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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Superhost

Apartment in Portage Park

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

Superhost

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 Wicker Park

4.74 out of 5 average rating, 38 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

Guest favorite

An open living area features a spacious sectional sofa centered on an intricately patterned rug. Floor-to-ceiling glass doors provide access to the outdoor patio, while indoor plants add a touch of greenery. A ceiling fan and modern lighting enhance the comfortable space.

Home in North Park

4.96 out of 5 average rating, 170 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

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 South Shore

4.95 out of 5 average rating, 106 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.

Superhost

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…

Guest favorite

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 McKinley Park

4.89 out of 5 average rating, 103 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 spacious outdoor area is covered by a wooden pergola, featuring artificial grass underfoot. Hanging chairs are visible, along with various plants that add greenery to the space. The area is well-lit by natural light through the surrounding openings.

Apartment in Lake Zurich

4.94 out of 5 average rating, 138 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

Home in Carol Stream

4.91 out of 5 average rating, 104 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 favorite

Guest suite in Portage Park

4.94 out of 5 average rating, 159 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

Guest favorite

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, 12 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, 695 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 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 West Town

4.91 out of 5 average rating, 111 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