Vacation rentals in Bridgeport, Chicago

4.96 out of 5 average rating, 123 reviews

An inviting outdoor space features a covered hot tub beneath a wooden pergola adorned with string lights. Comfortable seating arrangements surround a fire table at the center, providing a cozy atmosphere for relaxation and gatherings.

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 panoramic view of Chicago's skyline is displayed, featuring a variety of architectural styles. The skyline is illuminated by the warm hues of sunset, contrasting with the blue waters of Lake Michigan, while the shoreline and beach are visible in the foreground.

4.94 out of 5 average rating, 143 reviews

CitySlickers Crash Pad /Free Parking /No Clean Fee

-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 small outdoor patio area is equipped with two red adirondack chairs facing a compact gray table. A grill is positioned nearby against a wooden fence, creating a simple space for relaxation and outdoor cooking.

4.87 out of 5 average rating, 78 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

The image showcases a backyard garden area featuring lush greenery and a dining set composed of wooden benches and a table. A charcoal grill is positioned nearby. In the background, stairs lead up to a light-colored cottage with a large door, surrounded by trees and shrubs.

5 out of 5 average rating, 11 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 detailed regional map displays various neighborhoods and landmarks in the area. Key locations, travel times, and public transit routes are highlighted. The map is marked with clear labels for easy navigation, showcasing proximity to important sites like UIC Campus and Chinatown.

4.91 out of 5 average rating, 78 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

A panoramic view of a baseball field at night is captured, showcasing a well-lit stadium filled with spectators. Bright lights illuminate the diamond, while large electronic screens display advertisements, contributing to the vibrant atmosphere of a live sporting event.

4.75 out of 5 average rating, 327 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, 76 reviews

An outdoor patio area is illuminated by string lights, creating a cozy atmosphere. A round table with several chairs is placed on a wooden deck, surrounded by neatly trimmed greenery. The two-story building is visible in the background, enhancing the inviting outdoor space.

Condo in Bridgeport

The Oasis / Free street parking

Enjoy this quiet home base with easy access to downtown! Recently rehabbed 1st floor unit. Free easy street parking, chef's kitchen, lush backyard. On a quiet street, walk to parks, coffee shops, grocery store, restaurants, Ramova Theater, Bridgeport Art Center, White Sox. Near red & orange line trains. Quick train ride to downtown. Quick drive to Midway Airport & McCormick Center. No dishwasher Free washer dryer No chores at checkout =) Free early check in/late checkout *if available*

An elegant event space is displayed with high ceilings and exposed brick walls. Rows of wooden chairs are set on a paved path leading toward soft lighting and greenery. Lanterns are positioned on the ground amidst floral arrangements, creating a welcoming and serene atmosphere.

4.9 out of 5 average rating, 31 reviews

Cozy Apartment in Bridgeport

Welcome to our newly remodeled apartment located in the historic Bridgeport neighborhood! This 2-bedroom unit is located on the basement of a two-flat building providing a clean and comfortable living space for families and groups to Windy City. Minutes to Downtown, McCormick Place, Guaranteed Rate Field, Chinatown, etc. Walking distance to Bridgeport Art Center, Zhou B Art Center, Maria Community Bar, Bridgeport Coffee, Wilson Park, Bridgeport Village river walk, many restaurants.

Guest suite in McKinley Park

A spacious backyard features a wooden deck with a pink picnic table and two blue chairs. Flower beds and a fire pit are visible among the greenery. A grill and a small stone area are also included, surrounded by a privacy fence.

4.9 out of 5 average rating, 110 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.

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, 29 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.

An ornate entrance gate welcomes visitors with the phrase 'Bienvenidos a Pilsen,' crafted in bold lettering. The intricate ironwork frames the entrance, reflecting the vibrant character of the Pilsen neighborhood. Light filters through the transparent doors, hinting at the lively atmosphere beyond.

4.87 out of 5 average rating, 264 reviews

Spectacular Pilsen Studio for 2!

This chic studio in the heart of Pilsen is the perfect space to kick back and relax during your visit to the Windy City! The vibrant neighborhood always has something to offer to any type of traveler, and it's a quick trip to see most of the iconic Chicago sights. Easily walk to historic Thalia Hall, or drive to the Loop in just 5 minutes! You'll love the thoughtful touches and modern decor in the apartment, as well as the bright and welcoming main space.

4.99 out of 5 average rating, 231 reviews

A modern living area features a green velvet couch and a round wooden coffee table atop a patterned area rug. A television is positioned on a media console, with natural light coming through multiple windows. Artwork adorns the walls, adding character to the space.

Apartment in Chicago

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.

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Popular amenities for Bridgeport, Chicago vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Bridgeport, Chicago's top sights

National Museum of Mexican Art28 locals recommend

Guaranteed Rate Field44 locals recommend

Chinatown89 locals recommend

Other great vacation rentals in Bridgeport, Chicago

A modern kitchen displays sleek white cabinetry and stainless steel appliances. A gas stove is paired with a microwave above, while a dining table with four light-colored chairs occupies the space. Natural light enters through a window, enhancing the open-concept design.

4.84 out of 5 average rating, 44 reviews

Cozy Home w/ Gorgeous Natural Light | Sox Stadium!

DarinRating, 5 stars1 week ago

Justin was great and always very responsive. very patient even when we didn't fully read the instructions about check in procedure. had one issue with the water pressure in the shower and he was willing to get someone out same day to address which we declined. place is very clean and parking can be challenging, but over all great experience and great host. a long walk but walkable to Chinatown and other locations. Would be a great place for a Sox game or Chinatown. neighbors are nice and respectful and the bakery about 2 blocks down is fantastic. would definitely recommend. Older building and not much from the outside but inside very clean and well maintained. Great communication and host.

A hallway showcases an arched entryway leading into a shared living space. Light grey walls provide a soft backdrop for the hardwood flooring. A white door stands ajar, revealing additional areas such as the dining table and kitchen, enhancing a sense of openness.

Private room in Chicago

4.72 out of 5 average rating, 39 reviews

Bees Knees - Room 3

MikaylahRating, 5 stars3 weeks ago

I really enjoyed my stay here . Genova place is very affordable, well kept for a shared space . I like that everything was organized . Toiletries such as body soap , hair conditioner was provided as well as towels and linens . Genova was able to accommodate me as well with some plans that didn’t quite work out with my airfare . I was very grateful and appreciative of that as well . Very good and timely with communication on whatever I needed . I’m sure a future stay here will be planned out . Maybe sooner than later . Great host . Until next time …

Superhost

A comfortable seating area features a black sofa positioned in front of a wooden coffee table. Natural light enters through two windows, brightening the space. A stylish mirror reflects the surroundings, while a queen-sized bed is visible in the background, adorned with soft bedding.

Private room in Bridgeport

4.87 out of 5 average rating, 204 reviews

The Sweet!

ChrisRating, 5 stars1 week ago

This was the perfect place to stay for the first time visiting Chicago. Easy to find and in a great neighborhood. Hosts were extremely responsive and helpful. Highly recommend and would stay again!

A stylish living area features a light grey sectional sofa with an orange throw blanket. Large windows are dressed with sheer curtains, allowing natural light to brighten the space. Art prints in simple frames adorn the wall, while a potted plant adds a touch of greenery.

4.89 out of 5 average rating, 9 reviews

Windy City Escape- 2 queen BR

DerekRating, 5 stars1 week ago

The place was super clean and newly remodeled. The neighborhood was quiet at night. We stayed for an event at Northerly Island which was only about a 12min uber. Would stay here again.

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, 12 reviews

Urban Penthouse- Lux Rain Shower, Church View

TravonneRating, 5 stars4 weeks ago

This was an amazing place to stay at! The host Thomas was a good host and was always responsive whenever a situation occurred or a heads-up on something. The place was great and amazing especially the bathroom was comforting to say. Overall the experience there was fantastic especially the places to go to eat or travel around. Would love to book again!!

A wooden bench with a cross-back design is positioned in a landscaped yard. Lush greenery and shrubs are visible in the background, along with a paved pathway. The area is well-maintained, providing a serene outdoor space for relaxation.

4.64 out of 5 average rating, 117 reviews

Entire 1-Bedroom Apt by Chinatown

Dr. NatashaRating, 5 stars4 weeks ago

Felt right at home and would definitely stay here again. Check-in was easy and she was kind enough to wait to greet us. Weihong's apartment looks even better in person than it does in the photos. The apartment was spotless and she allowed us to check-in early. There was ample street parking when we arrived on Saturday and we didn't have move the car until we returned home. Walking distance to the orange line and Chinatown.