trains to Downtown!! • Fully stocked kitchen • Walk to dining & bars! • Free parking pad in rear • Noise monitoring equipment • Walk score 93! Bike Score 92! • 600 sq ft apartment | 1st floor | Patio • Safe, working class neighborhood! • Commute to Downtown: 15min (drive) • 28min (transit/train) | 22min(bike) • Building video surveillance alarm system • Washer | Dryer | Dishwasher are included • Rideshare (Uber/Lyft) | Bikeshares(Divvy)

4.93 out of 5 average rating, 238 reviews

Apartment in Maywood

Cozy guest studio, great for couples!

This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

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.

4.77 out of 5 average rating, 568 reviews

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.

A modern kitchen features sleek black cabinetry and appliances, complemented by a contrasting white countertop. Stylish stools are arranged around a small kitchen island. The wall is adorned with a framed painting, while decorative items are displayed on open shelves above the countertop.

4.88 out of 5 average rating, 324 reviews

Spectacular Pilsen Studio for 2!

This chic studio in the heart of Pilsen is the perfect space to kick back and relax during your visit to the Windy City! The vibrant neighborhood always has something to offer to any type of traveler, and it's a quick trip to see most of the iconic Chicago sights. Easily walk to historic Thalia Hall, or drive to the Loop in just 5 minutes! You'll love the thoughtful touches and modern decor in the apartment, as well as the bright and welcoming main space.

4.99 out of 5 average rating, 280 reviews

Quaint Comfort Studio Near Downtown/Queen Bed

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

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.