Apartment vacation rentals in Bridgeport, Chicago

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Top-rated apartment rentals in Bridgeport, Chicago

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Guest favorite

Rental unit in Bridgeport

4.92 out of 5 average rating, 101 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

Guest favorite

Rental unit in Chicago

4.91 out of 5 average rating, 102 reviews

Ground-Level Speakeasy: 1BR-1.5BA Near Everything!

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

Guest favorite

Rental unit in Cicero

4.98 out of 5 average rating, 270 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

Guest favorite

Rental unit in Chicago

4.96 out of 5 average rating, 125 reviews

Cute, Clean, Cozy Apartment in Pilsen

Updated, clean and private apartment in Chicago’s unique Pilsen neighborhood. Located on a quiet, tree-lined street with private entrance, it's the perfect spot to rest after a day of exploring this great neighborhood and city. The apartment has a full kitchen with everything needed to make your morning coffee or prepare a meal. Conveniently located to McCormick Place and many of the city's attractions, including West Loop, downtown, United Center, Grant / Union / Douglass Park and more!

Superhost

Rental unit in Chicago

4.81 out of 5 average rating, 193 reviews

Your brand new Chicago suite (unit 1F)

Come stay in the home of an artist. Enjoy this comfortable eclectic apartment that's filled with great work from local artist. Enjoy the book collection while you relax on the tufted chaise or cozy up to the couch and enjoy netflix. You get the entire apartment to yourself. It has everything you need for a comfortable stay. The neighborhood is very quiet with multiple nearby transportation options. Surrounding neighborhoods just 10 min away offer many restaurant & entertainment options.

Guest favorite

Rental unit in Bridgeport

4.96 out of 5 average rating, 111 reviews

The Photographers' Place

Tina and Kevin are your hosts for this Vintage cozy 600 sq. ft. apartment. 1st floor. Plenty of light. City living in established Bridgeport Neighborhood. Convenient location to McCormick Place (2miles), WinTrust Arena, Downtown, Chinatown, UIC, IIT, Soldier Field and Sox Park for baseball fans. Art, music, restaurant, brewery within walking or short bus ride. Grocery, Walgreens, CVS, Restaurants, Dunkin Donuts, Starbucks, 1 block away. We're only a phone call or text away.

Superhost

Rental unit in Pilsen Historic District

4.84 out of 5 average rating, 112 reviews

Pilsen Blue Door

Beautiful, spacious, and super cozy 3 bedroom apartment in the heart of Pilsen if your looking for that at home Chicagoan feeling this is the place for you. Newly remodeled apartment featuring a large dining room, brand new kitchen, and bathroom. Experience living in one of Chicago’s most colorful communities, rich in history and culture. Not only is this apartment less than 9 minutes from downtown Chicago, you are walking distance to some of the best restaurants in Pilsen.

Superhost

Rental unit in Pilsen Historic District

4.84 out of 5 average rating, 275 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond.

Guest favorite

Rental unit in Chicago

4.98 out of 5 average rating, 180 reviews

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.

Superhost

Rental unit in Pilsen Historic District

4.82 out of 5 average rating, 465 reviews

Eclectic Artist Designed Sanctuary Heart of Pilsen

Start the day with a soothing cup of tea or Nespresso on the front stoop in the morning sunshine. White hardwood floors combine with mismatched artwork, glossy houseplants, and a classic leather Chesterfield for restorative afternoon naps. This apartment is owned and designed by an artist/musician and a philosopher. It is solely used for AirBnb guests, so it will truly feel like your own space. Come stay to get away, relax, and be inspired!

Guest favorite

Rental unit in McKinley Park

4.86 out of 5 average rating, 294 reviews

Charming loft style suite

Original loft style 2nd floor apartment with private entrance. Thoughtfully furnished two bedrooms with a queen bed in each room. Plus a build in king size tatami in family room. A eat-in kitchen is convenient for basic warm up/cooking. There is a mini fridge, coffee maker and microwave. 10-20 Minutes drive to Loop, Museum Campus, Mc Cormick Place, Illinois Medical District, Soldier Field, White Sox& United Center.

Superhost

Rental unit in Chicago

4.85 out of 5 average rating, 201 reviews

The Cottage

Nice cozy and welcoming place. Easy access to public transportation. 10 to 15 minutes from downtown, museums, Sox and Bulls stadiums. Located in the colorful and lively neighborhood of Pilsen and close to Little Italy. Smart devices installed for easy check-in and safety (extremely accurate and sensitive smoke detector warning all occupants of possible problems). Guest wifi included with some feel home amenities.