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Vacation rentals with a patio in South Side

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Top-rated accommodations with an outdoor patio in South Side

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Guest suite in Chicago

Comfortable and Cozy Suite in Quiet Neighborhood

Are you coming to town to visit family, friends or for business? This cozy, clean, comfortable & 420 friendly suite has all you need to escape your everyday. Look no further! This one-bedroom suite is perfect for 1-3 people, small families, or individuals. If you're visiting family or friends and want your personal space or are in town for business and need a comfy bed, wifi, and office space, then this place was designed for you. Kick back and relax in this calm, stylish, 420 friendly space.

Rental unit in Chicago

Eclipse: Apt. in Woodlawn | Near UChicago

Modern 2 bedroom basement apartment has a style of its own and is perfect for your stay in Chicago. It's a central location to explore Chicago w/ vehicle, ideal for working professionals & families visiting students and medical hospital. Driving: Located 6 min to University of Chicago, mins to lakefront and beach. 10 min to Hyde Park restaurants and attractions, 20 min downtown Chicago. Near expressways. Code entry for convenient check-in and free street parking. Please read entire listing!

Guest favourite

Home in Chicago

Spacius unit in historic gem

Bring the whole family to this great place with lots of room for fun. Two retro arcade games & an air hockey table to enjoy. Spacius apartment with room for everyone to relax comfortably. Super close to everything Chicago has to offer. 12 minutes to the heart of downtown. 5 minutes to the University of Chicago. 8 minutes to McCormick place, Soldier Field, Credit 1 Arena and Sox Stadium 10 mins to the beach/lake 15 mins to the United Center Walking distance to 2 train lines leading downtown

Guest favourite

Rental unit in Cicero

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

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

Guest favourite

Rental unit in Oak Park

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!

Guest favourite

Home in Chicago

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Guest favourite

Condo in Chicago

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.

Guest favourite

Rental unit in Chicago

Chic & Cozy, New Build 2beds, 15mins from The Bean

Enjoy an Art Deco experience at this centrally-located place, in the heart of historic Bronzeville, Chicago. This 2 bedroom with 2 queen beds unit is the perfect base for your Windy City adventures. With modern amenities, comfortable furnishings, and a prime location in one of Chicago's most historic neighborhoods, you'll feel right at home in this cozy and stylish retreat. 15 minutes away from downtown, 5 minutes away from Lake Michigan, amazing eateries, park and the interstate I90-94

Guest favourite

Rental unit in Forest Park

Home in Forest Park upstairs.

In this cozy apartment you will have a small but functional kitchen, in unit laundry, fast WiFi connection and access to a back yard.. It’s an old building but conveniently located 30 minutes from O'Hara International Airport, 20 minutes from Downtown Chicago via I-290, and 40 minutes away from Midway Airport. Forest Park is a very safe, vibrant and diverse suburb of Chicago. You will be within walking distance of many different restaurants, boutiques, bars, parks, and public transit

Guest favourite

Rental unit in Berwyn

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.

Guest favourite

Guest suite in Chicago

The Landmark; a comfy suite near McCormick Place

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.

Guest favourite

Guest suite in Chicago

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.

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Popular amenities for South Side accommodations with an outdoor patio

Free parking on premises

Air conditioning

Apartment rentals with a patio

Guest favourite

Rental unit in Chicago

Historic Old Town Flat - Minutes from Downtown!

Guest favourite

Rental unit in Chicago

Cozy Lincoln Park Studio - Steps to Zoo!

Guest favourite

Rental unit in Palatine

Huge Sofa-Private Deck-King Bed-Downtown-Retro Apt

Guest favourite

Rental unit in Chicago

Lincoln Pk-Kingbd-fast WiFi-parking-crib/Highchair

Rental unit in Chicago

Logan Square Beauty with 2 Bedrooms W/parking

Rental unit in Chicago

Luxurious 3 Bedroom Getaway

Rental unit in Chicago

Cozy 2 bdrm w/ patio mins from Midway Airport

Rental unit in Chicago

McCormick 2B/2Ba for up to 6 guests/private Patio

House rentals with an outdoor patio

Guest favourite

Home in Chicago

Division St Designer Home In Heart of Wicker Park

Home in Bolingbrook

The Sunshine Spot

Guest favourite

Home in Chicago Ridge

Quiet cul-de-sac with huge fenced in backyard

Guest favourite

Home in Chicago

Modern Family Townhouse

Guest favourite

Home in Chicago

Modern Historic Greystone - Near Lake - Free Prkg

Guest favourite

Home in Chicago

Chicago Home by Midway near Downtown Attractions

Guest favourite

Home in Chicago

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

Guest favourite

Home in Chicago

NEW! Lake & Skyline View on Kenwood Culdesac!

Condo rentals with a patio

Guest favourite

Condo in Chicago

Spacious 4 Bedroom Condo

Guest favourite

Condo in Chicago

Updated Designer Duplex In Fulton Market W/parking

Guest favourite

Condo in Chicago

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Guest favourite

Condo in Chicago

Interior designer duplex 2bd 2bath w/ prvt backyd

Guest favourite

Condo in Chicago

Lincoln Park 2bed/2bath in Historic Neighborhood

Condo in Chicago

Tri-Taylor/Medical Dist. near West Loop

Guest favourite

Condo in Chicago

The Grand Kimball Lodge, Logan Square, Sleeps 14

Condo in Chicago

Can't Beat This 2min Walk to Wrigley!

Destinations to explore