Apartment vacation rentals in South Side

Find and book unique apartments on Airbnb

Top-rated apartment rentals in South Side

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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, 131 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 TVs, 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 to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

Superhost

A well-maintained outdoor space is presented, featuring a manicured lawn surrounded by tall greenery and colorful flower beds. A two-story structure with a wooden deck is visible, along with a walkway leading through the garden, creating an inviting environment for relaxation.

Apartment in Chicago

4.87 out of 5 average rating, 255 reviews

Historic Coach House Cottage

Historic Coach House Cottage- Nestled in Bronzeville community and nearby Historic Hyde Park neighborhood that is safe and family oriented. Ideal for relaxation, peace & quiet. Cozy and quaint with flower and vegetation garden landscape. Centrally located 1.5 miles from lake front, nearby shopping, movie theater, and restaurants in Hyde Park. Seconds from park, walking track and playground. 15 Minutes from downtown and Magnificent Mile. Local transportation and bike rental within blocks.

Guest favorite

A compact sitting area features a beige loveseat adorned with decorative pillows. It is positioned on a patterned area rug, adding contrast to the ceramic tiled floor. Natural light filters through a window with horizontal blinds, enhancing the cozy ambiance of the space.

Apartment in Chicago

4.8 out of 5 average rating, 259 reviews

Cozy Studio Apt. Home-5 Min. to U of C

A private guest suite 5 min. from UChicago campus. Full access via private entrance to cozy studio created in bsmt of our home. An open floor plan with louvered wooden doors close off bedroom w/dbl bed. A full kitchen, ceramic tile bath w/tub, hand-held shower head+vanity mirror. Studio guest: "Your place really stands out from all the landlord-managed airbnb stuff in Hyde Park!" Five min. to campus, fitness ctr, & CourtTheatre; convenient, cozy & private. Registration #R24000123950

Guest favorite

A spacious living room is displayed, featuring a large sectional sofa adorned with decorative pillows. A glass coffee table rests on a patterned rug, while creative wall art and a wooden sculpture enhance the atmosphere. Soft lighting from a ceiling fan provides a warm ambiance.

Apartment in Chicago

5 out of 5 average rating, 38 reviews

Private Duplex w/ Theater + Games | Near UChicago

Enjoy endless entertainment with family and friends in our spacious 2-level home, equipped with central air and heating! The lower level is your fun zone—featuring a 120" projector for movies, a retro arcade game, ping pong, board games, a bedroom and bath, and a reclining sectional for movie nights! Upstairs, you'll find 2 bedrooms, a full bath, a patio with new furniture, and a fully stocked kitchen with appliances and complimentary coffee. Everything needed for a fun, comfortable stay.

Superhost

Apartment in Chicago

4.9 out of 5 average rating, 128 reviews

Unmatched Urban Retreat Close to 18th Strip & Loop

This stylish Airbnb in the very popular Pilsen neighborhood is perfect for small and large travel groups. There are 2 bedrooms with queen size beds, and the couch folds out for an additional sleeping area. The 2 full bathrooms will have everything you need to get ready to hit the town. The tall ceilings make this space for larger than life, and the unique décor gives this Airbnb a great urban feel. The fully equipped kitchen and updated appliances are perfect for those quiet nights in.

Superhost

A modern living area features a plush area rug over hardwood flooring. An arrangement of seating is complemented by a sleek ceiling fan and a large television mounted above a fireplace. Bright windows provide natural light, with greenery visible outside.

Apartment in Chicago

4.77 out of 5 average rating, 48 reviews

Spacious Haven Near Green Line, 20mins to Downtown

Nestled in the charming, tree-lined streets of West Woodlawn, this cozy spot invites you to explore the best of Chicago! Just steps away from the serene Washington Park, complete with playgrounds, serene hiking trails, and a lovely pond that’s perfect for a morning walk or some quiet reflection. Craving a taste of Hyde Park’s vibrant culinary scene? You’re just minutes from its top restaurants. With the Green Line train just a quick 7-minute walk away, you can be downtown in no time!

Guest favorite

A cozy living area features two large windows allowing natural light to fill the space. A fold-out futon sofa and a black armchair are positioned around a wooden coffee table. An adjacent kitchenette with a two-seat dining table is visible, along with various plants enhancing the atmosphere.

Apartment in Chicago

4.93 out of 5 average rating, 118 reviews

Spacious 1BR Garden Apt & Parking

Welcome to our tranquil garden apartment on a quiet residential street near the university and all Hyde Park attractions. Enjoy morning light through picture windows in the spacious living room and adjacent kitchenette. Breakfast on the patio or garden bench on a sunny morning. Stroll to one of 20+ eateries within four blocks. We are on-premises hosts and owners, available for whatever may arise. Access is private via back gate just off the parking lot with reserved parking space.

Guest favorite

A well-appointed bedroom features a cozy bed with a dark patterned blanket, complemented by decorative pillows. Natural light enters through a window, creating a bright ambiance. A stylish bedside lamp and a small nightstand add functionality to the space, alongside a decorative wall art piece.

Apartment in Chicago

4.79 out of 5 average rating, 118 reviews

Best Location in Hyde Park apartment

Lovely 2 bedroom apartment in Hyde Park location. Within one block of the U of Chicago. The lake is within a 10min walk. Close to the science museum, Metra, restaurants, parks, and famous Japanese garden. Updated unit was remodeled last year for you to enjoy. Separate living/dining rooms. The dinning room has a large table for you to enjoy a meal or get some work done. Great view to the park and tennis courts and porch on the kitchen to enjoy breakfast outside. Parking available.

Guest favorite

The front exterior of a modern multi-level building is shown, featuring large windows and a mix of wood and grey siding. A fenced yard with green grass is visible, along with a walkway leading to the entrance. Trees offer shade in the vicinity.

Apartment in Chicago

4.92 out of 5 average rating, 83 reviews

Comfy Solar & Green 2BR Near Hot Hyde Park!

Hi, traveler! We're so happy to host you in our unique, private 2-bedroom garden unit that's powered by the sun. It's all electric, uses no gas and is U.S. DOE Zero Energy and Energy Star® certified! You'll also have a full kitchen, full bathroom/shower, washer/dryer, living room, work area, generous closet space, and complete privacy. Your children are also welcome. We're centrally located on a quiet, residential street in safe and lovely Woodlawn near hot Hyde Park!

Guest favorite

A spacious living area is furnished with two comfortable sofas and an armchair. A central coffee table rests on polished wooden floors. A built-in bookshelf displays decorative items, and a fireplace adds character, complemented by a wall-mounted television above.

Apartment in Chicago

4.94 out of 5 average rating, 536 reviews

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

This will likely be the largest condo you have ever seen. This condo is 5 mins from the University of Chicago and the University of Chicago hospital. You will be a quick 10-15 min uber ride from downtown and 5 mins from beautiful Lake Michigan. We are currently only booking out of town travelers. We are not doing parties or events. I live in the building so if you are trying to have a party I will have it shut down and you will be asked to leave within an hour.

Guest favorite

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.

Apartment in Chicago

4.87 out of 5 average rating, 277 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.

Top guest favorite

A green sofa is positioned in a bright living area, accompanied by a round coffee table. A decorative bowl and a potted plant sit atop the table, while a piece of wall art featuring a tree landscape adds character. Natural light enters through nearby windows.

Apartment in Chicago

4.99 out of 5 average rating, 239 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.