Family-friendly vacation rentals 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.

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 TV, 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), Navy Pier, Obama Library, Millennium Park, Beach (1 mile), Museum, & Sports arenas.

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.

A space crafted for comfort and intentional stays.

A calm, light‑filled suite in the heart of Pilsen, made for comfort and staying with intention. A kitchen built for everyday cooking. Fast Wi‑Fi. A dedicated workspace built for long days of focus. The bedroom stays calm and dark. The living area holds your everyday routines. The art throughout adds warmth and character. Walkable to cafés, the Pink Line, the Medical District, and McCormick Place. Made for travel nurses, remote workers, creatives, and anyone settling in for more than a weekend.

The Ashlin House.

Stay at our family-friendly home on a quiet, cobblestone street on vacation or business. We've recently repainted the exterior and painted the master BR. Walking distance to quaint Downtown Whiting , Lake Michigan, Whihala Beach & Lakefront trails. The Horseshoe Casino, Wolf Lake & Pavilion, Hammond Sportsplex, Calumet College, PNW, IUN, U of Chicago, BP, & golf courses are a short drive. See Chicago's Skyline at Lakefront Park. Chicago's attractions & Hard Rock Casino are < 30 mins away.

Guesthouse | Near public transit and Lake front

A unique 400 sqft loft with bright open concept, large windows, full kitchen, and private access located in the historic Kenwood/Hyde Park area. Public Transit - 5 min walk Lake - 10 min walk Obama Presidential Library - 1.8 miles University of Chicago - 2 miles Museum of Science and Industry - 2.8 miles McCormick Place 3.4 miles Millennium Park - 6 miles Navy Pier - 6.7 miles Hyde Park restaurants! Perfect for individuals or couples, access to expressways to get anywhere in the city.

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.

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. This is our home, so we are mostly upstairs or nearby if needed. Access is private via back gate just off the parking lot with reserved parking space.

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.

Lovely 1-bedroom serviced apartment near Museums!

Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

This will likely be the largest condo you have ever seen. This condo is 5 mins from the University of Chicago and the University of Chicago hospital. You will be a quick 10-15 min uber ride from downtown and 5 mins from beautiful Lake Michigan. We are currently only booking out of town travelers. We are not doing parties or events. I live in the building so if you are trying to have a party I will have it shut down and you will be asked to leave within an hour.

Peaceful Modern Full House in Trendy Bridgeport

Kick back & relax in your home away from home in our modern & peaceful space in the heart of the Bridgeport neighborhood. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located on popular Morgan Street, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.