Vacation rentals in West Side

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Top-rated vacation rentals in West Side

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Top guest favorite

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.

Apartment in Chicago

5 out of 5 average rating, 61 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.

Guest favorite

A cozy living area showcases orange sofas arranged around a dark wooden coffee table. Large windows with blinds offer natural light, while a vibrant mural of a city skyline adds visual interest. A ceiling fan provides circulation, enhancing comfort in the space.

Apartment in Chicago

4.81 out of 5 average rating, 59 reviews

Dwntown Mins Away/Relax & Stay! Bus/Train Friendly

Take it easy in this peaceful and cozy sleeper, central to everything Chicago has to offer and only minutes from downtown. Take advantage of all of the amenities while your here and enjoy the city night life with all of the great entertainment and restaurants Chicago has to offer. Newley rehabbed with high end appliances and fixtures that you, your significant other or family can enjoy. This relaxing vibe is one that will make it feel like a home away from home with all that it has to offer.

Guest favorite

A cozy living area features a gray sofa adorned with patterned cushions, complemented by a light-colored coffee table. Wooden flooring adds warmth, and large windows are draped with sheer curtains, allowing natural light to brighten the space. A small workspace is visible in the corner.

Apartment in Cicero

4.96 out of 5 average rating, 342 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

Guest favorite

A spacious living area is highlighted by a black sofa facing a light-colored coffee table. A vibrant area rug adds color underfoot. The walls are adorned with colorful vinyl records and framed artwork, while original woodwork details frame the open layout leading to the dining area.

Apartment in Oak Park

4.86 out of 5 average rating, 689 reviews

Rockin' 2Bed steps to shops/food/train

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

Top guest favorite

A fenced backyard features a circular arrangement of wooden lounge chairs centered around a propane fire pit, creating a cozy gathering space. Twinkling string lights hang above, illuminating a bistro table with two blue chairs. Lush green grass surrounds the stone patio area.

Home in Berwyn

4.98 out of 5 average rating, 169 reviews

Retro Modern Bungalow | fire pit | free parking

Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Guest favorite

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

4.9 out of 5 average rating, 349 reviews

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.

Guest favorite

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.

Apartment in Chicago

4.83 out of 5 average rating, 827 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.

Guest favorite

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.

Apartment in Chicago

4.85 out of 5 average rating, 308 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.

Guest favorite

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.

Apartment in Chicago

4.93 out of 5 average rating, 76 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.

Guest favorite

Private room in Des Plaines

4.88 out of 5 average rating, 367 reviews

R1 Delightful room in quiet neighborhood

A cozy room located in peaceful neighborhood, a perfect place to stop after traveling from O'Hare airport! We have a beautiful wild river, lake, and forest right in the backyard and surrounding our area, with wild life creating a cozy atmosphere, amazing to take walks. We are a 10 minute ride from the O'Hare International Airport, a 5 minute ride from a Metra Station, and surrounded by all kinds of parks and interesting restaurants.

Top guest favorite

Two hanging chairs are positioned on a covered patio, surrounded by lush greenery and decorative plants. A small garden structure adds privacy, while the floor features a vibrant red surface. Ambient light filters through the overhead structure, creating a relaxed outdoor space.

Home in Chicago

5 out of 5 average rating, 20 reviews

Chicago Row House Garden Apartmt

This stylish urban garden apartment is a comfortable stay just a few blocks from the United Center and 1 mile from the very popular West Loop and Fulton Market areas! Street parking is readily available and free! We are a 3 mile straight shot down to Millennium Park in the Loop. Take the “L”, bike or walk there and hit Greek Town, the Lyric Opera, the Sears (Willis) Tower, the Art Institute and the Bean (Cloud Gate) along the way!

Guest favorite

The modern kitchen features white cabinets and a polished countertop. Stainless steel appliances, including a gas stove and dishwasher, are visible. A window allows natural light to enter, illuminating the functional space.

Guesthouse in Chicago

4.95 out of 5 average rating, 40 reviews

Cozy Coach House Retreat Near Downtown!

Fully remodeled coach house centrally located in Chicago! Most tourist attractions are within a 15 drive or less! Public transportation is within a 3 min walk. You'll also have access to the shared rooftop deck (Furniture available May 5th-Sept 30th). This cozy unit offers 1 Queen bed + 1 bath, 1 Queen size air mattress provided, fully stocked kitchen and spacious living room space! Free Street Parking in the Area