Vacation rentals in South Side

4.96 out of 5 average rating, 122 reviews

An inviting outdoor space features a covered hot tub beneath a wooden pergola adorned with string lights. Comfortable seating arrangements surround a fire table at the center, providing a cozy atmosphere for relaxation and gatherings.

Home in Chicago

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard with exceptional landscaping. The property has a car port in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! NO CHORES! Please reach out with any questions you may have before booking Hot tub 5-6 Person Spa

A large, reflective sculpture sits in an open area, surrounded by towering buildings that showcase various architectural styles. The sky displays a soft blend of colors, hinting at dusk. Lush greenery is visible at the base of the sculpture, adding contrast to the urban landscape.

4.92 out of 5 average rating, 120 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

5 out of 5 average rating, 9 reviews

A decorative sign reading 'VIP Lounge' is displayed against a green textured background, with a butterfly illustration placed below. The modern lettering stands out, providing a welcoming touch to the space.

Home in Chicago

“The Marlowe” A Couples Getaway

Couples Getaway: Your Ultimate Lovers Nest Welcome to Couples Getaway, an enchanting one-bedroom retreat designed for romance and relaxation. Nestled in a serene setting, this cozy haven features a luxurious six-person hot tub, perfect for unwinding under the stars. Inside, indulge in cinematic experiences with an 80-inch smart TV, equipped with all the latest movies, channels, and series. The living room boasts surround sound, allowing you to create the perfect ambiance for a cozy night in.

4.91 out of 5 average rating, 70 reviews

A compact workspace is situated near a fully equipped kitchenette. The desk, affixed to the wall, is complemented by a black office chair. An oven is integrated into the cabinetry, while a coffee maker is positioned on the countertop beside a sleek trash can.

Guesthouse in Chicago

Guesthouse | Near public transit and Lake front

A unique 400 sqft loft with bright open concept multipurpose space, large windows, full kitchen, and private access located in the historic Kenwood/Hyde Park area. Public Transportation - 5 minute walk Lakefront - 10 minute walk University of Chicago - 2 miles Museum of Science and Industry - 2.8 miles Mccormick Place 3.4 miles Millennium Park - 6 miles Navy Pier - 6.7 miles Hyde Park restaurants! Perfect for individuals or couples, great access to expressways to get anywhere in the city.

A spacious entertainment area features a large screen displaying a serene coastal image. A vibrant blue area rug is positioned on tiled flooring. Audio equipment is neatly arranged beneath the screen, complemented by framed artwork on the walls, creating an inviting setting for relaxation and enjoyment.

5 out of 5 average rating, 32 reviews

2-Story 3BR Hyde Park | Theater+Arcade | UChicago

Relax with family and friends this summer in our spacious 2-level home, equipped with central air! The lower level is your private fun zone—featuring a 120" projector for movies, a retro arcade game, ping pong, board games, a bedroom and bath, plus a NEW sectional for movie nights. Upstairs, you'll find two more bedrooms, a full bathroom, an outdoor patio, and a fully stocked kitchen with an air fryer, Keurig, and complimentary coffee. Everything you need for a fun, comfortable stay together.

5 out of 5 average rating, 39 reviews

An inviting living area features hardwood flooring and large windows allowing natural light. A plush sofa with dark cushions is complemented by a unique accent chair. A contemporary chandelier hangs from the ceiling, and a mirror is mounted on the wall, reflecting the cozy ambiance.

Condo in Chicago

University of Chicago Condo-Upgraded and Spacious

Beautiful, spacious, 1 bedrm, 2 bathrm condo near the University of Chicago. Open floorplan, hardwd floors, stainless appliances, 2 Smart TVs in bedrm & living rm, in-unit laundry, and private parking space. Features a cozy reading nook and large outdoor patio. On a quiet treelined street - minutes from Hyde Park and waking distance to Lake Michigan, Jackson Park Golf Course, the 222,000sq ft Regal Mile Film Studios, and upcoming Obama Presidential Library. Your stylish home away from home!

A communal area features comfortable seating, including a pair of gray armchairs with decorative throw pillows. A low coffee table is positioned between them. In the background, a beverage station with a coffee machine and snacks is visible, alongside a plant for added detail.

4.8 out of 5 average rating, 298 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.

4.91 out of 5 average rating, 163 reviews

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

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.

4.99 out of 5 average rating, 107 reviews

A historic stone building showcases unique architecture, featuring a turret and intricate details. Lush greenery is visible in front, framing the entrance. The property is set against a bright blue sky, enhancing its inviting appearance.

Loft in Chicago

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

Guest suite in Chicago

4.93 out of 5 average rating, 45 reviews

Classic Den @ U Chicago

Our homey space includes full bath, kitchenette, living area and super comfy Queen bed. Direct access to unit from the exterior rear door makes coming and going easy. Located on University Ave. just a minutes walk to U. Chicago campus, easy access to public transportation taking you downtown in just over half an hour. *Note*This is in the basement of our home. Interior stair door locks from basement side to ensure guest privacy. You will hear us upstairs at times.

Superhost

A spacious living area is highlighted by large windows, allowing natural light to fill the room. A wooden dining table is surrounded by multiple chairs, while a comfortable leather sectional couch invites relaxation. Potted plants add a touch of greenery to the decor.

Condo in Chicago

5 out of 5 average rating, 12 reviews

Bronzeville Oasis

Kick back and relax in this calm, stylish space in the heart of Chicago’s legendary Bronzeville neighborhood. This stylish condo is minutes away from downtown Chicago, the magnificent mile, Navy Pier, Lakeshore Drive, the University of Chicago, and the museum of Science and Industry. You can also enjoy many restaurants in the heart of Hyde Park minutes away on 53rd St. On street parking is available directly in front and beside the building.

Superhost

A spacious living area allows for abundant natural light, with floor-to-ceiling windows that offer panoramic views of Chicago's skyline and Lake. Sleek flooring complements modern furnishings, including a mounted television and a stylish console. A door leads to a private balcony.

4.82 out of 5 average rating, 39 reviews

Lincoln Park Oasis: Safe Stay, Balcony Views

Experience a comfortable stay at 'The Pine', a brand-new 2BR apartment in Lincoln Park. Enjoy stunning views of Chicago's skyline and Lake, complemented by modern amenities including a rooftop pool and gym. Its convenient access to the city via the Red Line train station, along with Whole Foods across the street and cafes and stores nearby, makes this a truly great place.

Vacation rentals for every style

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Popular amenities for South Side vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in South Side

4.85 out of 5 average rating, 118 reviews

Hyde Park/UC Newly Renovated Private Room #1

MarcianoRating, 5 stars3 days ago

Great stay at Andy's place. Listing is accurate to the description. Place is clean, private room and shared bathroom has all the essentials. Roommates were very private so I felt like I was free to stay in the common areas without much disturbances. Andy himself was very professional and responsive to my messages. Check in was very easy. I would recommend Andy's place and would definitely stay here if I am in town again for a conference. Thank you for a very peaceful and pleasant stay, Andy!

A private bedroom features a spacious bed dressed in navy blue linens, complemented by folded towels. Two art pieces are displayed on the walls, and a small desk with a chair is positioned beside the bed. Natural light enters through a window with sheer blinds.

5 out of 5 average rating, 7 reviews

S4- Small Private Bedroom

AnthonyRating, 5 stars3 weeks ago

Had a good experience here. First couple nights after I checked in the other roommates were noisy but I brought up the issue to the host and they promptly resolved it. Very responsive, and shows that they care

4.87 out of 5 average rating, 45 reviews

Yellow Room - South Shore Bungalow

JaiRating, 5 stars1 day ago

Delia’s place was very nice and clean! Would definitely book again!

4.95 out of 5 average rating, 22 reviews

A wooden door painted in a deep red hue features a sign reading 'BIRD ROOM' hanging from a string. A light yellow wall surrounds the door, complemented by a nearby shelf stacked with books and small items. A plush dog toy is perched on the shelf.

Private room in Oak Park

Bird Room - Sunny bedroom in NE Oak Park

SamRating, 5 stars1 week ago

Kris has a beautiful and cozy home in Oak Park. The whole village is lovely and walkable. I’d definitely stay again.

A modern bathroom showcases a walk-in shower with textured stone flooring and glass paneling. A small sink with sleek fixtures is positioned beside a large mirror, reflecting the neutral tile design. Warm lighting enhances the clean and functional layout.

5 out of 5 average rating, 9 reviews

Sweet Pea - Orange Key - Place 3

MelvinRating, 5 stars3 weeks ago

Great stay for what you pay will definitely book the room in the near future or on my next visit.

A compact workspace features a wooden desk with a folding chair positioned underneath. A wall-mounted television displays a streaming service interface. A small desk lamp sits on the surface, providing additional light to the setup.

5 out of 5 average rating, 3 reviews

3 min Walk to Chinatown

주호Rating, 5 stars1 month ago

economical place in Chicago! simple and comfortable! very fast communication!

Top guest favorite

A hand is positioned near a modern keypad locking mechanism, displaying numbers illuminated in blue. The keypad features a circular design, mounted on a door, providing a secure entry option.

5 out of 5 average rating, 35 reviews

Jeffery Manor - Private Room

JonathanRating, 5 stars2 weeks ago

Incredibly responsive host and even waited for me to arrive at the place past Midnight! Needless to say Deborah is a remarkable making me feel at home. 😀

The bathroom is equipped with a bathtub and shower combination, featuring a shower curtain with light blue and gray stripes. A window allows natural light to filter in. A sink and toilet are positioned conveniently, with toiletries placed on the bathtub's edge.