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Smoking friendly vacation rentals in Cook County

Find and book unique smoking friendly rentals on Airbnb

Top-rated smoking friendly rentals in Cook County

Guests agree: these smoking friendly rentals are highly rated for location, cleanliness, and more.

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Apartment in Chicago

5 out of 5 average rating, 3 reviews

“Dream Catcher Suite” Gorgeous Multicultural Home

✨🦚✨ Welcome to The Dream Catcher Suite - private unit Thank you for selecting our place for your upcoming stay. We are excited to have you. Take a moment to see what's in store for you during your time on property: This is perfect for a family or a group of friends getaway! Enjoy our Gorgeous Multicultural Home and a nice 420 experience. FreeParking & own main door access code to check-in at ANY time after 3 p.m. no-hassle check-in guaranteed Safe & nice neighborhood with restaurants & stores

A pool table with a light brown felt surface is positioned in the foreground. In the background, a kitchenette with dark cabinetry and three wooden bar stools is visible. Two dark curtains frame the scene, enhancing the warm ambiance.

Condo in Chicago

4.72 out of 5 average rating, 36 reviews

Wicker Park Loft Style Apartment

Experience the best of Chicago with a stylish stay at our centrally-located home in the heart of Wicker Park! This space is packed with great amenities & just steps from the city’s top spots. Kick back & relax as you enjoy 1 of our three Smart TVs, play a round of pool, challenge each other to board games, or try your hand at darts. We’ve stocked the place with all the essentials. Feel at home & enjoy a complimentary welcome basket of snacks to start your stay off right. We cant wait to host you

An outdoor area features a partially enclosed space highlighted by warm wood paneling and a large window. A grill is positioned against the wall, with a concrete floor leading toward a well-lit interior visible through glass doors.

Home in Chicago

4.96 out of 5 average rating, 168 reviews

Chicago River House -Glowing Sofa Oasis

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

A well-lit hallway features dark hardwood flooring and white walls with an accent of dark paint. Doorways on either side lead to light-colored rooms, while a cozy seating area is visible at the end of the hallway.

Apartment in Chicago

4.95 out of 5 average rating, 105 reviews

420 at Cheltenham 4BR

If you want to experience an authentic piece of Chicago and it’s rich history, our place is a cozy spot to start and it’s just like being at home. Summertime Chicago Lake Shore Drive Beaches. Lollapalooza. Chicago Riverwalk. Concerts at Soldiers Field-Bears. Winter wonder festival. The Bean. Great for larger groups visiting looking to divide costs. Obama Library, Southshore golf course, Reggies on the Beach, Shedd Aquarium, Field Museum, Museum of Science & Industry are all within 20 minutes.

The kitchen features dark cabinetry and a sleek countertop, with a stovetop visible. Backlit artwork occupies one wall. Light wood flooring extends toward a spacious living area that includes a green sofa, while large windows allow natural light to fill the space.

Apartment in Calumet City

4.77 out of 5 average rating, 26 reviews

The Green Lantern

Relax and unwind with the family or friends at this peaceful place. A stylish 2 bedroom 1 bathroom home that has great work space with a warm inviting kitchen cozy bedrooms relaxing bathroom and unwinding living room. There is also great dining and entertainment nearby. The Green Lantern is located in the heart of everything, 25 minutes away from downtown Chicago, 30 minutes away from Joliet. Right next door to northwest Indiana. Come relax and enjoy this amazing home away from home…

An outdoor space is highlighted by a wooden deck featuring a picnic table and two blue chairs. A fire pit is visible on the grass, and string lights illuminate the area. Lush greenery climbs the walls, creating a welcoming atmosphere.

Guest suite in Chicago

4.89 out of 5 average rating, 102 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.

Top guest favorite

Home in Carol Stream

4.91 out of 5 average rating, 102 reviews

Lake House Hot Tub-Billiards-Kayak Waterfront Stay

Our beautiful home is the perfect place to gather with friends & family, relax, refresh, fish, have fun with your loved ones. It's the perfect home away from home with great views of the lake and on a quiet cul-de-sac. Stunning views of the lake while grilling or the firepit from the completely upgraded patio & the hot tub 🥂 🐶Up to 2 furry babies are allowed & they'll love the almost 1 acre fenced-in yard! (pet fee is extra & must be included at time of booking)

Guest suite in Chicago

4.94 out of 5 average rating, 157 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Private entrance apartment on the 2nd floor of this historic bungalow. Free street parking! Medicinal & recreational smokers permitted... outdoor ONLY. This comfortably cozy quiet get-away is nestled in NW Portage Park in a family neighborhood. Dog and kids park nearby. Fenced yard for Fido. Backyard patio w/ BBQ grill. High-speed internet. Front porch swing Easy access to buses & Jefferson Park Transit train station to Downtown & Museum Campus NO PARTIES

A modern kitchen features white cabinetry and a granite island with seating for three. Stainless steel appliances, including a refrigerator and stove, are visible. The tiled floor adds a clean touch, while natural light streams through a nearby window, illuminating the open layout to the living area.

Home in Romeoville

5 out of 5 average rating, 11 reviews

Rejuvenate: 4BR, fenced yard

Welcome to our cozy Romeoville retreat! This spacious one-level home offers plenty of room to relax and unwind. Enjoy cooking in the fully stocked kitchen, complete with all the essentials for your favorite meals. Step outside to the fully fenced backyard, perfect for outdoor dining, lounging, or letting kids and pets play safely. Whether you’re here for a weekend getaway or an extended stay, this home offers all the comfort and convenience you need.

A cozy outdoor deck features a round table with two folding chairs and a lounge chair. Overhead, stained glass windows allow filtered light to illuminate the space. Potted plants and decorative cushions add a touch of greenery and comfort, inviting relaxation.

Apartment in Chicago

4.95 out of 5 average rating, 693 reviews

Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

A red brick building is framed by lush greenery and features large windows. A black staircase leads to the entrance, which is accessible via a gentle slope. An adjacent chair stands on the concrete sidewalk, adding to the inviting exterior.

Guest suite in Chicago

4.91 out of 5 average rating, 110 reviews

The Huron Haven

A beautiful, one-of-a-kind, hidden gem in the heart of River West. Private entry. Front & Back Patios. Full office space. Large Living Room. Exposed brick walls, 11.5’ tall ceilings. Large barn doors lead from the living room / office to a large master bedroom with large modern bathroom. The bedroom has French doors which open to private balcony with a beautiful back patio, dining space, and thriving garden. On Property Parking

An open loft space features original wood floors and a cozy clawfoot tub near the living area. A long vintage dining table accompanies a mix of wooden and wicker chairs. Natural light floods the space through large windows, highlighting the room's unique architectural elements.

Loft in Chicago

4.82 out of 5 average rating, 247 reviews

Quirky Bucktown Loft w/ Parking No Parties

Located on a peaceful treelined street in energetic, fashionable Bucktown with upscale amenities at your fingertips. This unique penthouse/loft apartment has its share of quirks that come with being a 125-year-old building yet its unique vintage comfort, eclectic furnishings and modern necessities come together to make your time in the city relaxing and unforgettable. This is a legally licensed Chicago vacation rental R22000079930

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Popular amenities for Cook County smoking friendly rentals

Free parking on premises

Air conditioning

Smoking friendly apartment rentals

An outdoor deck area is presented, featuring a table surrounded by four blue chairs. Lush greenery creates a natural border, enhancing the space. An outdoor rug adds texture beneath the seating arrangement, while a staircase is visible in the background.

Apartment in Chicago

5 out of 5 average rating, 10 reviews

Luxurious Lincoln Park Home with Gourmet Kitchen

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.

Apartment in Chicago

5 out of 5 average rating, 4 reviews

Urban Oasis: South Shore Chicago

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

4.93 out of 5 average rating, 29 reviews

Hypebeast Experience

The spacious living area features warm wood flooring and large windows that allow natural light to fill the room. Comfortable seating options include a beige sofa and two accent chairs, complemented by decorative wall art, creating a welcoming atmosphere.

Apartment in Chicago

4.32 out of 5 average rating, 38 reviews

420/Pet friendly 3 Bed Loft Apt, Laundry, Parking

A spacious studio features a California King bed with crisp white linens, complemented by warm wooden flooring. A wall-mounted television is positioned across from the bed, while the kitchen area is visible in the background, showcasing sleek stainless-steel appliances.

Apartment in Chicago

4.89 out of 5 average rating, 27 reviews

Luxe Studio - Cal King Bed - Easy & Free Parking!

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

4.85 out of 5 average rating, 53 reviews

Rooftop HotTub As Seen On "Married At First Sight"

Apartment in Chicago

4.55 out of 5 average rating, 29 reviews

Beautiful 2BR Duplex (2 floors) 4/20 Friendly!

Apartment in Bellwood

4.91 out of 5 average rating, 11 reviews

Bellwood Getaway

Smoking friendly house rentals

The exterior of the home is showcased, featuring a light-colored facade complemented by neatly trimmed shrubs. Stairs lead up to a welcoming entrance, while a well-kept lawn and mature trees provide shade. The roofline is distinctive, adding character to the overall appearance.

Home in Oak Park

4.8 out of 5 average rating, 5 reviews

Spacious Designer Oasis: Game Room - Yard - Garage

4.63 out of 5 average rating, 59 reviews

Nature retreat hide n seek private suite/ house

A modern kitchen showcases natural wood cabinetry and a spacious island featuring a light countertop. Stainless steel appliances are situated against a mosaic backsplash, with bar stools positioned at the island. Warm lighting enhances the inviting atmosphere of the room.

Home in Merrillville

4.29 out of 5 average rating, 7 reviews

Cozy Ranch minutes from I-65 and US 30

The living room features a bright blue color scheme with plush velvet sofas and accent chairs. A glass coffee table is set on a round rug, and natural light filters through the windows, enhancing the space's open feel. A flat-screen TV is mounted on the wall.

4.87 out of 5 average rating, 45 reviews

The Blue House: Family Retreat

A modern kitchen is displayed featuring stainless steel appliances, including a refrigerator and stove. White cabinetry contrasts against warm wood flooring, while a small dining table with black chairs is positioned in the foreground. Natural light enhances the inviting ambiance.

Home in Richton Park

4.71 out of 5 average rating, 14 reviews

Spacious Split-Level Home 30 mins From Downtown!

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

A charming two-story house is showcased with blue siding and white trim. The front porch features white railings and steps leading to the entrance. Flanking the porch, shrubs and a tree provide a touch of greenery, enhancing the welcoming facade.

Home in Chicago

4.54 out of 5 average rating, 26 reviews

Cheerful 4 bedroom, 3 bathroom spacious home

Smoking friendly condo rentals

A modern kitchen is showcased with stainless steel appliances, including a large refrigerator. The spacious island features unique circular stools, and overhead pendant lights provide illumination. A glimpse of the living area is seen in the background, contributing to an open layout.

Private room in Chicago

4.88 out of 5 average rating, 297 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

4.2 out of 5 average rating, 5 reviews

voco: Balcony & City View

Condo in Chicago

5 out of 5 average rating, 55 reviews

Where you want to BE! Stylish, Comfy, Luxe

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, 84 reviews

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

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

Condo in Chicago

4.95 out of 5 average rating, 44 reviews

Beautiful Condo in North Kenwood with Parking

The modern kitchen features stainless steel appliances, an island with circular stone stools, and sleek cabinetry. Pendant lights hang above, illuminating the space, while natural light filters in from the adjacent living area through glass doors.

Private room in Chicago

4.89 out of 5 average rating, 260 reviews

Private BR in Chicago - Dwntwn & Fulton Mkt close

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