Holiday rentals in Bridgeport

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

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

Urban Cottage

For your Chicago trip, book at the Urban Cottage. You'll feel relaxed and worry-free in this tidy, well-stocked space. Blocks from cafes, restaurants, and bars, Ramova Theatre, White Sox stadium, and Marz Brewery. The South Loop and Museum Campus are less than 15 minutes by car, as well as Chinatown, McCormick Place, U of Chicago and more. Buses, trains, and bicycle rentals are within walking distance. Free street parking included. Have fun and relax in Chicago's leafy Bridgeport neighborhood.

Urban Penthouse- Lux Rain Shower, Church View

Explore Pope Leo XIV’s hometown South Side of Chicago in luxury, with our unique penthouse with an all-new kitchen, a luxe rain shower, and soft bamboo floors made for barefoot lounging. Unwind on your private patio with a historic church view and a glass of wine. The convertible couch adds a second bed, and just 15 min from downtown in a quiet, safe, family-friendly neighborhood. We live below, greet you with snacks, and host with love—no corporate setup, just real hospitality and care.

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.

Private Studio in Bridgeport, Chicago

A bright studio guesthouse, perfect for business travelers, a couple’s getaway, personal retreat, or a solo adventurer. Has a kitchen sink, cabinet space for your non-perishable items, a microwave, mini-fridge, and Keurig. We provide plates, flatware, mugs, and glasses. The studio offers the privacy of your own bathroom and shower facilities. You'll rest well in a full-size Murphy bed, with sufficient storage for all your travel items. A couch is available for a third guest if needed.

Cozy Bridgeport Apartment

This cozy apartment on a quiet Bridgeport block offers comfort and convenience. The primary bedroom has a king bed, walk-in closet, and en-suite bath; the second bedroom has a queen bed and nearby full bath. Enjoy a large sectional, 55” TV, full kitchen, WiFi, and in-unit laundry. Walk to Rate Field, Bridgeport Art District, coffee shops, bars, and restaurants. Close to UIC, IIT, Chinatown, the medical district, and Pilsen. Just 15 minutes to downtown. Perfect for any stay!

Bridgeport Garden Studio

We completed a brand-new renovation of this basement apartment in 2024. It's compact, but modern and super clean! The building is a classic Chicago 3-flat, owner occupied , on a quiet street in the south-side Bridgeport neighborhood. Free washer and dryer in the rear utility room. Walking distance to Sox Park . 20 minutes by Uber to downtown Chicago. If you have a car, there is ample, free parking available on our street. One city block to the landmark Ramova Theater.

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.