Vacation rentals in South Side

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Top-rated vacation rentals in South Side

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Top guest favorite

A comfortable living area features a dark sectional sofa positioned around a round coffee table. A wall-mounted television is displayed above a modern electric fireplace. Natural light enters through a small window, while a plant and a workspace are subtly included in the room.

Guesthouse in Chicago

5 out of 5 average rating, 18 reviews

Garden Retreat in Historic Bronzeville

Welcome to your home away from home in historic Bronzeville! This private basement unit sleeps 3 with one queen bed and a fold-out couch. Enjoy a full bathroom, private entrance, and everything you need for a comfortable stay. Located near McCormick Place, Chinatown, museums, the lakefront, public transit, and just minutes from downtown. Whether you're here for work or relaxation, we'd be happy to host you! Washer & dryer No chores No dishwasher Early check-in, late check-out if available

Guest favorite

A well-maintained outside space features a neatly trimmed grassy area along a pathway, flanked by vibrant greenery and flowering plants. On one side, a wooden deck with railings enhances the exterior of the two-story building, while a fence provides privacy.

Apartment in Chicago

4.9 out of 5 average rating, 193 reviews

Royal Coach House Cottage

Royal Coach House Cottage- Nestled in Bronzeville community and nearby Historic Hyde Park neighborhood that is safe and family oriented. Our space is quite cozy, quaint and ideal for relaxation, peace & quiet. Flower and vegetation garden landscape. Centrally located 1.5 miles from lake front, nearby shopping, movie theater, and restaurants. Seconds from park, walking track and playground. Minutes from downtown and Magnificent Mile. Local transportation accessible including bicycle rental.

The exterior of a modern high-rise building is visible, featuring large glass windows and a curved architectural design. Surrounding trees line the street, creating a blend of urban and natural elements. The image showcases the building's height against a clear blue sky.

Apartment in Chicago

4.8 out of 5 average rating, 319 reviews

Kasa | Studio, Walk to Grant Park | South Loop

It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

Superhost

A private backyard space is visible, featuring a green lawn and paved path surrounded by various potted plants. Outdoor seating is arranged around a table shaded by a tree, while a grill stands ready for use against the wall of the guesthouse.

Guesthouse in Chicago

4.91 out of 5 average rating, 354 reviews

Private Studio in Bridgeport, Chicago

A bright studio guesthouse, perfect for business travelers, a couple’s getaway, personal retreat, or a solo adventurer. Has a kitchen sink, cabinet space for your non-perishable items, a microwave, mini-fridge, and Keurig. We provide plates, flatware, mugs, and glasses. The studio offers the privacy of your own bathroom and shower facilities. You'll rest well in a full-size Murphy bed, with sufficient storage for all your travel items. A couch is available for a third guest if needed.

Superhost

A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.

Apartment in Chicago

4.82 out of 5 average rating, 797 reviews

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Guest favorite

A modern three-story condominium is showcased, featuring a combination of dark and light brick with large windows. Soft lighting highlights the front entrance and landscaped gravel area, providing a contemporary appeal. Neighboring buildings are visible in the background, contributing to the urban atmosphere.

Condo in Chicago

4.92 out of 5 average rating, 180 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

The space has been intentionally designed to offer a modern, yet comfortable feel for individual guests or families. Conveniently located just 6 miles south of Magnificent Mile, 5.6 miles from Navy Pier, 1 mile to Lake Shore Drive, 1.5 miles from the University of Chicago, 2 miles from Museum of Science and Industry, 1.2 miles from the many restaurants on 53rd Street in Hyde Park and close to many Chicago favorites! On-street parking available directly in front of the building.

Guest favorite

A spacious living room is displayed, featuring a large sectional sofa adorned with decorative pillows. A glass coffee table rests on a patterned rug, while creative wall art and a wooden sculpture enhance the atmosphere. Soft lighting from a ceiling fan provides a warm ambiance.

Apartment in Chicago

4.98 out of 5 average rating, 43 reviews

Private Duplex w/ Theater + Games | Near UChicago

Enjoy our spacious 2-level home this fall and winter, perfect for families and groups. The lower level is your entertainment hub with a 120" projector, retro arcade, ping pong, board games, reclining sectional, 1 bedroom, and 1 bath. Upstairs features two bedrooms, a full bath, an electric fireplace for cozy nights, a fully stocked kitchen with coffee, and a furnished patio. Kids and young adults especially love the fun setup, making it a memorable Chicago stay for all.

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, 124 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 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, 281 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.

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, 20 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

Apartment in Chicago

5 out of 5 average rating, 8 reviews

Sky-High Living: Lake Views, Elite Experience

Ascend to 'The Observatory', a brand-new 3-bedroom luxury apartment on the 60th floor, where spectacular lake views meets a unique, front-row view to Grant Park & Monroe Harbor directly from your private balcony. This exclusive residence, nestled within one of Chicago's best new buildings—an art gallery unto itself—provides truly unmatched amenities and a location at the city's cultural epicenter, ensuring an unforgettable stay.

The open living space is equipped with a modern kitchen featuring dark cabinetry and stainless steel appliances. A comfortable gray couch with decorative pillows is complemented by two bright yellow chairs. A Smart TV is mounted on the wall, providing entertainment options.

Apartment in Chicago

4.79 out of 5 average rating, 52 reviews

W3N NexttoUniversityTrainPark 15minsDowntown Desk

☞ 1 Smart TV ☞ Fully equipped + stocked kitchen ☞ Self check-in ✭“Everything I needed to have a great vacation thank you ” ☞ Luggage storage available ☞ Onsite washer + dryer in basement ☞ Air conditioning 》30 mins to airports 》15 mins to Downtown Chicago 》 Walking distance to University of Chicago, L train, Park 》15 mins to McCormick Place convention, Millennium Park, museum campus 》Sleeps 6 》2 bedroom 》1 bathroom