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Smoking friendly vacation rentals in North Side

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Vacation rentals for every style

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Popular amenities for North Side smoking friendly rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Smoking friendly apartment rentals

Superhost
A vibrant green wall features an assortment of decorative mirrors and picture frames in varied shapes. A sleek yellow console table is positioned beneath, adorned with a decorative object and a potted plant. A transparent chair complements the modern aesthetic.
Apartment in Calumet City
4.76 out of 5 average rating, 29 reviews

The Green Lantern

A charming house stands amid a lush garden, featuring a variety of plants and shrubbery. Straw and natural materials create beds for growing vegetables. Sunlight filters through the trees, illuminating the scene, while the structure showcases a welcoming porch and a pitched roof.
Apartment in Chicago
4.84 out of 5 average rating, 133 reviews

Studio Apartment in Nature Sancturary

Guest favorite
A spacious living area features a sectional sofa with patterned cushions, a coffee table adorned with magazines, and a foosball table nearby. The kitchen space is visible, showcasing modern appliances and stylish cabinets, while a feature wall adds a unique touch to the room.
Apartment in Chicago
4.79 out of 5 average rating, 33 reviews

Hype Loft Experience

A well-lit kitchen area features wooden cabinetry, a gas stove, and a sleek countertop. A small plant sits on the counter, while a clock is mounted above the stove. Natural light streams through a nearby window, illuminating the inviting space.
Apartment in Franklin Park
4.55 out of 5 average rating, 11 reviews

Cozy Apartment in Franklin Park

A spacious living area is showcased with a comfortable couch and a flat-screen television positioned on a media console. Light wood flooring leads to an adjacent dining area with a set of chairs and a table, enhancing the open layout.
Apartment in Chicago
4.67 out of 5 average rating, 3 reviews

Smokers Preferred 420 friendly

A modern kitchen layout is presented, featuring sleek cabinetry and stainless appliances. An island with seating is visible alongside a dining table for four. Soft overhead lighting highlights the space, while a small plant adds a touch of greenery. The walls are painted in a calming light color.
Apartment in Chicago
4.52 out of 5 average rating, 33 reviews

La Villita - Gateway to Chicago

Superhost
An outdoor lounge area features a rectangular table with a central firepit, surrounded by comfortable seating with purple cushions. The backdrop showcases the Chicago skyline against a clear blue sky, adding a scenic view to this rooftop retreat.
Apartment in Chicago
4.83 out of 5 average rating, 54 reviews

Rooftop HotTub As Seen On "Married At First Sight"

A bright living area features a blue sectional sofa oriented towards a wall-mounted television displaying the Netflix logo. A glass coffee table is positioned in front of the sofa, with a decorative candle resting on it. Two large windows provide natural light.
Apartment in Chicago
4.77 out of 5 average rating, 141 reviews

Stylish 1BR South Loop Near McCormick & Wintrust

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Smoking friendly house rentals

An outdoor patio area features a long wooden table surrounded by eight light-toned chairs. Potted plants add greenery, and a bar area with stools can be seen in the background. A blue umbrella provides shade, enhancing the inviting setting.
Home in Berwyn

Music Hot Spot Three Level Home

A stone fireplace serves as the focal point of the cozy living space, with flames gently flickering. Soft seating is arranged around a simple wooden coffee table, complemented by a patterned chair. A dimly lit lamp casts a warm glow, enhancing the inviting atmosphere.
Home in Lemont
4.65 out of 5 average rating, 62 reviews

Nature retreat hide n seek private suite/ house

A contemporary house is illuminated at night, featuring large glass walls that reflect colorful lights from within. The structure is surrounded by trees, and a circular driveway is visible with a parked vehicle nearby, creating a private and secluded ambiance.
Private room in Lake Zurich
5 out of 5 average rating, 4 reviews

Private Room in Large Home with Basement Gym

A welcoming entrance to the property is depicted, featuring a brick facade and large windows. A round lamp post stands at the front, casting a soft glow, while the front door is framed by a small step leading up from the sidewalk.
Private room in Chicago
4.5 out of 5 average rating, 8 reviews

Room3

Superhost
A spacious living room showcases stylish wooden accents, featuring a glass coffee table on a decorative rug. A comfortable recliner and various entertainment units are visible, while a doorway leads to another area of the home, creating an inviting and open atmosphere.
Private room in Chicago
4.87 out of 5 average rating, 100 reviews

A Cozy Room for Two in Vibrant Logan Square

Superhost
A spacious living area features a modern television mounted on a light-colored wall, flanked by a comfortable sofa set. A neutral coffee table sits centrally, while soft natural light enhances the inviting atmosphere through large windows. A dining area is visible in the background.
Home in Romeoville
4.92 out of 5 average rating, 13 reviews

Rejuvenate: 4BR, fenced yard

A comfortable living area features a grey sectional sofa, accented with patterned cushions. A dark wooden coffee table is center stage, resting on a light area rug. A flat-screen television is mounted on the wall, with natural light illuminating the space through nearby windows.
Private room in Chicago

The Estate-Private bedroom

A stylish living area features a large flat-screen TV mounted on the wall, above a sleek media console. A modern mirrored coffee table complements the space, and a bouquet of red roses adds a touch of colour against the neutral backdrop of grey curtains.
Home in Calumet City
4.8 out of 5 average rating, 10 reviews

Cozy Retreat in Calumet City

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Smoking friendly condo rentals

Guest favorite
A spacious living area features a modern sectional sofa in warm tones, positioned around a circular coffee table. Large windows allow natural light to fill the room, showcasing a view of the outdoors. A neutral area rug anchors the seating arrangement, enhancing the home’s contemporary design.
Private room in Chicago
4.88 out of 5 average rating, 305 reviews

Private BR in Condo close to Chicago Dwtwn!

A sprawling cityscape is captured at twilight, with tall skyscrapers illuminated against a purple sky. Reflections of the buildings shimmer on the river below, while lights from windows create a vibrant urban atmosphere. The scene captures the dynamic essence of city life.
Condo in Chicago
4.45 out of 5 average rating, 11 reviews

voco: Balcony & City View

A well-lit hallway features smooth wooden flooring and a neutral area rug. Framed art pieces adorn the walls, while a stylish console table holds decorative items. Potted plants and a modern chair create a welcoming atmosphere at the far end of the corridor.
Condo in Chicago
4.5 out of 5 average rating, 10 reviews

Urban Oasis: South Shore Chicago

Top guest favorite
Condo in Chicago
5 out of 5 average rating, 59 reviews

Where you want to BE! Stylish, Comfy, Luxe

Guest favorite
A modern kitchen showcases stainless steel appliances and elegant cabinetry. A large island is accentuated by unique stools, while pendant lighting adds soft illumination. The open floor plan leads to a welcoming living area visible in the background, enhancing the spacious design.
Private room in Chicago
4.8 out of 5 average rating, 92 reviews

Master BR w/ensuite (600 Sq Ft.) in Chicago Condo

Top guest favorite
A long hallway is lined with chalkboard-painted walls, showcasing colorful drawings and notes. Light is provided by ceiling fans and bright fixtures, leading towards an entryway with a glimpse of furniture and natural light coming from an open door.
Private room in Chicago
4.87 out of 5 average rating, 83 reviews

Beautiful condo close to the beach

Guest favorite
A spacious living area features a leather sectional couch arranged around a round coffee table. Large windows allow natural light to fill the room, highlighting the hardwood floors and elegant chandeliers above. A plush area rug contrasts with the dark wood, creating a cozy atmosphere.
Private room in Chicago
4.89 out of 5 average rating, 268 reviews

Private BR in Chicago - Dwntwn & Fulton Mkt close

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