Vacation rentals in South Side

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Top-rated vacation rentals in South Side

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Guest favorite

A spacious living area features a dark couch adorned with a 'Chicago' pillow. A coffee table sits in front, complemented by modern black chairs. Artwork and decorative elements enhance the neutral-colored walls, while recessed lighting provides a warm ambiance.

Guest suite in Chicago

4.91 out of 5 average rating, 234 reviews

Bike the Lakefront from a Sleek Urban Retreat

Cook in a stainless-steel kitchen with granite countertops, gleaming utensils, and a well-stocked fridge. Black and gray accents and dark woods offset a muted palette at this open-concept home. Thoughtful details include 800-thread-count linens. A retreat designed to evoke relaxation through luxury and elements of the earth. Lush bath linens & robes, luxury body and hair care products, coupled with sleek design creates a spa bathroom retreat you're sure to enjoy. Full granite and stainless steel kitchen, with wine fridge, stocked with morning essentials and Bronzeville BNB staples to ease you into the day's adventure. Relax or be social in the open space living and dining area equipped with Amazon entertainment system and Wi-Fi providing up-to-date weather, sports, news, the latest movies and yes...sometimes...work. Retreat to one of three sleeping accommodations, each drept in 800 thread count, 100% cotton linens. You'll find Bronzeville BNB thoughtful touches around every corner. Enjoy! You'll have access to the full suite including open floor plan living room/dining room/kitchen, spa bathroom, bedroom with walk in closet, hall closet, rear mud room containing washer/dryer, mop/broom, garbage tray, and fire extinguisher. There is concrete patios at the front and the rear entrances also. The backyard, main property deck and garage are restricted areas. The suite is nestled in the historic Bronzeville-Hyde Park neighborhood. Rent a Divvy bike to explore the 18-mile lakefront recreation trail close by. Chicago’s main attractions are a short drive away. The most efficient way to get around the city is UBER offering door-to-door service to all of Chicago's top attractions. Claim your FREE Uber ride (up to $5) gift from the host by signing up using this link: https://www.uber.com/invite/zkyf4 Divvy bike rentals are an awesome way to explore Chicago's 18 mile lakefront trail. The Divvy Explorer Pass includes 24 hours of bike access, with unlimited trips up to 3 hours each for $15/day. Pick up and return bikes at the 575+ Chicago & Evanston Divvy stations. Download the Divvy app for station locations and ride pass purchases. Your safety is important. Please be safe and aware of your surroundings. In any huge city, things can happen. It is suggested to not walk at night, avoid public transportation outside of downtown, and use rideshare transportation apps to avoid exchanging currency.

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, 121 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.

Guest favorite

A cozy bedroom features a spacious bed with a soft white comforter. A modern television is mounted on the wall opposite the bed. A circular mirror and small table add to the decor, while a vintage-style refrigerator and a bathroom door are visible in the background.

Private room in Chicago

4.98 out of 5 average rating, 175 reviews

McCormick332, Chinatown, SOX, GrantPark, UC

Feel free to check us other listings: https://www.airbnb.com/h/zengarden001 https://www.airbnb.com/h/zengarden221 https://www.airbnb.com/h/zengarden331 https://www.airbnb.com/h/zengarden333 A new renovated luxury zen garden step to Chicago loop, McCormick Place, Millennium Park, Navy Pier, SOX, Art Institute, UIC, IIT, UCHICAGO, Chinatown(hundreds of delicious food), Midway Airport. Perfect place for everyone in Chicago! Super easy free street parking!

Top guest favorite

A spacious living area features high ceilings with a skylight and large windows, offering ample natural light. A comfortable green sofa and a black armchair are positioned near a coffee table. A fireplace and a television are visible, with scenic views seen through the glass doors.

Apartment in Chicago

5 out of 5 average rating, 17 reviews

Sunny Penthouse - Oakwood Beach

Gorgeous top floor 2 bedroom 2 bathroom condo in Bronzeville. It has high ceilings with lots of natural light. The kitchen is fully equipped with everything you need to cook a delicious meal. Plus, there are many food options nearby. Enjoy a 15 minute walk to the lake front and Oakwood beach. Centrally located near downtown, Solider Field, Rate Field, Field Museum, The Art Institute of Chicago, Chinatown, Hyde Park, and plenty more!

Guest favorite

Private room in Chicago

4.89 out of 5 average rating, 215 reviews

HydePark003, UC, NavyPier, Chinatown, freeparking

Feel free to check us other listings: 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.

A spacious sleeping area features a large bed adorned with a geometric patterned blanket. Black and white artwork decorates the walls, complemented by a standing lamp. A cozy seating area is included, showcasing patterned cushions and throws for added comfort.

Guest suite in Chicago

4.82 out of 5 average rating, 307 reviews

Comfy/Private Entry & Bath/Free Parking - Win Win!

A Hidden GEM on a private block in Bronzeville, ranked one of the hottest neighborhoods in Chicago. Great for those looking to travel the city from Downtown (4 miles), to the lake (1 mile) to Hyde Park (walking distance) or those simply looking to stay in and rest in a peaceful place. Welcoming guests from near and far in this comfy studio designed specifically to host those for a great Chicago experience!

Superhost

A light-filled studio space features a plush bed with decorative pillows, accompanied by a modern wooden dresser. A flat-screen TV is mounted on the wall, and a cozy seating area is visible nearby. The open layout includes a kitchen space in the background.

Apartment in Chicago

4.75 out of 5 average rating, 4 reviews

Peaceful Hyde Park Studio; Near UChicago & Lake

Welcome to our cozy Hyde Park studio, perfect for 2 guests! Just minutes from the University of Chicago and the beautiful lakefront, this space offers comfort and convenience in one of Chicago’s most historic neighborhoods. Explore the vibrant 53rd St strip filled with cafes, shops, and local charm. Whether you're here for study, leisure, or a bit of both, enjoy a peaceful stay in the heart of Hyde Park.

A cozy sleeping area features a yellow bedspread over a spacious bed. A large world map artwork is positioned above the bed, complemented by plants and decorative items nearby. A full-length mirror leans against the wall, reflecting the room's warm tones and wooden flooring.

Apartment in Chicago

4.83 out of 5 average rating, 30 reviews

Vintage Condo-Heart of Hyde Park

Vintage charm with a mixture of modern design. It’s clean, it’s quiet and and very cozy. Located one block from downtown Hyde Park. This studio unit is walking distance to numerous restaurants, hotels and stores. University of Chicago campus is nearby and take their shuttle bus one block away to get there quickly or to explore Hyde Park. Public transportation is also nearby approx. a half a block away.

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

4.92 out of 5 average rating, 159 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)

Guest favorite

A bright room is presented with a full-size bed featuring a navy blue coverlet and matching pillows. A small desk with a chair is positioned near the bed. A nightstand holds a small vase with a rose. Natural light filters through the window, highlighting the floral artwork on the wall.

Private room in Chicago

4.86 out of 5 average rating, 128 reviews

Hyde Park/UC Newly Renovated Private Room #1

# This bright private room is in a newly renovated townhome at Hyde Park, blocks away from University of Chicago medical center and its main campus. Free internet and free Parking on the street. Keypad on the room door is to double secure your privacy. Self check-in and check-out.