Vacation rentals in Bridgeport

4.95 out of 5 average rating, 135 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, 159 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-lit bedroom features a spacious bed with white bedding against a backdrop of light grey walls. A wooden nightstand with a lamp is positioned beside the bed. Mirrored closet doors reflect the space, while a tall plant adds a touch of greenery.

4.88 out of 5 average rating, 83 reviews

Bridgeport Place -free parking, McCormick-Sox Park

Experience the charm of the Bridgeport neighborhood in this cozy 1 bedroom private apartment located on a peaceful tree-lined street. The apartment accommodates up to 4 guests with a sofa sleeper. Enjoy free street parking in an un-zoned area, as well as easy access to public train and bus stops nearby. Explore popular nearby attractions such as downtown, Chinatown, Sox Park, and McCormick Place. Please note that one pet per reservation is allowed with advance notice, and a fee of $20 per night

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.

4.96 out of 5 average rating, 27 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

The living area features an original tile floor complemented by green tin walls and ceiling. A brown leather sofa is positioned alongside wooden armchairs, and a circular coffee table occupies the center. A large mirror reflects light from the windows, enhancing the space's openness.

5 out of 5 average rating, 28 reviews

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.

Guest suite in Bridgeport

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.

4.89 out of 5 average rating, 19 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.

4.69 out of 5 average rating, 59 reviews

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

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.

4.91 out of 5 average rating, 354 reviews

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

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, 335 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.

5 out of 5 average rating, 86 reviews

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

The Oasis / Free street parking

Quiet home in a 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*

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, 21 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.