Condo vacation rentals in South Side

4.9 out of 5 average rating, 164 reviews

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!

ValueLocationLaundry

4.83 out of 5 average rating, 162 reviews

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.

ValueLocationCleanliness

4.98 out of 5 average rating, 171 reviews

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.

LocationFamilyLaundry

4.93 out of 5 average rating, 178 reviews

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.

ValueFamilyKitchen

4.92 out of 5 average rating, 283 reviews

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.

FamilyValueNearby

4.99 out of 5 average rating, 223 reviews

A spacious living area displays hardwood floors and elevated ceilings. A large flat-screen TV is mounted above a decorative brick fireplace. Natural light filters through multiple windows, illuminating the contemporary furniture arrangement that includes a soft sectional sofa and accent chair.

Condo in Lincoln Park

1,800ft² Parking Workspace W/D Full Kitch

• 1,800ft² | 167m² . My home is on the top floor of a four flat Brick Building . You have 3 flight of stairs to climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport Note: The fireplace is non working

ValueFamilyCleanliness

4.93 out of 5 average rating, 297 reviews

Condo in West Side

The Upscale Getaway Near Downtown

This cozy apartment features custom furniture in every room and a fireplace to warm up next to on a chilly night. Make use of the well-stocked kitchen to cook a hearty breakfast before setting out to explore the city! The primary bedroom has a King Bed, the second bedroom as queen bed and the pull out sofa in the living room has a queen bed. All of the mattresses are high quality memory foam. Parking: 1 gated parking spot included & plenty of free street parking

LocationFamilyLong stay

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!

FamilyValueParking

4.88 out of 5 average rating, 229 reviews

4.87 out of 5 average rating, 294 reviews

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.

LocationFamilyCheck-in

4.95 out of 5 average rating, 175 reviews

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.

LocationFamilyAir conditioning

Condo in Ukrainian Village

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.

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!

ValueLocationAccess

4.85 out of 5 average rating, 365 reviews