Vacation rentals with a patio in Bridgeport, Chicago

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Top-rated patio rentals in Bridgeport, Chicago

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Guest favorite

Apartment in Chicago

4.98 out of 5 average rating, 57 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

Jun 15 – 22

G$58,506 GYD per night

Guest favorite

Home in Chicago

4.93 out of 5 average rating, 71 reviews

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! If you have any questions, please ask before submitting request. Hot tub 5-6 Person Spa 45-Jet

Aug 15 – 22

G$72,640 GYD per night

Guest favorite

Apartment in Oak Park

4.91 out of 5 average rating, 104 reviews

Lovely, spacious 2bd, 1bath home w/free parking

Bring the whole family to enjoy this great place with lots of comforts and space. Beautifully decorated with reclaimed barn wood throughout the home and a completely remodeled kitchen with cute bistro table to enjoy your coffee. Wonder around this beautiful, quiet Frank Lloyd Wright neighborhood to see beautiful Victorian homes and architect or take a brisk walk to downtown Oak Park before taking in the sites in Downtown Chicago. Whether you stay for a while or a few days, welcome home!

Sep 29 – Oct 6

G$26,152 GYD per night

Guest favorite

Condo in Chicago

4.92 out of 5 average rating, 77 reviews

Convenient & Spacious 3BR Condo w/Free Parking

Get cozy in this spacious 3-bedroom condo, conveniently located 3 blocks from the Halsted Orange Line overlooking Palmisano Park and only 5 minutes' drive to McCormick Place. Clean, neat, modern and comfortable, the condo offers spacious living space with an open kitchen, washer/dryer, and an outdoor balcony perfect for families and groups. Hungry? Our complex offers a few delicious high rated yelp restaurant options to fulfill your appetite. We look forward to hosting you and your guests!

Sep 22 – 29

G$55,016 GYD per night

Guest favorite

Condo in Chicago

4.96 out of 5 average rating, 119 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Sep 19 – 26

G$74,157 GYD per night

Guest favorite

Apartment in Berwyn

4.87 out of 5 average rating, 137 reviews

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

Jul 19 – 26

G$21,950 GYD per night

Guest favorite

Guest suite in Chicago

5.0 out of 5 average rating, 14 reviews

The Landmark; a comfortable suite in the Gap

Welcome to the landmark. A cozy well appointed studio space in the heart of the historic Calumet/Giles Prairie district. Bright, east-facing, ground floor unit with 9 ft ceilings and separate entry. We have everything you’ll need for a comfortable leisure getaway or business trip. Conveniently situated near IIT, McCormick Place, Sox Field, Wintrust Arena, three major highways, and downtown. Walk to 31st street beach or bike the lake to Museum Campus. It’s all at your fingertips.

Jul 25 – Aug 1

G$47,842 GYD per night

Guest favorite

Guest suite in McKinley Park

4.9 out of 5 average rating, 73 reviews

1 bed apartment + futon room bridgeport

Located at the geographic center of Chicago! Plenty of free street parking. Very safe and ~10 min walk to the 35th Orange line and 3 blocks from the Archer bus, both go directly downtown within minutes. Brand new lower level construction unit. Comfortable spacious rooms to relax in. Closet in both rooms for your use while here. The apartment has a separate entrance, bathroom, kitchen, dining space. Enjoy your own private space in Chicago with a back patio, grill, and laundry.

Jun 19 – 26

G$25,351 GYD per night

Guest favorite

Home in Chicago

4.91 out of 5 average rating, 44 reviews

Cozy Bright Quiet Boho-Chic House in Bridgeport

Kick back & relax in your home away from home in our modern, quaint, cozy & peaceful space in the heart of the Bridgeport neighborhood. Featuring incredible natural light, modern amenities & playful artwork, the coach house is impeccably clean and designed to ensure you have the best travel experience possible. Located near the popular Halsted Street, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Apr 27 – May 4

G$26,611 GYD per night

Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 6 reviews

Casita Plzeň First Floor

Built in the 1850s, and restored to its original Chicago Worker's cottage greatness in 2022. The Airbnb is located in the center of the Pilsen neighborhood, and on a quiet tree-lined street. It is a spacious 2 bedroom apartment, located steps away from the 18th St. El Station, (4 stops to Loop) cafes, breweries, art galleries, murals, vintage/plant shops, and eclectic food options, from neighborhood hero Bob's pizza, to Netflix renowned Rubi's Tacos.

Sep 8 – 15

G$34,427 GYD per night

Guest favorite

Apartment in Cicero

4.98 out of 5 average rating, 202 reviews

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

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

Jan 1 – 8

G$26,084 GYD per night

Guest favorite

Home in Chicago

4.97 out of 5 average rating, 38 reviews

Spacious Luxury Retreat 8 Bed Oasis with 6 Baths

Welcome to our spacious and luxurious retreat in the vibrant city of Chicago! This magnificent single-family home boasts 6 beautifully appointed bedrooms and 5.5 modern bathrooms, providing ample space for large groups or families seeking the ultimate comfort and convenience. Step inside and be greeted by an atmosphere of elegance and refinement. The open and airy layout of this home offers plenty of room to relax and unwind.

Dec 16 – 23

G$184,490 GYD per night