Holiday houses in Bridgeport, Chicago

4.96 out of 5 average rating, 123 reviews

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

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

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

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

5 out of 5 average rating, 76 reviews

Condo in Bridgeport

The Oasis / Free street parking

Nothing compares to summertime in Chicago! 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*

4.72 out of 5 average rating, 54 reviews

Home in Bridgeport

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.

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.

4.77 out of 5 average rating, 108 reviews

1B-by China town/White Sox/McCormick/S.Loop/City

“Cozy 1-Bedroom Apartment – Free Parking, Near McCormick Place” Relax in this quiet, cozy one-bedroom apartment, just minutes from Chicago’s top attractions. The apartment includes two living areas, a fully equipped kitchen, and a compact bathroom with a tub.The unit it self on a second floor. •7-minute drive or 30-minute walk to McCormick Place. •Free street parking available right outside Perfect for a peaceful stay with easy access to all the excitement Chicago offers.

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.

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, 232 reviews

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.

4.97 out of 5 average rating, 213 reviews

Home in Bridgeport

Peaceful Modern Full House in Trendy Bridgeport

Kick back & relax in your home away from home in our modern & peaceful space in the heart of the Bridgeport neighborhood. Featuring incredible natural light, modern amenities & beautiful artwork, 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.

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Popular amenities for Bridgeport, Chicago holiday rentals

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Stay near Bridgeport, Chicago's top sights

National Museum of Mexican Art28 locals recommend

Guaranteed Rate Field44 locals recommend

Chinatown89 locals recommend

Other great holiday rentals in Bridgeport, Chicago

Private room in West Lawn

4.85 out of 5 average rating, 391 reviews

The Red Room

JakeRating, 5 stars3 weeks ago

Erik was a phenomenal host, went above and beyond to ensure we had a comfortable stay at his house. His family were lovely people and helpful with any and all questions. Erik gave is good clear instructions on the best places to go to in the area, how to travel to the city and how to use all the appliances/facilities in the house. I couldn’t recommend him any more, he made our stay really more comforting and laid a great basis for our stay in Chicago. Cheers Erik!

4.84 out of 5 average rating, 45 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.

Apartment in South Side

5 out of 5 average rating, 3 reviews

Sunny Penthouse - Oakwood Beach

DeannaRating, 5 stars3 days ago

Manny and Veronica have a beautiful apartment and were amazing hosts! They helped with any issues and were more than accommodating of me and the 3 other guests I booked with! Communication was quick and if I needed anything, they were more than ready to assist. The apartment is really spacious, supurb natural lighting, great appliances, and is decorated in such a way that it feels very homey. It's a 5 minute drive from a great grocery store and restaurants are not that far in a very comfortable and safe feeling area. It was a great place to come back to after spending the day out and about, I highly recommended staying here if you want a super nice and comfortable Chicago stay!

4.85 out of 5 average rating, 184 reviews

Private room in Pilsen

BOHEMIAN LODGE #2 (clean & affordable travel)

DantonRating, 5 starstoday

Great place! Amazing for those traveling on a budget, especially those who are ok with others in the same building (You get a private room AND your own bathroom connected directly to your room)

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!

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.