Vacation rentals in Bridgeport

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Top-rated vacation rentals in Bridgeport

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Top guest favorite
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.
Apartment in Bridgeport
4.94 out of 5 average rating, 171 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

Guest favorite
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.
Apartment in Bridgeport
4.94 out of 5 average rating, 33 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

Top guest favorite
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.
Apartment in Bridgeport
5 out of 5 average rating, 78 reviews

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.

Guest favorite
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.
Apartment in Bridgeport
4.93 out of 5 average rating, 101 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
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, 358 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.

Superhost
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.
Apartment in Bridgeport
4.74 out of 5 average rating, 339 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.

Top guest favorite
A cozy living area is highlighted by a bright yellow sofa facing a wooden coffee table atop a patterned rug. Three framed artworks adorn the blue wall, while natural light filters through two large windows with patterned curtains. A stylish plant adds a touch of greenery.
Condo in Bridgeport
5 out of 5 average rating, 94 reviews

The Oasis / Free street parking

Comfortable home in quiet, walkable, family-friendly neighborhood with quick access to downtown! Recently rehabbed 1st floor unit. Free easy street parking, well-stocked kitchen, lush backyard. Walk to parks, coffee shops, grocery store, restaurants, White Sox. Access to red & orange line trains to downtown and tourist attractions. Quick drive to Midway Airport & McCormick Center. No dishwasher Free washer dryer No chores at checkout =) Free early check in/late checkout *if available*

Guest favorite
The building features a warm brick facade, showcasing large windows that reflect the evening sky. A welcoming entrance is complemented by a few steps leading to the front door. Flanking the structure are other residential buildings, contributing to a cozy neighborhood atmosphere.
Guest suite in Bridgeport
4.92 out of 5 average rating, 25 reviews

Skylit Penthouse | Luxe Rain Shower, Church View

Unwind in our skylit penthouse on Chicago’s historic South Side—birthplace of Pope Leo XIV—just 15 min from downtown. Enjoy a luxury rain shower, soft bamboo floors, full kitchen, and a private patio with wine-worthy views of St. Mary’s Church. Located in Bridgeport, near Pilsen’s art scene and Chinatown’s food spots. The layout is open, with a convertible couch as a second bed. We live below, greet you with snacks, and host with love—this is real hospitality, not a corporate setup.

Superhost
A modern living area features a light gray sofa facing a large TV on a low stand. A circular coffee table is situated on a black-and-white striped rug. Natural light enters through the multi-pane windows, with curtains softly framing the space.
Apartment in Bridgeport
4.85 out of 5 average rating, 123 reviews

Bright & Cozy 2 Bedroom Apt - 15 Min to downtown!

Welcome to our cozy Chicago apartment located in the historic Bridgeport neighborhood! This 2-bedroom unit is located on the first floor of a two-flat building providing a comfortable and stylish retreat for travelers to Windy City. Located just steps away from a bus stop and a 5 min drive from the CTA Orange Line which provides easy access to the Loop, downtown sights, and all of Chicago's other neighborhoods. Adjacent to popular neighborhoods such as Pilsen and Chinatown.

Guest favorite
A cozy bedroom is presented with warm wood flooring and soft lighting. A spacious bed is adorned with neutral bedding, complemented by a decorative bench at the foot. A dresser and artwork decorate the walls, while natural light filters in through small windows.
Guest suite in McKinley Park
4.9 out of 5 average rating, 123 reviews

1 bed apartment + futon room bridgeport

Located at the geographic center of Chicago! Plenty of free street parking. Very safe and ~10 min walk to the 35th Orange line and 3 blocks from the Archer bus, both go directly downtown within minutes. Brand new lower level construction unit. Comfortable spacious rooms to relax in. Closet in both rooms for your use while here. The apartment has a separate entrance, bathroom, kitchen, dining space. Enjoy your own private space in Chicago with a back patio, grill, and laundry.

Guest favorite
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.
Apartment in Bridgeport
5 out of 5 average rating, 26 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!

Guest favorite
The exterior of a modern brick building is displayed, featuring an inviting entrance with a covered porch. Stone steps lead to a wooden door, surrounded by a neatly landscaped area with seasonal decorations, including pumpkins and colorful flowers. Decorative wrought iron fencing lines the sidewalk.
Apartment in Bridgeport
4.96 out of 5 average rating, 25 reviews

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.

Popular amenities for Bridgeport vacation rentals

Quick stats about vacation rentals in Bridgeport

  • Total rentals

    180 properties

  • Nightly prices starting at

    € 17 before taxes and fees

  • Total number of reviews

    7.6K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    60 properties allow pets

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

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