Holiday houses in South Side

Cozy Kitties in the City 1BR by Park/Sox/Transit

This is my personal home in an 1890s Worker's Cottage, originally built for laborers in the Chicago Stockyards. It's offered below the going rate because looking after 2 friendly cats is part of the deal. This arrangement is not for everyone, but it comes with laughs and snuggles. Picture directions + all supplies provided. Great neighborhood with lots of green space - walk to everything you need! Super fast WiFi Free parking; Get downtown in 20 min by L train or via any of 5 nearby buses

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.

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!

Inviting Studio w/ Full Kitchen & Washer/Dryer

Escape to this modern Hyde Park studio, perfectly located near the University of Chicago, Museum of Science & Industry, and Lake Michigan’s scenic shoreline. Thoughtfully designed with chic décor, a plush queen bed, smart TV, and fast WiFi, it blends style and comfort. The kitchenette is stocked for light cooking, and the cozy layout is ideal for solo travelers or couples. Walk to trendy cafés, restaurants, and shops, or hop on nearby transit for a quick ride to downtown Chicago.

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.

Cabin 207 at 747 Lofts

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. One of the best pizza spots in Chicago is only steps away!

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!

Stylish HydePark Studio Retreat

Welcome to your stylish and comfortable studio apartment located in the heart of Hyde Park. This thoughtfully designed space offers the perfect blend of modern amenities and historic charm, ideal for solo travelers, visiting academics, or couples exploring Chicago.​

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.

BOHEMIAN LODGE #4 ( clean & affordable travel)

Pilsen neighborhood = best in Chicago!! PRIVATE SPACE - BEDROOM & ATTACHED PRIVATE BATHROOM CLICK "show more " below BEFORE YOU BOOK/INQUIRE Please read and respond to our house rules. No smoking No visitors