Vacation rentals in Bridgeport, Chicago

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Top-rated vacation rentals in Bridgeport, Chicago

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Guest favorite

An aerial view captures Guaranteed Rate Field bustling with fans on game day. The stadium is surrounded by a vast parking lot, with the Chicago skyline visible in the background, showcasing a mix of historic and modern buildings against a vibrant sunset.

Apartment in Bridgeport

4.94 out of 5 average rating, 148 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

Top guest favorite

A living space is captured, featuring a large television displaying vibrant underwater imagery. A coffee table reflects light and is positioned in front of a decorative fireplace. Natural wood elements and warm lighting create an inviting ambiance, leading toward a kitchen area in the background.

Condo in Bridgeport

5 out of 5 average rating, 30 reviews

Farmhouse of the Future (low clean fee, no chores)

Vintage maximalism meets hi-tech in this one-of-a-kind relaxing getaway. Far from trouble and noise but close to parks, summer fests, the loop, the White Sox, Obama library & more. Enjoy tall ceilings + rare amenities (heated bathroom floor, smart lights) and more suprises! No Costco shampoo or generic decor here. The eclectic and interactive design will stimulate kids and adults alike, and you may leave with inspiration for your own home. I am happy to customize the space to suit my guests :)

Top guest favorite

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.

Apartment in Bridgeport

5 out of 5 average rating, 12 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

The kitchen features wooden cabinets and a stainless steel stove. A microwave and various appliances are neatly arranged on the countertop. Subway tile backsplashes complement the granite surface, while a radiator and patterned area rug add character to the space.

Apartment in Bridgeport

5 out of 5 average rating, 23 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 favorite

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.

Apartment in Bridgeport

4.91 out of 5 average rating, 79 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

Top guest favorite

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

5 out of 5 average rating, 77 reviews

The Oasis / Free street parking

Nothing beats summer in Chicago! Enjoy this quiet home base with quick 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, 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*

Superhost

A bright living space features an orange sectional sofa and a patterned area rug. The walls are adorned with an eclectic mix of framed artwork and photographs. A coffee table with a stone finish sits center stage. Natural light filters in through the large windows.

Home in Bridgeport

4.71 out of 5 average rating, 56 reviews

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.

A countertop displays a Keurig coffee maker next to a kitchen sink. Below, a drawer reveals a neat arrangement of coffee K-pods in various flavors, alongside tea options and a small organizer for supplies. The countertop's surface is light-colored, complementing the stainless steel appliances.

Guesthouse in Bridgeport

4.91 out of 5 average rating, 350 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.

Guest favorite

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.

Apartment in Bridgeport

4.74 out of 5 average rating, 328 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.

An iconic reflective sculpture captures the city skyline at night, with numerous buildings illuminated and reflecting in its surface. A gathering of visitors can be seen around the sculpture, engaging with the vibrant urban environment.

Guest suite in McKinley Park

4.82 out of 5 average rating, 274 reviews

Vintage Suite Home Chicago by Sox/Park/Transit

Walkout basement studio in a ca.1890 home built for laborers in the Chicago Stockyards - Please read entire listing before booking. This quiet, tree-lined neighborhood is a respite from city buzz. Get downtown in 4 stops by train or any of 5 nearby buses. Your space has great natural light, 2 comfy beds (1 folds to couch), private bath, flexible work/dining area, super-fast WiFi, and kitchen with all the essentials. Private entry via back door Free street parking Se habla español

Superhost

A large fountain is showcased in the foreground, surrounded by water and illuminated by orange lights. The skyline of Chicago rises in the background, with several tall buildings and skyscrapers under a cloudy sky.

Apartment in Near South Side

4.78 out of 5 average rating, 147 reviews

McCormick Place Studio/parking/sleeps up to 4

• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security officers in the building • City view • Queen size bed + Queen size air mattress 2 extra guests • Comfortable stay for up to 4 guests at a time • Access to the Gym • Dedicated Internet • 4K smart HDTV(Netflix and Roku) • Fully equipped & stocked kitchen with complimentary Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day

Top guest favorite

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.

Apartment in Bridgeport

5 out of 5 average rating, 32 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.