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Smoking friendly vacation rentals in North Side

Find and book unique smoking friendly rentals on Airbnb

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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

Apartment in Chicago
4.76 out of 5 average rating, 67 reviews

Modern 3BR 420-OK Near Convention Center

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, 134 reviews

Studio Apartment in Nature Sancturary

A cozy sleeping area is featured, showcasing a spacious bed dressed in a light-colored quilt. A window above allows natural light to filter in, enhancing the serene atmosphere. Potted plants and artwork adorn the space, providing a touch of warmth.
Apartment in Downers Grove
4.74 out of 5 average rating, 85 reviews

Pet friendly private studio apartment in a home

A spacious living area features a plush sectional sofa adorned with decorative pillows. A tasteful coffee table rests on a patterned rug, while a well-equipped kitchen is visible in the background, complemented by sleek cabinetry and modern appliances.
Apartment in Chicago
4.78 out of 5 average rating, 36 reviews

Hypebeast Experience

Guest favorite
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
4.83 out of 5 average rating, 6 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

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
4.82 out of 5 average rating, 57 reviews

Private Penthouse, Stunning Rooftop Views!

Top guest favorite
A billiards table is positioned in a well-lit area, with a mounted television visible on the wall. Two cues and a set of colorful pool balls are arranged on the table. Wooden cabinetry can be seen in the background, complementing the modern decor.
Apartment in Chicago
5 out of 5 average rating, 6 reviews

Loft Style Wicker Park Apartment

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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

An above-ground pool is surrounded by a wooden deck, featuring colorful inflatable pool toys. A shaded dining area with a blue umbrella is adjacent, while lush greenery creates a natural backdrop, providing a sense of privacy and relaxation.
Home in Lemont
4.55 out of 5 average rating, 67 reviews

Nature retreat hide n seek private suite/ house

Guest favorite
A comfortable bedroom features a spacious bed with white linens, accented by two decorative pillows. Natural light fills the room through two windows with bamboo shades. A small bedside table and a dresser contribute to the room's functional layout, complemented by a ceiling fan for airflow.
Private room in Rolling Meadows
5 out of 5 average rating, 5 reviews

Master bedroom suite with attached bathroom

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

Guest favorite
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, 101 reviews

A Cozy Room for Two in Vibrant Logan Square

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

Guest favorite
A brick house with a distinctive architectural style is set behind a black metal fence. The front yard features green grass and is bordered by a sidewalk leading to the entryway. Large windows allow natural light to enter the home, enhancing its welcoming appearance.
Home in Chicago
5 out of 5 average rating, 10 reviews

Chicago's Finest Airbnb/airport shuttle/ tours.

A spacious entryway features a wooden dining table at the center, complemented by a black rug. Natural light enters through large windows, illuminating the polished hardwood floor. A cozy seating area is positioned to one side, and a staircase is visible leading to upper levels.
Home in Chicago
New place to stay

Artsy 3Bdr Getaway-Walking distance to the Lake!

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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
4.89 out of 5 average rating, 319 reviews

Private BR in Condo close to Chicago Dwtwn!

A serene bedroom is illuminated by soft purple lighting. A spacious bed with a polka dot blanket is centered in the room. Floor-to-ceiling glass doors reveal a view of a vibrant city skyline at night, with city lights twinkling in the background.
Condo in Chicago
4.35 out of 5 average rating, 23 reviews

voco: Balcony & City View

A spacious living area features a large sectional sofa draped with a cozy throw. Soft lighting is provided by recessed ceiling lights. A stylish desk and chair are positioned nearby, complementing a picturesque wall-mounted television that serves as a focal point in the room.
Condo in Chicago
4.44 out of 5 average rating, 25 reviews

Urban Oasis: South Shore Chicago

Top guest favorite
A well-lit hallway is adorned with framed artwork and a stylish console table. At the end of the hallway, a cozy seating area with a round dining table and four chairs is visible, illuminated by natural light from large windows.
Condo in Chicago
5 out of 5 average rating, 60 reviews

Where you want to BE! Stylish, Comfy, Luxe

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, 282 reviews

Private BR in Chicago - Dwntwn & Fulton Mkt close

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