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 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!

ValueFamilyAccuracy

4.9 out of 5 average rating, 164 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.

LocationFamilyDecor

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.

ValueFamilyDecor

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.

ValueLocationBreakfast

4.92 out of 5 average rating, 283 reviews

Guest favorite

A modern living area showcases a coffered ceiling and stylish furnishings. Plush sofas and accent chairs are arranged around a coffee table, with a large wall-mounted television and a decorative painting enhancing the aesthetic. Natural light enters through multiple windows, illuminating the space.

Condo in West Town

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

ValueLocationCheck-in

4.95 out of 5 average rating, 219 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

FamilyLocationGetting around

4.84 out of 5 average rating, 177 reviews

Top guest favorite

Condo in West Loop

Fulton Market Loft | Rooftop Fire Pit | Parking

Featured in Condé Nast Traveler and Architectural Digest. Rated top 1% of all Airbnb listings nationwide. Two-level loft in the heart of Fulton Market. Soaring ceilings, floor-to-ceiling windows, gourmet kitchen with exposed brick, 3 bedrooms, 2.5 baths, in-unit laundry, and dedicated parking. Step outside to a private rooftop terrace with fire pit and panoramic skyline views. Steps from MICHELIN-recognized Taquería Chingón and Restaurant Row.

FamilyLocationHospitality

4.96 out of 5 average rating, 291 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!

LocationFamilyKitchen

4.88 out of 5 average rating, 233 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.

FamilyValueAccess

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.

FamilyValueCleanliness

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!

LocationValueLaundry

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

FamilyValueIndoor spaces

4.99 out of 5 average rating, 116 reviews