Apartment vacation rentals 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, 161 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

A cozy living area is highlighted by a spacious blue sofa and a large, dark coffee table. Floor-to-ceiling windows offer panoramic views of the city skyline, while a vibrant green accent wall adds a refreshing touch. A potted plant brings a natural element into the space.

4.87 out of 5 average rating, 113 reviews

Skyline 2BR in South Loop Chicago Near McCormick

Welcome and Experience Chicago in style at our upscale corner suite nestled in the dynamic South Loop district—just steps from McCormick Place and minutes from top city landmarks. This modern, metropolitan 2-bedroom, 2-bathroom suite features soaring 10 ft ceilings, a spacious open layout, and curated interiors that set it apart from the average stay. From custom furnishings to thoughtful amenities, we’ve created an elevated home-away-from-home for families, professionals, and long-term stays.

Top guest favorite

A comfortable seating area features a plush sectional sofa adorned with soft throw pillows. Light beige cushions contrast against the deep green walls. A large television is mounted opposite the seating, while sheer curtains frame the window beside a door that leads outside.

4.93 out of 5 average rating, 29 reviews

Designer Garden Unit in Bridgeport

Welcome to Bridgeport! You're a short walk from the best coffee shops, vintage stores, cocktail bars, art galleries, parks, restaurants, and Rate Field, the home of the White Sox! The neighborhood has so much to offer! Just minutes from Chinatown, McCormick Place, and 10 minutes to downtown Chicago! Be sure to check out my guidebook for recs! I look forward to hosting you! -Free street parking -easy Uber/Lyft 24/7 -easy access to public transit -15-25 mins from Midway -30-45 mins from O'Hare

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.

4.9 out of 5 average rating, 192 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.

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, 102 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!

A bright living space features a dark brown sofa adorned with orange cushions. A stylish coffee table sits on a patterned area rug, while two large windows allow natural light to fill the room. A corner mirror reflects the sofa and a cozy bed is visible in the background.

4.74 out of 5 average rating, 337 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.

A cozy living area features two large windows allowing natural light to fill the space. A fold-out futon sofa and a black armchair are positioned around a wooden coffee table. An adjacent kitchenette with a two-seat dining table is visible, along with various plants enhancing the atmosphere.

4.93 out of 5 average rating, 120 reviews

Spacious 1BR Garden Apt & Parking

Welcome to our tranquil garden apartment on a quiet residential street near the university and all Hyde Park attractions. Enjoy morning light through picture windows in the spacious living room and adjacent kitchenette. Breakfast on the patio or garden bench on a sunny morning. Stroll to one of 20+ eateries within four blocks. We are on-premises hosts and owners, available for whatever may arise. Access is private via back gate just off the parking lot with reserved parking space.

A well-appointed bedroom features a cozy bed with a dark patterned blanket, complemented by decorative pillows. Natural light enters through a window, creating a bright ambiance. A stylish bedside lamp and a small nightstand add functionality to the space, alongside a decorative wall art piece.

4.79 out of 5 average rating, 120 reviews

Best Location in Hyde Park apartment

Lovely 2 bedroom apartment in Hyde Park location. Within one block of the U of Chicago. The lake is within a 10min walk. Close to the science museum, Metra, restaurants, parks, and famous Japanese garden. Updated unit was remodeled last year for you to enjoy. Separate living/dining rooms. The dinning room has a large table for you to enjoy a meal or get some work done. Great view to the park and tennis courts and porch on the kitchen to enjoy breakfast outside. Parking available.

A modern living area features a navy blue sectional sofa adorned with light throw pillows. A round coffee table holds a woven basket and a vase of vibrant red tulips, adding a touch of color. A piece of artwork hangs on the wall, complementing the neutral decor.

4.87 out of 5 average rating, 169 reviews

Modern 2BRD apartment| 5min to McCormick Place

Stay in a newly remodeled, spacious 2-bedroom apartment in Chicago. FREE STREET PARKING (a rare gem in Chicago!) Just blocks from Illinois Institute of Tech, a 7-8 min walk to Green/Red lines, 15 min walk to White Sox stadium, 20 min walk to 31st St Beach, and a 5 min drive to McCormick. Sleeps up to 4 with 2 private bedrooms, full kitchen, workspace, TVs & WiFi. Please note: This is a multi-unit building with long-term tenants, so occasional noise from neighbors may be heard.

A vintage-style sign featuring bold red and white lettering, stating 'Bohemian Lodge no 17' against a dark brown background. Decorative elements include images of beer glasses and whimsical knot designs, creating a nostalgic atmosphere.

4.84 out of 5 average rating, 302 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond to our house rules.

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.

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 brightly illuminated living area features a light-colored sofa adorned with decorative cushions. A modern coffee table sits centrally, while colorful artwork enhances the walls. The space opens toward a dining area, with a glimpse of the kitchen visible in the background.