Apartment vacation 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, 295 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.

4.83 out of 5 average rating, 643 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.

Apartment 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!

The living room features a stone accent wall with a mounted flat-screen TV centered above a fireplace. Dark blue sofas are arranged around a light-colored ottoman, while a patterned area rug extends across the dark wood floor. Natural light enters through the nearby window.

4.99 out of 5 average rating, 267 reviews

Spacious 2BR on Quiet St - Free Park/Late Checkout

2 bedroom, 1 bathroom apartment, located just off Taylor Street in the heart Little Italy! Safe and lively neighborhood with many diverse restaurants, cafes, bakeries, parks, etc. all just a short walk from the apartment! Nearby West Loop also packed with trendy shops and amazing dining spots. Flat screen TV in every room, In-unit laundry, patio space, coffee/tea provided. 1pm check out 👍 Easily accessible to United Center, Soldier Field and downtown. Located on Chicago Marathon route.

The living area is furnished with a gray sofa adorned with patterned cushions, positioned next to a natural wood coffee table. A potted plant and a decorative mirror enhance the space. Two windows allow natural light to brighten the room.

4.94 out of 5 average rating, 173 reviews

Cute, Clean, Cozy Apartment in Pilsen

Updated, clean and private apartment in Chicago’s unique Pilsen neighborhood. Located on a quiet, tree-lined street with private entrance, it's the perfect spot to rest after a day of exploring this great neighborhood and city. The apartment has a full kitchen with everything needed to make your morning coffee or prepare a meal. Conveniently located to McCormick Place and many of the city's attractions, including West Loop, downtown, United Center, Grant / Union / Douglass Park and more!

A living area features a dark leather sofa with red accent pillows, paired with two leather chairs. A wooden coffee table sits centrally, surrounded by warm-toned lighting. The space opens to a kitchenette with a retro red refrigerator and tall bar seating, creating an inviting atmosphere.

4.86 out of 5 average rating, 249 reviews

Cozy & Comfy 1bd In Historic Portage Park Bungalow

Make yourself at home in my comfortable Portage Park one bedroom garden apartment. This spacious condo is bright and airy with warm furnishings, a kitchenette with an island, private bedroom with a full bed and a modern bathroom with a glass walk-in shower. Portage Park is Chicago’s largest Polish neighborhood and is home to vintage charm, heaps of history and classic Chicago-style bungalows. The National Veterans Art Museum is a poignant must-see while you’re here with its combat-era art.

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.

4.99 out of 5 average rating, 202 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.

4.9 out of 5 average rating, 365 reviews

The living room features a spacious teal sofa paired with a simple black coffee table in front. A window with sheer curtains allows natural light to fill the area, complemented by a floor lamp and potted plants. Hardwood floors add warmth to the room.

Apartment in Berwyn

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

The living room is well-lit by sunlight streaming through three large windows, accentuating a comfortable brown sofa and a stylish armchair. A wooden coffee table and a small dining table with two chairs offer ample seating. Unique artwork and decorative items add character to the space.

4.97 out of 5 average rating, 574 reviews

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

4.91 out of 5 average rating, 452 reviews

A bright kitchen area features a round table with a red and white checkered tablecloth and four white chairs. A small sink and a gas stove are present, along with a refrigerator. Natural light filters through a window adorned with a red gingham curtain.

Apartment in Berwyn

Private apartment with retro vibe

December discount dates! Cozy 1 BR apartment with retro touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus brand new twin sofa bed, + 1 more twin available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left

A vintage-style sign featuring bold red and white lettering, stating 'Bohemian Lodge no 17' against a dark brown background. Decorative elements include images of beer glasses and whimsical knot designs, creating a nostalgic atmosphere.

4.85 out of 5 average rating, 317 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond to our house rules.

A cozy living area features two dark leather sofas, a marble-topped coffee table, and a flat-screen television. Natural light enters through a window with blinds, while a warm brick wall adds character. A decorative console table is positioned along the side of the room.

4.91 out of 5 average rating, 274 reviews

Newly Rehabbed! 2br with Vintage Charm

Our 2 bed garden apartment in Ravenswood will be the ideal home base for your stay! Located in one of Chicago's vibrant Northside neighborhoods, you’ll experience local charm outside your door. The home has space for 5 and a newly renovated kitchen, though you may not have time to cook with many family-owned restaurants within walking distance! The Montrose Brown Line is only 3 blocks away, taking you downtown in 30 minutes and Lakeview/Lincoln Park in even less.

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.