Vacation rentals in South Side

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Top-rated vacation rentals in South Side

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

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Guest favorite

Private room in Chicago

4.93 out of 5 average rating, 115 reviews

Festive Graffiti Pop-Art | 1PBR | Wicker Park

The apartment is wonderfully spacious, bright, and airy with soaring seven-foot windows that have an amazing view of downtown. The place is kept clean, tidy, and organized. All the amenities for a comfortable stay are provided (see list). This “Shared Listing” is a value option where you save costs by sharing common area space with other guests staying in separate lockable bedrooms. Also, the building is conveniently located near the train station giving easy access to other areas of Chicagoland

Superhost

A spacious studio is adorned with colorful artwork on the walls, offering a mix of vibrant hues. A well-made bed is positioned alongside a comfortable seating area. Bright natural light filters through the windows, illuminating the modern décor and inviting atmosphere.

Apartment in Chicago

4.68 out of 5 average rating, 34 reviews

VlP STUDlO - 3rd FLr

Welcome to our 3rd FLOOR VIP STUDIO!!! Located on the 3rd FLOOR of our charming older building. Designed to provide you the optimal comfort and relaxation after your long day. We realize, we’re not a hotel, ergo we may not be a good fit for all; HOWEVER; :) as you decide to try us out, you will not be disappointed you did!! We’re always available to you, our aim; to leave you happier and more refreshed than when you came. AND OF COURSE OUR REPEAT GUESTS GET AN EXTRA 8% OFF WHEN THEY RETURN!

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

4.76 out of 5 average rating, 50 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!

Top guest favorite

A modern living space features a light-colored sofa with decorative pillows and a woven throw. A warm-toned wooden accent wall complements a sleek electric fireplace below a mounted television. A patterned area rug anchors the room, while shelves in the background display decorative items.

Loft in Chicago

4.99 out of 5 average rating, 126 reviews

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

Superhost

Private room in Chicago

4.82 out of 5 average rating, 206 reviews

ChicagoRiver Double Room

Nicely decorated Private (10x11 sq ft) Room w/designated work station, well-lit, *shared common bathroom* (other guests may be in the premises). This is NOT a full condo rental; just 1 room. Quiet & clean, 2 miles from downtown, walking distance to dozens of restaurants in Taylor Street & Little Italy. Perfect location in a quiet neighborhood, but still close to the city to enjoy food& music festivals, free concerts in Grand Park, Museums, Broadway shows, etc

Guest favorite

A private room features a spacious bed with crisp white bedding. A wall-mounted television is situated opposite, with a small table and chair nearby. A fan is positioned to the side, and a compact refrigerator is visible next to the table. Natural light filters through sheer curtains.

Private room in Chicago

4.92 out of 5 average rating, 282 reviews

HydePark002, UC, NavyPier, Chinatown, freeparking

Feel free to check us other listings: https://www.airbnb.com/h/hydepark001 https://www.airbnb.com/h/zengarden333 https://www.airbnb.com/h/zengarden332 https://www.airbnb.com/h/zengarden001 Hyde Park luxury private room with a keypad lock on each room door. Shared full bathroom only for 2 rooms. Step to UChicago, Chicago loop, McCormick, Chinatown(hundreds of delicious food). Perfect for everyone in Chicago! Free street parking.

Guest favorite

Private room in Chicago

4.85 out of 5 average rating, 41 reviews

B: Spacious bedroom with private workspace.

Fantastic private room with a workspace. Very convenient location to restaurants and close to public transportation. Downtown is 45 minutes via public transportation. Please note that this is on the second floor and will require you to climb stairs. IMPORTANT: The other room in this apartment is shared with another guest- you cannot reserve the entire house. Kitchen, bathroom, living room are shared spaces.

Top guest favorite

Private room in Chicago

4.92 out of 5 average rating, 60 reviews

Private Home Art Gallery

Bronzeville is a center for African-American life and culture in Chicago. Historically known as the city’s “Black Metropolis,” Bronzeville has a strong sense of pride in its influential history and cultural scene. Spend the night in a home that reflects Bronzeville Art Culture. Rest and relax in a well appointed condo that feels like a home. There is plenty of free street parking.

Guest favorite

A simple bedroom is presented with a single bed adorned with a floral patterned blanket. A small wooden dresser and table are positioned nearby, while a decorative rug covers the wooden floor. Soft blue curtains frame a window, allowing natural light into the space.

Private room in Chicago

4.84 out of 5 average rating, 140 reviews

Quiet Room #3

A private room for one guest. You will find plenty of space to make it your own. The full bath and kitchen are steps away. A house full of character awaits you! Once a guest said "less is more" referring to the furniture. The room is very simple and will never feel overwhelming. My house is far from a hotel but is HOME and I welcome you.

Guest favorite

The kitchen features wooden cabinetry, stainless steel appliances, and a variety of countertop equipment. A small mat lies on the floor, and a step stool is positioned near the fridge. Natural light enters through a window, complemented by potted plants on the countertop.

Private room in Chicago

4.93 out of 5 average rating, 163 reviews

Private BR;Parking by UofC/HydePark

This comfortable condo is a stones throw away from Hyde Park and University of Chicago. The space is great for visiting parents, researchers or professors. Your room features wifi, and a 32" TV. Access to the"L", Uber, close to lake, 20 minutes from downtown (depending on traffic). Room can accommodate 3 (4 in a pinch)

Top guest favorite

A welcoming living room features a large wooden table surrounded by plants and comfortable seating. Natural light floods the space through expansive windows, enhancing the earthy tones of the decor. A cozy sofa and a vintage armchair create an inviting atmosphere for relaxation.

Private room in Chicago

4.96 out of 5 average rating, 516 reviews

Private room w/bath in urban canopy

Private bedroom w/attached private bath in a gorgeous 3-bedroom/2-bath apt on the only curvy street in Hyde Park. Common entrance and living spaces, shared with an artist who uses two bedrooms - one as studio. Enjoy the lush light-infused top floor of a turn-of-the-century urban tree house.

Guest favorite

A bright, airy bedroom features a colorful bedspread draped over a spacious bed. A window allows natural light to enter, complemented by a ceiling fan overhead. A small desk with a pink chair and bookshelves are visible against the wall, providing a functional workspace.

Private room in Chicago

4.99 out of 5 average rating, 71 reviews

Chic Comfort by UChicago Campus!

Kick back and relax in this calm, stylish space only a 6-minute walk from the University of Chicago campus. Walk to a full-scale grocery store, multiple bus lines, and the Green Line CTA. Perfect for traveling professionals, rotating medical staff, or students and family of UChicago!