Condo vacation rentals in South Side

Find and book unique condos on Airbnb

Top-rated condo rentals in South Side

Guests agree: these condos are highly rated for location, cleanliness, and more.

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Guest favorite

A spacious living area features a large sectional sofa arranged around a modern coffee table. Artwork adorns the wall above, with soft lighting enhancing the ambiance. A patterned area rug adds texture to the hardwood floor, while natural light enters through the adjacent windows.

Condo in Downtown Chicago

Two Floor Luxury 3 Bedroom Condo in Old Town

Enjoy comfort, privacy, and elevated city living in this spacious three-bedroom, top-floor duplex apartment, located next door to The Sono Chicago in the heart of Old Town Chicago. Ideal for families, groups, or extended stays, this home offers generous space, abundant natural light, and a quiet retreat above the neighborhood. Spanning two levels on the top floor, the apartment features inviting living areas, a fully equipped kitchen, and three private outdoor decks, creating multiple spaces to

4.94 out of 5 average rating, 113 reviews

Guest favorite

A modern living area features a light-colored sectional sofa adorned with blue accent pillows. A round black coffee table is positioned in the center, resting on a decorative rug. Two lamps and a piece of coastal-themed artwork complement the bright, airy atmosphere.

Condo in Bridgeport

Convenient & Spacious 3BR Condo w/Free Parking

Get cozy in this spacious 3-bedroom condo, conveniently located 3 blocks from the Halsted Orange Line overlooking Palmisano Park and only 5 minutes' drive to McCormick Place. Clean, neat, modern and comfortable, the condo offers spacious living space with an open kitchen, washer/dryer, and an outdoor balcony perfect for families and groups. Hungry? Our complex offers a few delicious high rated yelp restaurant options to fulfill your appetite. We look forward to hosting you and your guests!

4.9 out of 5 average rating, 164 reviews

Superhost

Condo in West Side

Trendy Stay Thats Close to Loop, UC & McCormick Pl

This chic yet homie 2 bedroom condo fits six guests, comes with two full/double size beds, and a fully equipped kitchen. The bathroom has a smart mirror as you get ready to paint the town red. You’ll have a living room area to put your feet up and relax while you watch TV or catch up on some work. There is an in unit washer and dryer for longer stays, or if you need to do a quick wash. Both are brand new. For those traveling with young children we have a pack and play for your youngster.

4.83 out of 5 average rating, 162 reviews

Top guest favorite

A cozy seating area features a green sectional sofa adorned with decorative pillows in various patterns. A small wooden coffee table sits at the center, topped with a book and a small plant. Exposed brick walls complement large windows dressed with dark curtains.

Condo in Wicker Park

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

4.97 out of 5 average rating, 172 reviews

Guest favorite

Condo in West Side

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Luxury 4BR/2.5BA residence featuring 3 private bedrooms and an open-concept bonus room with a queen bed and full-size bunk beds—perfect for upscale families or executive groups. The spa-inspired primary suite offers a soaking tub and rain shower with multiple settings. Enjoy a modern kitchen, stylish living room with a 76” smart TV, and a large covered patio. Located near UIC, West Loop, Chinatown, McCormick Place, the lakefront, and some of Chicago’s best dining and cultural attractions.

4.93 out of 5 average rating, 178 reviews

Superhost

A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.

Condo in Little Italy

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

4.92 out of 5 average rating, 283 reviews

Guest favorite

A well-lit living room features panoramic windows that provide expansive city views. Comfortable seating options include a blue chair and gray sofa, arranged around a coffee table atop a patterned rug. A television is mounted on the wall, enhancing the entertainment area.

Condo in The Loop

Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Beautiful views of the Park & Lake ✅ Central Location ✅ Parking garage attached to building ($15-30 / night - Operated by LAZ) ✅ FAST WIFI ✅ Comfy KING beds ✅ Rooftop Deck ✅ 1 block from Red, Orange, Green "L" subway ✅ Close proximity to Park, Soldier Field, Museums

4.84 out of 5 average rating, 177 reviews

Superhost

Condo in Ukrainian Village

Modern Chicago Movie Themed Apt

Welcome to Chicago at the Movies! An amazing fully updated apartment in the Ukrainian Village neighborhood. This midcentury modern 3 bedroom home is perfect for groups, couples, and families looking for a perfect Chicago vacation. The property is conveniently located on Grand Avenue just minutes by car, bus or train from Downtown and the Lakefront. We are also just a short 5 Minute ride to the United Center for concerts sports and more!

4.88 out of 5 average rating, 230 reviews

Top guest favorite

A comfortable living area features a plush sectional sofa and a cozy armchair. A wooden coffee table is positioned centrally, while a television is displayed on a dark media unit. Natural light enters through multiple windows, highlighting the room's stone accent wall.

Condo in South Side

A Stones Throw from U Chicago South Campus!

This spacious 2 bedroom garden unit is located in a lovely renovated vintage World's Columbian Exposition-era graystone. Located across the street from the University of Chicago campus, this comfortable and quiet unit is also within walking distance of the Obama Presidential Center, lakefront beaches, golf courses, the Museum of Science and Industry, public transportation, and Jackson Park. No pets allowed.

4.87 out of 5 average rating, 295 reviews

Guest favorite

A cozy living area features a gray sectional sofa adorned with patterned cushions. A white coffee table sits on a soft area rug, while a vase of flowers adds a touch of elegance. An open kitchen with wooden cabinets is visible in the background.

Condo in Bridgeport

Spacious 3BR Near McCormick Place + Transit

Relax and spread out in this bright, spacious 3-bedroom, 2-bath condo, perfect for families, groups, and business travelers. Centrally located and just a short walk to the metro, you’ll have effortless access to conventions, dining, and top city attractions. Whether you’re here for work or a getaway, come home to a quiet, comfortable space where everyone can unwind, recharge, and truly feel at home.

4.95 out of 5 average rating, 177 reviews

Top guest favorite

A cozy living area features a modern sectional sofa adorned with colorful cushions and a vibrant area rug. A wooden coffee table provides a natural accent, while bright artwork is displayed on the walls. Natural light filters through the window, and the main entrance is visible.

Condo in Ukrainian Village

Welcoming 2BR in Chicago's Best Neighborhood!

Hi, I'm Kathy, and I'm your AirBnb host! I'm a real person, not a management company, and this is my real home! I love my home, my city, and sharing both with others! If you are looking for an authentic Chicago experience (and authentic Airbnb experience), look no further!

4.85 out of 5 average rating, 365 reviews

Guest favorite

A modern kitchen features wooden cabinetry and a countertop complemented by a tile backsplash. A stainless steel stove and microwave are installed, along with a double sink and a dishwasher. Utensils and dishes are organized on a drying rack, contributing to a functional cooking space.

Condo in South Side

Comfy 2 Bedroom Apartment w/ Office

Located a few blocks from the University of Chicago and 1 mile west of Chicago's beautiful lakefront, this 1st floor Condo offers plenty of comfort and space. 2 Bedrooms include firm Queen-size mattress and plenty of space. Dedicated office space

4.99 out of 5 average rating, 116 reviews