
Apartment holiday rentals in Bridgeport
Find and book unique apartments on Airbnb
Top-rated apartment rentals in Bridgeport
Guests agree: these apartments are highly rated for location, cleanliness and more.

Walk to UC, No Stairs, Free Parking
Modern 2BR/2BA with chefâs kitchen, King suite with private bath, Easy no-stairs access, park next to the unit and walk in within steps + dedicated garage parking, level 1 - EV charging, rooftop city views. Easy access: - Private street-level entrance, no stairs. - Park right next to the unit and be inside within steps. - Ideal for seniors, guests with disabilities, and families with strollers. - Near the United Center - 10 min to McCormick Place - 12 min Downtown Chicago - Sleeps up to 8

Prime Bridgeport â 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

Unmatched Urban Retreat Close to 18th Strip & Loop
This stylish Airbnb in the very popular Pilsen neighborhood is perfect for small and large travel groups. There are 2 bedrooms with queen size beds, and the couch folds out for an additional sleeping area. The 2 full bathrooms will have everything you need to get ready to hit the town. The tall ceilings make this space for larger than life, and the unique dĂŠcor gives this Airbnb a great urban feel. The fully equipped kitchen and updated appliances are perfect for those quiet nights in.

A Quiet Stay While You Are Away Oak Park
Welcome to our cozy and comfortable home located in a quiet neighborhood. Our space is perfect for couples, solo travelers, small families, and long-term stays. This is a beautiful, modernist home located in the Frank Lloyd Wright District Neighborhood, a designated historic district known for its collection of homes designed by the famous architect Frank Lloyd Wright. This district features a collection of some of his iconic designs and is a destination for architecture enthusiasts.

WF Home Sweet Home
Located in the center of the Bridgeport area, This AirBnB is clean, tidy, cozy and comfortable. It's the first choice for visitors. Two minutes walk to 8 and 31 bus stop, 15 minutes drive to downtown, McComick Place, and it close to Chinatown and White Sox Field. In addition, you can enjoy a variety of cuisines in a few minutes' walk, including Chinese, Japanese, Korean, Mexican restaurant, Starbucks,McDonald's, Dunkin Donuts, CVS. Warmly welcome friends from all over the world

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 Chicagoâs 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.

Blue Brick Apartment in Bridgeport - Park for Free
⢠Free street parking ⢠Trains to Downtown!! ⢠Fully stocked kitchen ⢠Walk to dining & bars! ⢠Free parking pad in rear ⢠Noise monitoring equipment ⢠Walk score 93! Bike Score 92! ⢠600 sq ft apartment | 2nd floor | Patio ⢠Safe, working class neighborhood! ⢠Commute to Downtown: 15min (drive) ⢠28min (transit/train) | 22min(bike) ⢠Building video surveillance alarm system ⢠Washer | Dryer | Dishwasher are included ⢠Rideshare (Uber/Lyft) | Bikeshares(Divvy)

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.

Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
Kick back & relax in your home away from home in our artistic & peaceful space in the heart of the Bridgeport neighborhood. Featuring incredible natural light, modern amenities & beautiful decor, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located on popular Morgan Street, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Pilsen Modern Chic Retreat
Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

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 and many other local neighborhood gems.

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.
Popular amenities for Bridgeport apartment rentals
Weekly apartment rentals

Bright South Hyde Park Studio

Sunny Penthouse - Oakwood Beach

Bright & Spacious Boho Oasis: A Warm Retreat

Cozy Bridgeport Apartment

LIVN West Loop Chicago 2 Bedroom

Kasa | Spectacular City Views | Chicago

The Courtyard Escape

Modern unit in Bridgeport-Chicago
Private apartment rentals

Comfy Chinatown Townhome and 2 garage spots!

Charming 2-bdrm near Obama Library/Hyde Park

Grand Cozy Duplex: Chicago Haven

Fulton House #1 (2bd/ 1ba)

Lake Meadows Chic 1BR Getaway

Cozy Condo in Chicago Chinatown

La Casita Norte

Stylish Industrial 2BR 2 Bath Parking + EV Charger
Apartment rentals with a hot tub

Top Floor Views + Central Comfort

Super Paradise+65 Amenities*Downtown 15 Min

Skyline Oasis: City & Lake Views

Modern 4BR West Town Duplex | Best for LongStays

Belmont Pleasures - hot tub / arcade gaming room

420 friendly apt with 2 queens,1 full,1 twin bed

Checkerboard Studio, Private Outdoor Hot Tub, Yard

South Loop Suite (Indoor Pool ⢠Fitness Center)
When is the best time to visit Bridgeport?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $107 SGD | $126 SGD | $154 SGD | $132 SGD | $144 SGD | $149 SGD | $156 SGD | $146 SGD | $130 SGD | $130 SGD | $121 SGD | $118 SGD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about flat rentals in Bridgeport

Total holiday rentals
Explore 70 holiday rentals in Bridgeport

Nightly prices starting at
Bridgeport holiday rentals start at $25Â SGD per night before taxes and fees

Verified guest reviews
Over 3,730 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
70 of Bridgeport holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Bridgeport rentals

4.8 Average rating
Bridgeport stays are highly rated by guests â averaging 4.8 out of 5!
Destinations to explore
- Pet-friendly rentals Bridgeport
- Rentals with a patio Bridgeport
- Family-friendly rentals Bridgeport
- Rentals with outdoor seating Bridgeport
- Rentals with a washing machine and dryer Bridgeport
- House rentals Bridgeport
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- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- Lincoln Park Zoo
- University of Chicago
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Washington Park Zoo
- Illinois Beach State Park
- Loyola University Chicago





