Kid-friendly holiday rentals in West Side

City-Accessible Basement Retreat

Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

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

Dwntown Mins Away/Relax & Stay! Bus/Train Friendly

Take it easy in this peaceful and cozy sleeper, central to everything Chicago has to offer and only minutes from downtown. Take advantage of all of the amenities while your here and enjoy the city night life with all of the great entertainment and restaurants Chicago has to offer. Newley rehabbed with high end appliances and fixtures that you, your significant other or family can enjoy. This relaxing vibe is one that will make it feel like a home away from home with all that it has to offer.

ENC-Chi Arts Suite Near United Center & Downtown

Enjoy a cozy stay in our garden level artist apartment below our private home as we embrace life as empty nesters. Centered in the East Garfield Park community. We’re just a 12-minute commute to downtown Chicago and 7 minutes to the West Loop, IL medical district, and United Center and three blocks from the popular Garfield Park Conservatory. Plus, conveniently located half a mile from essential amenities like grocer, fast-food, Chase bank, and Walgreens. Experience comfort and value with us!

2B Midcentury Artist Loft w King Bed

Welcome to Casa D'Mi Amá, this vibrant mid-century loft style apartment is centrally located in Little Village, one of the most vibrant Mexican-American communities and thriving shopping district in Chicago. Our community is known for its colorful murals and hundreds of Latinx-owned businesses and restaurants. We are just 4 mile away from downtown & Midway airport, three miles away from Pilsen & UIC, with public transportation right outside your door making it easy to plan your visit.

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.

Sunny Coach House in Historic Oak Park

This bright, cozy coach house is your ideal base in Oak Park. It was originally the coachman's quarters behind a 1909 Prairie-style house, now converted into guest lodging with all the modern amenities above a detached garage. The coach house is at the end of a long driveway (free parking included!) on a quiet street, in the heart of the Frank Lloyd Wright district, a short walk from trains to downtown Chicago.

Urban Oasis Getaway. 6 stops to downtown!

You will enjoy your own private, bright and roomy one bedroom apartment with a full kitchen and back deck. There is a separate bedroom with a queen size bed and 2 queen size sofa beds in the living room, a dining area, in unit laundry, and high speed WiFi. It is very close to transportation and includes everything you need for a great stay from this centrally located place.

Lincoln Park Haven: Balcony, Walk to Whole Foods

Your perfect base in Chicago awaits at 'The Elm', a brand-new 2BR apartment in Lincoln Park. Enjoy stunning views of Chicago's skyline and Lake, complemented by modern amenities including a rooftop pool and gym. This great place offers easy city access via the Red Line train station, with Whole Foods across the street and charming cafes and stores nearby.