Holiday rentals in South Side

Bike the Lakefront from a Sleek 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.

Luxury Condo | Spa Bath | Full Kitchen | FREE PRKG

Enjoy a luxurious escape in this modern Bronzeville home where style meets comfort. Designed with contemporary finishes, cozy textures, and a serene vibe, it’s perfect for couples, families, friends, or business travelers. Easily accessible to UChicago, McCormick Place, Soldier Field, Shedd Aquarium. With quick freeway access to I-90 & Lakeshore Drive, Downtown Chicago is just minutes away! Relax, unwind, and enjoy free street parking plus all the essentials for a premium Chicago stay.

Cabin 102 at 747 Lofts

Unique space set up to be ADA accessible with wide walkways, step-free shower, bathroom grab bars, and open space beneath the sink! This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home.

Stylish Hyde Park Studio – Walk to UChi & Museums

Discover your Hyde Park hideaway! This sleek and cozy studio offers everything you need for a comfortable stay—stylish furnishings, a comfy queen bed, fast WiFi, and a smart TV for easy streaming. Whip up simple meals in the well-equipped kitchenette before heading out to explore. Just minutes from the University of Chicago, the Museum of Science & Industry, and the lakefront, you’ll also find cafés, restaurants, and shops right outside your door. Downtown is only a quick train ride away!

West Loop Urban Chic Coach House

Welcome to this historic neighborhood in Chicago, a cultural tapestry, rich in history and bursting with energy. Enjoy strolling along the streets lined with historic buildings, savor diverse culinary delights. Bronzeville is not just a place to stay; it is a community experience Enjoy, this one-bedroom, full bathroom historic coach house with a full kitchen, smart TV, and dedicated living space. Unwind in comfort with an in-unit washer/dryer. Plenty of street parking available.

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.

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.

Cozy newly renovated apartment in Bridgeport

Welcome to your perfect home away from home in Bridgeport, Chicago 🏡 This newly renovated cozy 1-bedroom, 1-bathroom apartment offers a comfortable, inviting space just 10 mins to downtown Chicago. Located couple minutes from Chinatown Whether you're here to catch a White Sox game or immerse yourself in the vibrant local food scene and culture, this location is ideal for exploring the best of Chicago. FREE PARKING 🅿️ NO PARTIES.

Comfy/Private Entry & Bath/Free Parking - Win Win!

A Hidden GEM on a private block in Bronzeville, ranked one of the hottest neighborhoods in Chicago. Great for those looking to travel the city from Downtown (4 miles), to the lake (1 mile) to Hyde Park (walking distance) or those simply looking to stay in and rest in a peaceful place. Welcoming guests from near and far in this comfy studio designed specifically to host those for a great Chicago experience!

Fresh and Sunny Bed & Bath by UofC

Our private bed and bath offers high ceilings, a sunny Juliet balcony, comfy Queen bed and fresh, clean finishes, including an airy, open shower. Use us as your base for exploring the city or work as we are steps away from both public trans. and the University of Chicago. It's hard to find a more convenient location in Hyde Park! Welcome!

Private BR;Parking by UofC/HydePark

This comfortable condo is a stones throw away from Hyde Park and University of Chicago. The space is great for visiting parents, researchers or professors. Your room features wifi, and a 32" TV. Access to the"L", Uber, close to lake, 20 minutes from downtown (depending on traffic). Room can accommodate 3 (4 in a pinch)

Stylish Studio Getaway – Close to University

Welcome to your serene retreat in the heart of Hyde Park. This beautifully appointed studio apartment offers a harmonious blend of historic charm and modern amenities, perfect for solo travelers, visiting scholars, or couples exploring Chicago.