Vacation rentals with beach access in South Side

A cozy living room area features a dark leather sofa facing a mounted television on a wooden media console. A round shelf displays books and plants, while a small desk and chair are positioned beside a bright window.

4.94 out of 5 average rating, 163 reviews

Blue Brick Apartment in Bridgeport - Park for Free

-600 sq.ft apartment / 2nd floor / Patio Deck -Free parking pad in rear / free street parking -Commute to Downtown: 15min (drive) / 28min (transit/train) / 22min(bike) -Walk score 93! Bike Score 92! Near Trains to Downtown!! -Gated access w/ Building video and security alarm system and noise monitoring equipment. -Kitchen is stocked w/ cookware, utensils, etc. -Washer and Dryer and Dishwasher in unit (free) -Rideshare(Uber/Lyft) / Bikeshares(Divvy) are bountiful -Safe, working class neighborhood

4.92 out of 5 average rating, 100 reviews

A well-lit bedroom features a spacious bed with a soft, green blanket and burgundy pillows. A wooden desk and chair sit near a closet with sliding doors. Two vibrant artworks adorn the wall, and a cozy area rug adds comfort to the floor.

Guest suite in Chicago

Cozy 2BD Lake Apt Near Downtown, McCormick & More

Enjoy your getaway in this cozy solar powered and eco-sustainable garden apartment 5 minutes walking to Lake Michigan where you can access beaches, bike paths, prairies, parks & more! We are less that 8 min away from downtown, the University of Chicago, Soldier Field, the Field Museum and more. Our home is located in the historic Oakland neighborhood, central to so much of what Chicago has to offer. We love welcoming guests to our garden apartment where making your stay relaxing is our pleasure

A vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.

4.92 out of 5 average rating, 134 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.

A red brick three-flat building is presented with large windows and intricate architectural details. Colorful pumpkins are arranged in the front garden, which features lush greenery and blooming flowers. A rainbow flag is displayed prominently by the entrance, adding a touch of vibrant color.

5 out of 5 average rating, 120 reviews

Andersonville 2 bed with modern kitchen + bath

Hi, we're Mike and Lora. Our beautiful Mission-style three-flat is located about 100 ft. from Clark St. in Andersonville, with great bars, restaurants, and shopping just outside our door. Half a mile east is the Red Line, which gets you right downtown, and just past that is beautiful Foster Beach. We live upstairs and are happy to offer recommendations. We love it here! The apartment was rehabbed in 2019 and features a large kitchen with tons of counter space, in-unit laundry, and queen beds.

4.85 out of 5 average rating, 170 reviews

A spacious spa room features a modern two-person jacuzzi, surrounded by elegant marble walls. The jacuzzi is designed with a clear accent panel, and amenities such as towels are neatly arranged nearby, promoting a calming and relaxing environment.

Home in Whiting

The Spa of Downtown Whiting

so close to Chicago but so far away. NEWLY REMODELED AND COMPLETELY FURNISHED. There's so much to enjoy in this incredible converted 2 flat, now a single unit. WE COMPLETELY RIPPED ON AND REDID THE ENTIRE INTERIOR. 1ST Flr-spa w/ 2 person jacuzzi, shower, continuous hot water, family room, kitchen 2nd flr, sitting room w/ TV and surround sound, 2 bedrooms, w/ bathroom and bath/shower. -FRONT BALCONY, -SPEAKERS THROUGHOUT -BLOCKS FROM THE BEACH & WOLFE LAKE -PERFECT LOCATION FOR PIEROGIFEST

A modern kitchen is depicted with a stainless-steel refrigerator and oven, complemented by a tiled backsplash. Light cabinetry provides ample storage, while a cozy couch with a blue accent pillow offers a welcoming touch. Natural light brightens the space, enhancing the functionality.

4.93 out of 5 average rating, 159 reviews

Cozy 2 bdrm near McCormick Place & Wintrust Arena

Come enjoy Chicago via our cozy apartment in the quiet yet friendly Historical Bronzeville community. We are nestled between Hyde Park and South Loop, where you will find plenty of restaurants, theaters, and nightlife. Only minutes away from McCormick Place, 10-15 min drive from downtown and 3-12 miles from all the sports arenas and airports. You can bike or walk to the nearest grocery store, park, gym, and beach. The nearest bus and/or train is 2-3 blocks away for your convenience as well.

4.87 out of 5 average rating, 149 reviews

The master bedroom features a spacious bed dressed in soft linens, with a light blanket draped across the foot. A large mirror reflects natural light, and sliding glass doors lead to a private outdoor seating area. Warm hues accompany scenic artwork on the walls.

Home in Chicago

LAVISH LINCOLN PARK Home w/ Patio +attached garage

Escape into this Lincoln Park Hidden Gem! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Gorgeous master en-suite with marble bath + walkout patio! - Fast WiFi (1200 mbps) - Very comfy beds! - Attached, private garage is huge bonus! - Red line (North/Clybourn) station 0.2 miles away (3-5 minute walk)

A comfortable living area is highlighted by a modern sectional sofa and a glass coffee table. A vibrant, abstract area rug is positioned beneath, and a large flat-screen television is mounted on the wall. A colorful artwork complements the space, contributing to the inviting ambiance.

4.96 out of 5 average rating, 118 reviews

420 at Cheltenham 4BR

If you want to experience an authentic piece of Chicago and it’s rich history, our place is a cozy spot to start and it’s just like being at home. Summertime Chicago Lake Shore Drive Beaches. Lollapalooza. Chicago Riverwalk. Concerts at Soldiers Field-Bears. Winter wonder festival. The Bean. Great for larger groups visiting looking to divide costs. Obama Library, Southshore golf course, Reggies on the Beach, Shedd Aquarium, Field Museum, Museum of Science & Industry are all within 20 minutes.

The bedroom is designed with a spacious bed centered against an accent wall featuring geometric patterns. A plush bench is positioned at the foot of the bed. Warm lighting illuminates the room, complemented by rich curtains and wooden flooring.

4.98 out of 5 average rating, 173 reviews

Elegant Suite in Gold Coast

Established in 1927 as the first headquarters for Elizabeth Arden in Chicago, the Walton Residence is located in the heart of the Gold Coast neighborhood of Chicago. Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, we are perfectly situated in the middle of the action for your Chicago adventure. ***From Sept. to beginning of Dec. 2024, there will be repairs to the exterior of the building. We do not expect this to cause major interruptions to your stay.

An open living area showcases a modern kitchenette with a geometric backsplash and stainless steel appliances. A cozy seating arrangement includes a patterned chair and a glass table atop a soft rug. A large wall-mounted TV is positioned nearby, with exposed brick adding character.

4.9 out of 5 average rating, 103 reviews

Stunning Basement Apartment w/free street parking!

This beauty is centrally located to everything! Drives: 5 minutes to the beach, 6 minutes from the White Sox stadium, 5 minutes from McCormick place, 7 mins from downtown, 10 minutes to Hyde park, & close to many restaurants, night clubs, etc. I almost forgot to mention, it’s located in beautiful Bronzeville with a huge park that is walking distance. You’ll love the neighborhood!!! The unit is equipped with everything you need, and we’re always just a message/phone call away. Free parking!

4.96 out of 5 average rating, 379 reviews

The living area features a comfortable blue sofa adorned with decorative cushions, complemented by a patterned rug. A soft pink armchair and a small round coffee table are present. A vibrant floral painting hangs on the wall, and natural light enters through the window covered by light curtains.

Guest suite in Chicago

Gorgeous, cozy 1-bedroom Suite in Andersonville

Our place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, location, complete privacy and NO cleaning fee. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.

The living area features a large gray sofa, a stylish armchair, and a modern media console with a television. Natural light filters through two large windows, providing a view of the surroundings. A small plant and decorative rug add subtle touches to the space.