Vacation rentals in Bridgeport

Polk Street Coach House Apartment, Little Italy/Medical Dist

Cook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs. Welcome to Polk Street Guest House: a well-appointed, completely private, 2-bedroom carriage house in Little Italy near the Medical District. Decorated with mid-century antiques and paintings, our 2nd floor coach house apartment is perfect for guests looking for a home-away-from-home. It has a fully-equipped kitchen, teak furnishings, comfortable queen size beds, and a private entrance accessible though a side gate from the street. For folks with kids, please note there is no child gate near the top of the stairs. Enjoy quiet parks and have easy access to all of Chicago. Major hospitals at Rush, University of Illinois, Hines, VA and Stroger are within 3 to 6 blocks. Chicago's elevated pink line train is 2 blocks away; the Blue line is 3 blocks. Take a quick cab ride to “the loop" downtown for $10, or take a Divvy bike. Chicago's famed Little Italy restaurants on Taylor Street are a block South. Free street parking with 24-hour zoned pass. Your hosts: Ken & Curt Want privacy? You have privacy! Use an entry code to access the coach house through the side gate to the left of our main house. Your private entrance, which also has keypad entry, is on the left side of the vine-covered brick building in back. The main living area is upstairs. There will be a 24-hour zoned parking pass waiting for you on a shelf as you enter the Coach with instructions on how to fill out the parking pass. We regret that the Coach House is not ADA/wheelchair accessible. For those arriving early than check-in, or who are staying later than check-out, we have an area beneath the coach house where you may leave your luggage. Just ask. Our space is your space. The coach house is entirely separate from our main house where we live. The coach house has a separate entrance and full amenities. You’re welcome to use the seating area in the courtyard, and the Weber grill. We're happy to provide any tips about the city, or to help show you how to use anything in the apartment. Just call our cell phones (they are listed in the apartment), or step across the yard and say hello. Three blocks to the Medical District and major hospitals, walk from this tree-lined Little Italy neighborhood to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Indian cuisine on Taylor Street. Stroll in Garibaldi Park on the doorstep, with Arrigo Park a block away. We are conveniently located for transit, bike, car and Uber. Public Transportation: -Pink Line, Polk Station, CTA: 3 blocks west of us, this rail line gets you downtown in 10 minutes (plan 30 minutes total time with walking for most destinations) and is useful for most site-seeing. -Blue Line, Racine Station, CTA: 4 blocks east or west of us, this rail line gets you to O'Hare airport in less than an hour, or downtown in about 10 minutes (it's a bit longer walk to the Blue Line than to the Pink Line) . -#157 Bus (Streeterville): This super convenient bus 1 block south of us on Taylor Street runs during the daytime only and takes you to the Magnificent Mile for upscale shopping on North Michigan Avenue in 25 minutes. -#12 Bus (Roosevelt): This is about 3-4 blocks south of us, runs east-west, and takes you to the Soldier Field stadium and the Roosevelt Road shopping area with Whole Foods, Nordstrom Rack, Best Buy, Core Power Yoga, and much more. Bicycle: You bike? We bike. There is a DIVVY bike share station a block east in Arrigo Park. Get at DIVVY bike-share 24-hour pass with unlimited half-hour rides. Switch out bikes for longer distances. If you have your own bike, you can park it safely on the ground floor of your coach house apartment. It takes 15 to 20 minutes to bike to most downtown locations. Car: Our home is 3 blocks south of I-290 (the Eisenhower), and near I-55 (the Stevenson), I-90 and I-94 (the Dan Ryan and Kennedy). Parking: We provide parking passes for free zoned street parking available on a small shelf as you enter the Coach House along with instructions. Please be very careful about filling out the pass, as City workers seem motivated to issue tickets if the pass is not filled out correctly. We travel a lot and know what it's like to be away from home. That's why we've furnished the apartment with appealing furniture, comfortable beds, plenty of towels (and more towels), soaps, shampoos, and a kitchen outfitted with all the basics plus a few more: Kitchen Aid food processor, toaster, microwave, baking and cooking tools, Calphalon pots & pans. Please note there is no dishwasher. Enjoy complimentary Nespresso coffee, Bigelow teas, bottle water, and snacks. Three blocks to the Medical District. Walk the tree-lined streets of the Little Italy to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Asian cuisine on Taylor Street. Stroll in Garibaldi Park steps away, or Arrigo Park a block away.

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

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

Urban Cottage

For your Chicago trip, book at the Urban Cottage. You'll feel relaxed and worry-free in this tidy, well-stocked space. Blocks from cafes, restaurants, and bars, Ramova Theatre, White Sox stadium, and Marz Brewery. The South Loop and Museum Campus are less than 15 minutes by car, as well as Chinatown, McCormick Place, U of Chicago and more. Buses, trains, and bicycle rentals are within walking distance. Free street parking included. Have fun and relax in Chicago's leafy Bridgeport neighborhood.

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

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.

Sunny 1BR Walk-Up Bridgeport | Easy Street Parking

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.

The Oasis / Free street parking

Comfortable home in quiet, 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*

Bright & Cozy 2 Bedroom Apt - 15 Min to downtown!

Welcome to our cozy Chicago apartment located in the historic Bridgeport neighborhood! This 2-bedroom unit is located on the first floor of a two-flat building providing a comfortable and stylish retreat for travelers to Windy City. Located just steps away from a bus stop and a 5 min drive from the CTA Orange Line which provides easy access to the Loop, downtown sights, and all of Chicago's other neighborhoods. Adjacent to popular neighborhoods such as Pilsen and Chinatown.

Bridgeport Garden Studio

We completed a brand-new renovation of this basement apartment in 2024. It's compact, but modern and super clean! The building is a classic Chicago 3-flat, owner occupied , on a quiet street in the south-side Bridgeport neighborhood. Free washer and dryer in the rear utility room. Walking distance to Sox Park . 20 minutes by Uber to downtown Chicago. If you have a car, there is ample, free parking available on our street. One city block to the landmark Ramova Theater.

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.

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)