Vacation rentals in Bridgeport, Chicago

4.95 out of 5 average rating, 125 reviews

An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.

Home in Bridgeport

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard with exceptional landscaping. The property has a car port in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! NO CHORES! Please reach out with any questions you may have before booking Hot tub 5-6 Person Spa

A cozy living room area features a dark leather sofa facing a mounted television on a wooden media console. A round shelf displays books and plants, while a small desk and chair are positioned beside a bright window.

4.94 out of 5 average rating, 149 reviews

Blue Brick Apartment in Bridgeport - Park for Free

-600 sq.ft apartment / 2nd floor / Patio Deck -Free parking pad in rear / free street parking -Commute to Downtown: 15min (drive) / 28min (transit/train) / 22min(bike) -Walk score 93! Bike Score 92! Near Trains to Downtown!! -Gated access w/ Building video and security alarm system and noise monitoring equipment. -Kitchen is stocked w/ cookware, utensils, etc. -Washer and Dryer and Dishwasher in unit (free) -Rideshare(Uber/Lyft) / Bikeshares(Divvy) are bountiful -Safe, working class neighborhood

A well-maintained exterior of a single-story home is illuminated at night, highlighting its blue façade and inviting front porch. A decorative iron fence surrounds a small garden area, showcasing landscaped plants and soft ground lighting. Nearby, neighboring brownstone structures create a warm, community atmosphere.

5 out of 5 average rating, 67 reviews

Urban Cottage

For your Chicago visit, 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 Mars 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.

A comfortable seating area features a plush sectional sofa adorned with soft throw pillows. Light beige cushions contrast against the deep green walls. A large television is mounted opposite the seating, while sheer curtains frame the window beside a door that leads outside.

5 out of 5 average rating, 15 reviews

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

A comfortable living area is highlighted by a light gray sectional sofa and a white coffee table, placed on a textured gray rug. The kitchen area is visible in the background, featuring wood cabinets and modern appliances, enhancing the space's functionality.

4.92 out of 5 average rating, 83 reviews

Prime Bridgeport - McGuane Park

Located by Halsted Orange Line in Bridgeport, our Airbnb has is CENTERED around all the action in the neighborhood; surrounded by Grocery Stores, Fast Food, Drug Stores, Restaurants, and Iconic Parks. With a short commute to the Loop, UIC, Chinatown, we are especially sustainable for longer-term tenants! Enjoy the luxury of firm memory-foam mattresses and pillows and High-speed Internet, Central Heat and A/C and unlimited complimentary coffee for an amazing stay! 1 Queen Bed 1 Full Bed

Superhost

An open living space features soft bamboo flooring, accented by a modern couch. Natural light streams through a skylight and two gabled windows. A decorative wall clock adds charm, while a potted plant complements the serene atmosphere. The adjacent sleeping areas are visible in the background.

Guest suite in Bridgeport

4.87 out of 5 average rating, 15 reviews

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.

Superhost

A bright living space features an orange sectional sofa adorned with decorative cushions. Colorful wall art creates visual interest, while a small kitchenette with a bar height table and stools is visible. Natural light filters in through large windows, complementing the warm wood floors.

Home in Bridgeport

4.71 out of 5 average rating, 56 reviews

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.

Superhost

A private backyard space is visible, featuring a green lawn and paved path surrounded by various potted plants. Outdoor seating is arranged around a table shaded by a tree, while a grill stands ready for use against the wall of the guesthouse.

Guesthouse in Bridgeport

4.91 out of 5 average rating, 351 reviews

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.

A bright living space features a dark brown sofa adorned with orange cushions. A stylish coffee table sits on a patterned area rug, while two large windows allow natural light to fill the room. A corner mirror reflects the sofa and a cozy bed is visible in the background.

4.74 out of 5 average rating, 330 reviews

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.

A cozy living area features a spacious sectional sofa in a dark fabric, arranged with various cushions. A low table rests on the floor, while a TV is positioned on a wooden stand. Natural light filters through a window with textured glass, creating a warm ambiance.

5 out of 5 average rating, 16 reviews

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!

A spacious living area is shown, featuring a sectional couch with dark blue upholstery. A coffee table sits at its center, while a large television is positioned against the wall. Natural light enters through the adjacent windows, enhancing the neutral tones of the room.

5 out of 5 average rating, 36 reviews

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.