Kid-friendly vacation rentals in Bridgeport, Chicago

Farmhouse of the Future (low clean fee, no chores)

Vintage maximalism meets hi-tech in this one-of-a-kind relaxing getaway. Far from trouble and noise but close to parks, summer fests, the loop, the White Sox, Obama library & more. Enjoy tall ceilings + rare amenities (heated bathroom floor, smart lights) and more suprises! No Costco shampoo or generic decor here. The eclectic and interactive design will stimulate kids and adults alike, and you may leave with inspiration for your own home. I am happy to customize the space to suit my guests :)

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

Al Capone Era Speakeasy 3 BRs

Located in Bridgeport, the geographic center of Chicago, this former Al Capone era speakeasy / tavern has been lovingly transformed into a 3 bedroom apartment. The amazing original tile floor, tin walls, and tin ceiling remain intact. Imagine the stories this place could tell! Bridgeport, one of the hottest neighborhoods in Chicago, is 15 minutes from downtown, 15 minutes from the beach, 5 minutes from Chinatown, and home to many restaurants, coffee shops, night life, Sox Park, and much more.

Animal House near Sox stadium

Whether your traveling with your pet or just miss a furry companion and need a loaner (just ask). Animal House is very Fur Friendly destination. Must love dogs AND cats to enter ;) There is a Small Petcare company on site. You won't have any interaction with the pets unless requested. The dogs can be noisy when playing outside approximately 4 -5 hrs out of the day. Otherwise everyone is chill. There is a separate dog run on the side of the building for yours and our dogs to run and play.

Bright & Spacious| Free Parking |Trendy Bridgeport

Step inside and be greeted by an open-concept space bathed in natural light. High ceilings, hardwood floors perfectly blend vintage charm with modern elegance. The living area invites you to unwind after a day of exploring our vibrant city. Relax on the sofa, watch your favorite shows on our large flat-screen TV, or indulge in book in the cozy seating nook. Whether you're a solo traveler, couple, or friend group looking for an unforgettable adventure, this is the ultimate urban retreat.

WF Home Sweet Home

Located in the center of the Bridgeport area, This AirBnB is clean, tidy, cozy and comfortable. It's the first choice for visitors. Two minutes walk to 8 and 31 bus stop, 15 minutes drive to downtown, McComick Place, and it close to Chinatown and White Sox Field. In addition, you can enjoy a variety of cuisines in a few minutes' walk, including Chinese, Japanese, Korean, Mexican restaurant, Starbucks,McDonald's, Dunkin Donuts, CVS. Warmly welcome friends from all over the world

Cozy 2-King Bed Bridgeport Apartment

Two bedrooms with king sized beds and ample closet space. Smart TV with streaming capability, breakfast bar, and dining area with expandable table. Kitchen has microwave, coffeepot, dishwasher, and all cooking and dining essentials. Central heat and a/c, in-unit laundry, and access to private backyard patio. Close to Sox Park, Soldier Field, McCormick Place, and many other downtown attractions. Easy access to multiple major highways and ride shares, as well as Orange Line.

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

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.