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 modern kitchen countertop displays a sleek air fryer beside a stainless steel toaster. The appliances are set against a backdrop of white tile and dark cabinetry, with gold accents on the hardware adding a touch of elegance.

Home in North Park

4.96 out of 5 average rating, 174 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

Apartment in South Shore

4.95 out of 5 average rating, 111 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

A utility area features a combination washer and dryer adjacent to a small desk with a rolling chair. Brightly colored elephant artwork is displayed on the wall, and a white closet door is visible, contributing to a functional yet inviting space.

Guest suite in Arlington Heights

4.92 out of 5 average rating, 51 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.

Superhost

A wooden media console with barn-style sliding doors encloses a modern electric fireplace. The floor underneath is made of polished hardwood, and various board games are visible on the shelf above the fireplace.

Apartment in Thornton

4.86 out of 5 average rating, 22 reviews

Your quiet south suburban oasis

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 spacious backyard features a wooden deck with a pink picnic table and two blue chairs. Flower beds and a fire pit are visible among the greenery. A grill and a small stone area are also included, surrounded by a privacy fence.

Guest suite in McKinley Park

4.9 out of 5 average rating, 110 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.

Guest favorite

A sheltered pavilion provides a view of a serene lake, framed by lush green trees. Several picnic tables are arranged on the grassy area, and a kayak is seen gliding across the water in the distance. The space appears inviting for outdoor gatherings.

Apartment in Lake Zurich

4.94 out of 5 average rating, 144 reviews

Take A Pebble Apartments Apt#4 (1 Bedroom)

Come stay at Take a Pebble apartments located in downtown Lake Zurich, Illinois. Only a 2 minute walk to our lake. Breakfast, Fast Food, Fine Italian/Pizza Restaurant & a few Bars all in our downtown area. Parking is at a public lot just 90 seconds from the entrance. Below your room is Offbeat Music & LP Records. Take a few records back home with you or better yet a Drum Set!!! Take A Pebble Properties was named after a song by the great band Emerson Lake & Palmer.

Top guest favorite

Guest suite in Portage Park

4.95 out of 5 average rating, 165 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 kitchen area features light-colored cabinetry and a large island with a granite countertop. Stainless steel appliances are visible alongside a dining space with a wooden table and chairs, all set against a neutral wall color and bright, natural lighting.

Home in Romeoville

4.93 out of 5 average rating, 15 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, 700 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

The hallway features polished wooden floors and exposed brick walls, complemented by large windows allowing natural light. A wooden reception desk is positioned against the wall, with a mounted television above. Two lamps provide ambient lighting beside a seating area with a bench and small table.

Guest suite in West Town

4.9 out of 5 average rating, 123 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 Chicago

4.82 out of 5 average rating, 255 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

Guest favorite

An outdoor patio is illuminated by soft lighting under a protective shelter. Comfortable seating arrangements include folding chairs and metal benches. In the center, a fire pit is surrounded by stones, with flames providing warmth and a calming ambiance during the evening.

Home in Chicago Ridge

4.91 out of 5 average rating, 144 reviews

Quiet cul-de-sac with huge fenced in backyard

3 bedroom, 2 bath ranch home on a quiet cul-de-sac. Big fenced in backyard for the kids, dog, & adults to play during the day, then relax by the fire at night. Walking distance (50 ft.) to the bar/restaurant with private entrance. 15 miles (25 mins) from downtown Chicago. And for you couples, come back home from your busy day, sit back and relax in the 8 jet jacuzzi whirlpool tub that will comfortably fit both of you.