Smoking friendly vacation rentals in Chicago

Find and book unique smoking friendly rentals on Airbnb

Top-rated smoking friendly rentals in Chicago

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

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Guest favorite

A private outdoor patio is surrounded by wooden fencing, featuring a glowing sofa and two chairs placed on a patterned rug. A small table holds a plant, while greenery adds a natural touch to the tranquil setting, under a colorful sky at dusk.

Home in North Park

4.95 out of 5 average rating, 176 reviews

Chicago River House -BBQ Oasis now open!

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

Guest favorite

The spacious living area features dark wood flooring and a modern ceiling fan. A large flat-screen TV is mounted above a white fireplace. A gray sofa and armchair provide comfortable seating, while a glass coffee table sits in the center, enhanced by artwork on the walls.

Apartment in South Shore

4.96 out of 5 average rating, 113 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.

Guest favorite

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 Austin

4.91 out of 5 average rating, 22 reviews

Spacious Designer Oasis: Game Room - Yard - Garage

Step into the spacious 5BR 3BA designer getaway in the friendly Oak Park area, just 10 minutes to downtown Chicago via the I-290 and the nearby Blue Line. It promises a relaxing retreat just a stone's throw away from restaurants, shops, exciting attractions, and landmarks. The luxurious design and a rich amenity list will leave you in awe. ✔ 5 Comfortable BRs ✔ Open Design Living ✔ Full Kitchen ✔ Game Room ✔ Fenced Backyard ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Garage Parking Learn more below!

Superhost

A spacious living room features a gray sectional sofa and a round area rug, complementing a stylish coffee table at the center. Natural light filters through sheer curtains, while a piece of abstract wall art adds a pop of color. A potted plant adds a touch of greenery.

Apartment in Thornton

4.83 out of 5 average rating, 29 reviews

Your quiet south suburban oasis

NO PARTIES! Relax and enjoy yourself in this south suburban duplex located in a safe and quiet location! We offer the entire unit so you don’t have to worry about sharing. 1 bedroom but the living room is spacious enough for an air mattress (must bring own). Large yard for you and your family to enjoy outdoor activities! Park less than 1 block away. 4 blocks from the famous rock quarry of Thornton. New casino less than 2 miles away. Bar right across the street! Animals allowed if trained.

Guest favorite

A bright living space features a spacious sectional sofa accented with blue and white cushions. A round coffee table sits atop a decorative rug. A large clock adorns the wall, while a dining area with a wooden table and chairs is visible in the background.

Guest suite in Arlington Heights

4.92 out of 5 average rating, 53 reviews

Cozy Chicago Suburban Apartment

Welcome to our cozy apartment, perfect for solo travelers or couples looking for a comfortable stay in the quiet Northwestern suburbs of Chicago. Located in a quiet and serene neighborhood, this apartment offers easy access to all the best restaurants, cafes, and shops. Just 23 mins away from O’hare International Airport, 15 mins to Schaumburg Convention center & Woodfield Mall, and about 40 mins from the Chicago Downtown. Lake Arlington is a 10 mins walk away for Kayak and park activities.

Guest favorite

A cozy bedroom is presented with warm wood flooring and soft lighting. A spacious bed is adorned with neutral bedding, complemented by a decorative bench at the foot. A dresser and artwork decorate the walls, while natural light filters in through small windows.

Guest suite in McKinley Park

4.89 out of 5 average rating, 112 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.

Superhost

A comfortable living area features a blue sectional sofa opposite a modern green chair. A wooden coffee table is centered on a patterned area rug, while two vibrant wall art pieces bring color to the space. Light enters through a tall window, enhancing the atmosphere.

Apartment in Near Southside

5 out of 5 average rating, 6 reviews

Stylish 420-3BR Getaway Near McCormick&Grant Park

🌟 Welcome to The State Suite — Premier Downtown Chicago Stay! 🌟 📩 MESSAGE US for SPECIAL RATES! 🚬 Smoking allowed inside 📍 Prime State Street location 🚶‍♂️ Minutes walk to McCormick Convention Center 🔒 Safe building with 24/7 security 🛏️ 3 Queen bedrooms + sofa bed (sleeps 8) 🛁 2 full bathrooms ⚡ Dedicated 250 Mbps internet 📺 4K Roku HDTV 🍳 Fully equipped kitchen 🚗 Optional parking $30/day 🧺 In-unit washer & dryer 🚶‍♂️ Close to all top Chicago attractions!

Top guest favorite

A brick bungalow features a welcoming front porch adorned with a US flag. The porch includes a railing and seating area, while flower pots add greenery. Stairs lead up to the front door, which is detailed with a decorative screen.

Guest suite in Portage Park

4.95 out of 5 average rating, 170 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

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

4.9 out of 5 average rating, 20 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.

Guest favorite

A bright living room is illuminated by natural light from large windows. A white sofa is paired with two orange chairs, complemented by vibrant cushions. A coffee table with a striped design sits centrally, surrounded by decorative plants and artwork on the walls.

Apartment in Logan Square

4.95 out of 5 average rating, 705 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."

Guest favorite

A living area features exposed brick walls and polished hardwood floors. A comfortable sofa along with two wooden side tables, each topped with a lamp, is positioned for relaxing. Large windows allow natural light to fill the space, providing views of the outdoors.

Guest suite in West Town

4.89 out of 5 average rating, 135 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

Guest favorite

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 Logan Square

4.83 out of 5 average rating, 261 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