Vacation rentals in West Side

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Top-rated vacation rentals in West Side

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A multi-level brick building features a modern entrance with a covered area and large glass doors. Window units are visible along the façade, surrounded by neat landscaping with low bushes and a paved driveway.

Apartment in Cicero

4.67 out of 5 average rating, 108 reviews

108 Mid-Century Rustic Studio

This is a BRAND NEWLY RENOVATED SPACE! It is a cozy apartment studio with ability to sleep 3 if needed. There are laundry facilities on site. A large flat screen smart tv with free wifi and a connected keyboard. Have access to a full kitchen with all the items needed for food prep and clean up. The CTA pink line, to and from Chicago, is a few blocks south for easy commuting. A Dollar General is across the street for groceries. There are many restaurants within a block and many other chains near.

Guest favorite

A modern kitchen area features white cabinetry and a sleek black refrigerator, complemented by stainless steel appliances. A round wooden dining table is set with four gray chairs. Exposed wooden beams enhance the open ceiling, illuminated by pendant lighting.

Apartment in Forest Park

4.86 out of 5 average rating, 117 reviews

City-Accessible Basement Retreat

Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

Guest favorite

The entrance features a dark metal door with mesh detailing, framed by stone pillars. A small set of stairs leads up to the door, while an overhead light illuminates the space. The number 3837 is prominently displayed above the entrance.

Apartment in Chicago

4.85 out of 5 average rating, 41 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

Apartment in Chicago

5 out of 5 average rating, 20 reviews

Bright and full of life!

Charming apartment steps away from iconic Route 66 (Ogden Avenue) and public transportation. Cozy retreat boasts a fully stocked kitchen, comfy beds, and a designated workspace with a printer - perfect for remote workers or travelers who need to stay productive. The apartment is filled with natural light and surrounded by lush greenery, including a beautiful veg garden in the summer and plenty of plants throughout. Sunny, bright space, and relaxing. Pet owners, furry friends are welcome here!

Superhost

The image captures a large, predominantly white building with elaborate architectural details. The structure is flanked by trees and a park area, showcasing expansive greenery in the foreground. A clear blue sky provides a bright backdrop to the urban setting.

Guest suite in Chicago

5 out of 5 average rating, 4 reviews

ENC-Chi Arts Suite Near United Center & Downtown

Enjoy a cozy stay in our garden level artist apartment below our private home as we embrace life as empty nesters. Centered in the East Garfield Park community. We’re just a 12-minute commute to downtown Chicago and 7 minutes to the West Loop, IL medical district, and United Center and three blocks from the popular Garfield Park Conservatory. Plus, conveniently located half a mile from essential amenities like grocer, fast-food, Chase bank, and Walgreens. Experience comfort and value with us!

Top guest favorite

A spacious living area is highlighted by sloped ceilings and wooden beams. A comfortable sectional sofa and a coffee table are nestled on a well-kept area rug. A television is positioned against the wall, while natural light filters in through two skylights.

Apartment in Chicago

4.99 out of 5 average rating, 137 reviews

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Guest favorite

A bright living room features oversized windows with soft drapes, allowing natural light to fill the space. A large, comfortable sectional sofa is complemented by a plush armchair, while a round coffee table rests in front of it. Decorative plants add a touch of greenery.

Apartment in Chicago

4.92 out of 5 average rating, 12 reviews

Stylish & Stunning 2BR/2BA Condo in the Heart of W

Experience modern luxury in this stunning 2BR/2BA condo in the heart of Wicker Park! This spacious 1,400 sq ft unit features a gourmet kitchen with quartz countertops, shaker cabinets, and a built-in wine cooler. The open-concept living space boasts high-end finishes, and oversized windows for abundant natural light. 2 on-site parking stalls and work stations. Just steps from trendy cafes, boutiques, and the Blue Line, this prime location offers the perfect mix of style and convenience!

Top guest favorite

A vibrant mural adorns the exterior of a multi-story building, featuring colorful depictions of skeletons and bright flowers. The design reflects cultural significance and artfulness, bringing life to the urban landscape. The building is situated at a traffic intersection, enhancing its visibility in the community.

Apartment in Chicago

5 out of 5 average rating, 11 reviews

2B Midcentury Artist Loft w King Bed

Welcome to Casa D'Mi Amá, this vibrant mid-century loft style apartment is centrally located in Little Village, one of the most vibrant Mexican-American communities and thriving shopping district in Chicago. Our community is known for its colorful murals and hundreds of Latinx-owned businesses and restaurants. We are just 4 mile away from downtown & Midway airport, three miles away from Pilsen & UIC, with public transportation right outside your door making it easy to plan your visit.

A spacious room features a comfortable bed with crisp white linens. A well-equipped kitchen area is located to one side, showcasing stainless steel appliances and wooden cabinetry. Natural light comes through a large window, highlighting the modern decor and textured wall art.

Apartment in Chicago

4.72 out of 5 average rating, 324 reviews

Sonder Market Hall | King Studio Apartment

Overlooking Union Park, Market Hall is the perfect blend of city and seclusion. You’ll have leafy green views, paved walking trails, and endless global cuisine options on Randolph Street. Each room includes a fully equipped kitchen, in-suite laundry, and a Roku for streaming. And take advantage of the free weights or machines in the fitness center. The West Loop is a trendy hot spot for foodies and entertainment seekers. Enjoy the best of the Windy City at Market Hall.

Top guest favorite

A modern living area features a green velvet couch and a round wooden coffee table atop a patterned area rug. A television is positioned on a media console, with natural light coming through multiple windows. Artwork adorns the walls, adding character to the space.

Apartment in Chicago

4.99 out of 5 average rating, 227 reviews

Modern Apt with style & comfort in Pilsen Chicago

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 cozy outdoor space features a small deck with wooden railings, alongside an inviting seating area furnished with a dark wicker couch and a low coffee table. Soft lighting is provided by hanging bulbs strung above the well-kept lawn, creating a relaxed atmosphere.

Apartment in Chicago

4.59 out of 5 average rating, 78 reviews

Cozy Basement Apartment - Great Location!

Check out our garden apartment on the border of Logan Square & Humboldt Park! It's right off the 606 Trail (which will lead you east to Bucktown & Wicker Park). Also, it is a short walk to either Humboldt Park or Logan Square. The layout - 1 spacious bedroom, full kitchen, private entrance, dining area and more. We're close to the Blue Line, so it's convenient to get here from O'Hare, & to the Loop!

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Popular amenities for West Side vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in West Side

Guest favorite

Apartment in Chicago

4.91 out of 5 average rating, 101 reviews

Family-Friendly 2BD/2BA Prime Location (+parking)

TiffanyRating, 5 stars2 weeks ago

Visited Chicago with family from LA and decided to stay in this beautiful home. We loved the spaces throughout the home especially the master bedroom’s bathroom. It was quite cold and windy when we were there and the heated flooring and hot tub in the bathroom really warmed us up. The neighborhood has great restaurants nearby that we visited and it was very peaceful. Nicole and Matt provided parking stickers and it was really convenience for us. We had a great time!

Top guest favorite

A spacious living area features a warm-toned seating arrangement with a brown leather sofa and a white accent chair. A large television is mounted on the wall opposite a decorative light fixture. Soft natural light floods in through large windows, complemented by light-colored curtains.

Home in Schaumburg

5 out of 5 average rating, 54 reviews

Great location-King beds-Kids playroom

SteveRating, 5 stars1 week ago

This Memorial Day some of my family stayed at Ninna's place and they absolutely loved the house! There were 4 spacious bedrooms, a beautiful children's room and the whole house was beautifully set up by Ninna. Would definitely book again!

Top guest favorite

A charming gray house with a well-maintained exterior is framed by a black fence. Steps lead up to a covered porch adorned with flower boxes, while a grassy area is visible beside the home, contributing to the inviting curb appeal.

Home in Chicago

5 out of 5 average rating, 16 reviews

Alluring Avondale Abode

MindyRating, 5 stars2 weeks ago

Beth was an amazing host! Super easy to work with! The place was beautiful, immaculate and comfortable. Would definitely stay there again!

Guest favorite

The living room features soft-toned walls, comfortable seating arrangements, and a large wall-mounted TV. A decorative stone fireplace adds a natural element to the space. A round wooden coffee table serves as a centerpiece on a light rug, enhancing the cozy atmosphere.

Apartment in Chicago

4.86 out of 5 average rating, 44 reviews

Elegant 4Bedroom with Free Parking in Albany Park

Melissa AnnRating, 5 stars1 month ago

We had a wonderful stay in Chicago! Beautiful house, very clean. Very nice neighborhood. We got confused about how to get in, it was our fault, we looked at the wrong number code. Loved having the garage for our van, not having to worry about parking was so nice and convenient! We would definitely come back!

Superhost

A modern dining area is highlighted by a wooden table surrounded by four chairs. The open-concept layout connects to a stylish kitchen featuring dark cabinetry and stainless steel appliances. Natural light fills the space, reflecting off the hard surface flooring and a cozy living room in the background.

Apartment in Chicago

4.66 out of 5 average rating, 29 reviews

City Gem: Stylish 3BR for Urban Explorers

ChelseyRating, 5 stars3 weeks ago

Great communication and very comfortable beds in all rooms

Superhost

The exterior entrance of the house is highlighted by a set of wooden stairs leading to a door with a sleek black finish. A decorative red tree provides a splash of color against the neutral siding, and a clear blue sky frames the scene.

Home in Chicago

4.83 out of 5 average rating, 102 reviews

California Cottage/4br prime location Logan Square

JimRating, 5 stars4 weeks ago

Great Stay in a Perfect Location We had a fantastic stay! The home was clean, well-equipped, and very comfortable. The location couldn’t be better—just 4 to 5 blocks (or less) from excellent restaurants and the train. Daniel and Carrie were wonderful hosts—responsive and quick to answer any questions. For dining, I highly recommend Lula Cafe, Same Day Cafe, and Mi Tocaya, which is literally just steps away. I wouldn’t hesitate to recommend this home for anyone visiting Chicago!

Guest favorite