Apartment vacation rentals in South Side

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Top-rated apartment rentals in South 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
4.99 out of 5 average rating, 108 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 vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.
Apartment in Chicago
4.92 out of 5 average rating, 166 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TV, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles), Navy Pier, Obama Library, Millennium Park, Beach (1 mile), Museum, & Sports arenas.

Superhost
Apartment in Chicago
5 out of 5 average rating, 4 reviews

Simply Sleek & Uneek: Mins To/Fr D'Town Chicago

Simple Sleek Minimalist 1-BDR Condo at the Crossroads of Bronzeville, Kenwood & Hyde Park: Situated at the intersection of historic Bronzeville, elegant Kenwood, & culturally rich Hyde Park, this 1-BDR, condo offers a peaceful retreat just minutes from downtown Chicago & the Lake. Featuring a large living room, fully equipped kitchen, & private bathroom; designed with your comfort & convenience in mind. It's an ideal home base whether you’re visiting for work/business, school, or a getaway.

Guest favorite
Apartment in Chicago
4.86 out of 5 average rating, 7 reviews

Serene retreat near Obama center & public trans

Escape to our unique historic bungalow in South Shore. Perfect for architecture lovers, this serene retreat is designed with peace and comfort in mind. Features a dedicated office, and three outdoor spaces, including a private yard with a fire pit. Just minutes from Lake Michigan, the childhood home of Michelle Obama and the Obama Presidential Center is minutes away. The Museum of Science & Industry, 3 beaches & golfing are nearby. Your private, and peaceful getaway awaits.

Guest favorite
A bright and airy loft space is characterized by sloped ceilings and wooden paneling. A dark sofa is complemented by decorative pillows, while a small desk and chair are positioned by the window. Lush greenery adds a touch of nature to the cozy setting.
Apartment in Chicago
4.94 out of 5 average rating, 135 reviews

Comfortable and Cozy Apartment

Enjoy this simple and cozy apartment! Located just a few blocks from stores like Walgreens, Aldi, Target, Laundromat and various restaurants. Its conveniently located just a 10 minute walk from the orange line cta train station. Disfrutá de la sencillez de este alojamiento tranquilo y céntrico. Ubicada a dos minutos de tiendas como target, Walgreens, Aldi, Lavandería y restaurantes . Estamos a 10 minutos del aeropuerto midway y 15 minutos del centro de Chicago.

Top guest favorite
A brightly illuminated living area features a light-colored sofa adorned with decorative cushions. A modern coffee table sits centrally, while colorful artwork enhances the walls. The space opens toward a dining area, with a glimpse of the kitchen visible in the background.
Apartment in Chicago
5 out of 5 average rating, 34 reviews

Blake’s Place

Welcome to our charming Air BnB! Nestled in a prime location, this cozy and stylish space is perfect for your getaway. With its tastefully designed interiors, and comfortable furnishings, you'll feel right at home. Our place features plush double queen size bunk beds for a restful sleep, while the fully equipped kitchen allows you to prepare delicious meals. Relax in the inviting living area or step out and enjoy a nice walk along Lake Michigan just 10 mins away.

Guest favorite
A cozy living room area features a dark leather sofa facing a mounted television on a wooden media console. A round shelf displays books and plants, while a small desk and chair are positioned beside a bright window.
Apartment in Chicago
4.93 out of 5 average rating, 231 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 | 2nd 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)

Superhost
The kitchen features modern white cabinetry, stainless steel appliances, and a gas stove. Counter space is clear, with utensils and cooking tools organized nearby. A bright turquoise kettle adds a pop of color, while light reflects off the sleek surfaces, enhancing the kitchen's functionality.
Apartment in Chicago
4.84 out of 5 average rating, 114 reviews

2 15 min to Downtown Next to UniversityTrain Park

☞ 1 Smart TV ☞ Fully equipped + stocked kitchen ☞ Self check-in ☞ Luggage storage available ☞ Onsite washer + dryer in basement ☞ Air conditioning 》35 mins to airport 》15 mins to Downtown Chicago 》 Minutes walk to train station 》 Walking distance to University of Chicago 》 Across street from parks Minutes walk to train station 》2 bedroom, 1 bathroom 》Sleep 6 If you need additional bedrooms please reach out we other units in the same building

Top 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
4.95 out of 5 average rating, 118 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.

Superhost
Apartment in Chicago
4.86 out of 5 average rating, 115 reviews

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.

Superhost
Apartment in Chicago
4.5 out of 5 average rating, 20 reviews

Relaxed Hyde Park Studio Getaway Near Downtown

Stay in the heart of Hyde Park in this comfy studio just steps from the University of Chicago, 53rd Street shops, cafés, and the lakefront. The space has a queen bed, full kitchen, Roku TV, and in-unit washer/dryer, making it easy to settle in. Bright and thoughtfully decorated, it’s a perfect spot to relax after exploring the neighborhood. Easy access to Metra and buses gets you downtown in minutes.

Superhost
Apartment in Chicago
4.8 out of 5 average rating, 15 reviews

Stunning 1BR Haven with Lake & Skyline Views

Enjoy stunning views of the Chicago skyline and Lake Michigan from this beautifully fully furnished 1-bedroom apartment. Thoughtfully designed for comfort and convenience, it’s a move-in-ready space that lets you relax above the city in style.

Popular amenities for South Side apartment rentals

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