Holiday houses in South Side

Visit Obama Library & UIC from this Urban Retreat

Cook in a stainless-steel kitchen with granite countertops, gleaming utensils, and a well-stocked fridge. Black and gray accents and dark woods offset a muted palette at this open-concept home. Thoughtful details include 800-thread-count linens. A retreat designed to evoke relaxation through luxury and elements of the earth. Lush bath linens & robes, luxury body and hair care products, coupled with sleek design creates a spa bathroom retreat you're sure to enjoy. Full granite and stainless steel kitchen, with wine fridge, stocked with morning essentials and Bronzeville BNB staples to ease you into the day's adventure. Relax or be social in the open space living and dining area equipped with Amazon entertainment system and Wi-Fi providing up-to-date weather, sports, news, the latest movies and yes...sometimes...work. Retreat to one of three sleeping accommodations, each drept in 800 thread count, 100% cotton linens. You'll find Bronzeville BNB thoughtful touches around every corner. Enjoy! You'll have access to the full suite including open floor plan living room/dining room/kitchen, spa bathroom, bedroom with walk in closet, hall closet, rear mud room containing washer/dryer, mop/broom, garbage tray, and fire extinguisher. There is concrete patios at the front and the rear entrances also. The backyard, main property deck and garage are restricted areas. The suite is nestled in the historic Bronzeville-Hyde Park neighborhood. Rent a Divvy bike to explore the 18-mile lakefront recreation trail close by. Chicago’s main attractions are a short drive away. The most efficient way to get around the city is UBER offering door-to-door service to all of Chicago's top attractions. Claim your FREE Uber ride (up to $5) gift from the host by signing up using this link: https://www.uber.com/invite/zkyf4 Divvy bike rentals are an awesome way to explore Chicago's 18 mile lakefront trail. The Divvy Explorer Pass includes 24 hours of bike access, with unlimited trips up to 3 hours each for $15/day. Pick up and return bikes at the 575+ Chicago & Evanston Divvy stations. Download the Divvy app for station locations and ride pass purchases. Your safety is important. Please be safe and aware of your surroundings. In any huge city, things can happen. It is suggested to not walk at night, avoid public transportation outside of downtown, and use rideshare transportation apps to avoid exchanging currency.

Large Minimalist Garden Studio: Centrally Located

Need a cozy, unique, convenient, & affordable place to stay? Look no further, this may be the perfect spot for you! Located in the heart of Historic Bronzeville, just minutes from downtown Chicago, McCormick Place Convention Center, Illinois Institute of Technology, Sox Stadium, & only 1.2 miles from the University of Chicago, this spacious & serene retreat offers the ideal escape. Relax, recharge, and leave your worries behind in a space thoughtfully designed for your comfort and convenience.

PRIVATE 2-bedroom 1.5 bath w/ living room

Next to University of Chicago campus. Private entry to 2-bedroom/1.5-bath apartment: back half is our separate craft space and front half is your private Airbnb suite. No proper kitchen, but there is a large fridge, microwave, etc. This Airbnb is in our 4-unit apt building next to our house where we've had a 5-star Airbnb room for 10+ years as a Super Host. The other tenants are long-term lease-holders and wonderful people whom we're happy to call our neighbors on this quiet tree-lined street.

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!

Sunny Penthouse - Oakwood Beach

Gorgeous top-floor 2-bedroom, 2-bathroom condo in the heart of Bronzeville! With high ceilings and tons of natural light. The fully equipped kitchen has everything you need to cook a delicious meal, or you can enjoy one of the many great dining options nearby. 🌊Take a 15-minute walk to the lakefront and Oakwood Beach. Centrally located near: • Downtown Chicago • Soldier Field & Guaranteed Rate Field • Field Museum & Art Institute • Chinatown, Hyde Park & Pilsen • And much more!

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.

Beautifully Remodeled 2B in Historic Hyde Park

2nd-floor unit with two flights of stairs. Older building with radiant heat managed by the building. Enjoy your stay in this charming 2BR/1BA apartment in Hyde Park. Features a comfortable living area, full kitchen, and cozy bedrooms—perfect for families, friends, or business travelers. Close to the University of Chicago, Museum of Science and Industry, and lakefront parks. Easy access to dining, culture, and public transit. A great home base for exploring Chicago!

Blue Brick Apartment in Bridgeport - Park for Free

• Free street parking • Trains to Downtown!! • Fully stocked kitchen • Walk to dining & bars! • Free parking pad in rear • Noise monitoring equipment • Walk score 93! Bike Score 92! • 600 sq ft apartment | 2nd floor | Patio • Safe, working class neighborhood! • Commute to Downtown: 15min (drive) • 28min (transit/train) | 22min(bike) • Building video surveillance alarm system • Washer | Dryer | Dishwasher are included • Rideshare (Uber/Lyft) | Bikeshares(Divvy)

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

Studio in Hyde Park Near UChicago & Lake

Enjoy Hyde Park living in this bright, newly updated 400 sq. ft. studio featuring a cozy queen bed, 65" Roku TV, full kitchen with essentials, and private bath. Walk to the University of Chicago, the Museum of Science & Industry, and 53rd Street’s cafés, shops, and restaurants. With easy access to Metra, CTA buses, and the scenic lakefront, this charming space is perfect for comfort, convenience, and a true Chicago experience.

Hyde Park Haven | 2BR Retreat

Your cozy 2BR retreat in the heart of Chicago’s historic Hyde Park neighborhood. What You’ll Love: • 2 Comfortable Bedrooms – Each with a plush Queen bed for restful nights • Bathroom – Clean, modern • Fully Equipped Kitchen – Cook up a storm or enjoy takeout from local gems • Bright Living Space – Kick back, stream your favorites, or plan your next adventure • Wi-Fi + Smart TV – Stay connected or unwind with ease

Modern 2BR/2BA Condo | Spa Bath + Free Parking

Enjoy the entire condo to yourself in this clean, modern 2-bedroom, 2-bath home, designed for comfort and convenience. Perfect for couples, families, or business travelers seeking a quiet, cozy stay. Enjoy a full kitchen, spa-style bath, and free street parking. Minutes from UChicago, McCormick Place, Soldier Field, Shedd Aquarium, and quick access to I-90, Lake Shore Drive, and downtown Chicago.