Holiday rentals in South Side

4.92 out of 5 average rating, 121 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

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.

4.92 out of 5 average rating, 71 reviews

Guest house 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.

5 out of 5 average rating, 34 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

Apartment 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!

4.75 out of 5 average rating, 327 reviews

Bright & Spacious| Free Parking |Trendy Bridgeport

Step inside and be greeted by an open-concept space bathed in natural light. High ceilings, hardwood floors perfectly blend vintage charm with modern elegance. The living area invites you to unwind after a day of exploring our vibrant city. Relax on the sofa, watch your favorite shows on our large flat-screen TV, or indulge in book in the cozy seating nook. Whether you're a solo traveler, couple, or friend group looking for an unforgettable adventure, this is the ultimate urban retreat.

4.91 out of 5 average rating, 163 reviews

Apartment 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, 109 reviews

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.

4.93 out of 5 average rating, 45 reviews

Guest suite in Chicago

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.

4.87 out of 5 average rating, 263 reviews

Spectacular Pilsen Studio for 2!

This chic studio in the heart of Pilsen is the perfect space to kick back and relax during your visit to the Windy City! The vibrant neighborhood always has something to offer to any type of traveler, and it's a quick trip to see most of the iconic Chicago sights. Easily walk to historic Thalia Hall, or drive to the Loop in just 5 minutes! You'll love the thoughtful touches and modern decor in the apartment, as well as the bright and welcoming main space.

5 out of 5 average rating, 8 reviews

Home in Chicago

The Modern Muse of Chicago! Close to everything!

Newly remodeled home. Art, luxury, and location!!! Enjoy a luxurious stay in this stunning 3-bedroom, 2.5-bath greystone near Chicago's top attractions. Basement unit of the home is separate and it is occupied. Relax in the king-size primary suite, work in the dedicated office, and enjoy two outdoor spaces. Street parking is free, and garage access is available. Perfect for those seeking a blend of comfort and convenience in the city!

4.7 out of 5 average rating, 271 reviews

Sonder Onterie | King Studio Apartment

Welcome to Onterie, where modern style meets an unbeatable location in the heart of Chicago's Magnificent Mile. You'll have world-class shopping and award-winning dining at your fingertips. Each apartment includes a fully equipped kitchen, in-suite laundry, and a Roku to stream your favorite shows. Unwind in the outdoor courtyard, or find focus in our co-working space. Onterie offers the perfect blend of city and lakeside living.

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Popular amenities for South Side holiday rentals

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Other great holiday rentals in South Side

4.72 out of 5 average rating, 39 reviews

Bees Knees - Room 3

MikaylahRating, 5 stars2 weeks ago

I really enjoyed my stay here . Genova place is very affordable, well kept for a shared space . I like that everything was organized . Toiletries such as body soap , hair conditioner was provided as well as towels and linens . Genova was able to accommodate me as well with some plans that didn’t quite work out with my airfare . I was very grateful and appreciative of that as well . Very good and timely with communication on whatever I needed . I’m sure a future stay here will be planned out . Maybe sooner than later . Great host . Until next time …

4.85 out of 5 average rating, 119 reviews

Hyde Park/UC Newly Renovated Private Room #1

MarcianoRating, 5 stars1 week 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!

4.87 out of 5 average rating, 46 reviews

Yellow Room - South Shore Bungalow

GavinRating, 5 stars4 days ago

What a lovely place to stay. Lady Delia showed us her turtles and had a beautiful cat. She was very friendly and talkative. She drove us to get bus passes when we didn’t know where to get them. Jeffrey jump was a convenient bus to get from her place to the city very quickly. The bathroom had the window creaked open which made it smell like the coast in the mornings. The house is a historic bungalow which gave it a very different look and feel from what I’m used to. Spent some beautiful morning strolls along the neighborhood and got to see the beautiful architecture in the city; overall was worth what we paid.

4.8 out of 5 average rating, 110 reviews

Quiet Room #5

RubenRating, 5 stars1 week ago

Silvia was great to work with and such a gracious and helpful host. I would stay again at Silvia’s location in a heartbeat!

4.75 out of 5 average rating, 4 reviews

Confortable and affordable

Said OmarRating, 5 stars1 week ago

the stay with Eduardo was very peaceful , quite and relaxing. I enjoyed it alot...

4.85 out of 5 average rating, 13 reviews

Quiet and relaxing kind bed

ManevaRating, 5 stars4 weeks ago

Very clean, had all amenities, and everything works. Highly recommend.

Superhost

4.8 out of 5 average rating, 5 reviews

room with Queen bed, work desk and dresser

ElsieRating, 5 stars2 weeks ago

We had a lovely time at Aminata’s place, who was always so helpful and responsive. The area is near a train station into the centre of the city, and the neighbourhood is quiet. We would come back and stay again.