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Smoking friendly vacation rentals in Northwest Side

Find and book unique smoking friendly rentals on Airbnb

Top-rated smoking friendly rentals in Northwest Side

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 private hot tub is set on a rooftop deck, featuring bubbling water and a city skyline backdrop. Plush seating with soft cushions is arranged nearby, creating a comfortable space for relaxation. The view includes various high-rise buildings against a colorful sky.

Apartment in Chicago

4.85 out of 5 average rating, 53 reviews

Rooftop HotTub As Seen On "Married At First Sight"

This Penthouse is the most unique spot you’ll find near downtown with 2 enormous rooftop decks that offer a fully private 6-person hot tub & the best views of the Chicago skyline! The home is in the posh Bridgeport neighborhood where you can walk to White Sox stadium in less than 5 minutes, or enjoy being immersed in the rich culture of the area which is family-friendly, yet packed with bars & restaurants for daytime & nightlife enjoyment! Once you arrive, we guarantee you won't want to leave!

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.

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, 137 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, 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, 692 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."

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Popular amenities for Northwest Side 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, 9 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, 3 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, 37 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!

A modern living area features a colorful patterned chair alongside a sleek gray sofa. A glass coffee table rests on a vibrant area rug. Warm light is provided by a stylish chandelier, while natural light pours in through large windows framed by light curtains.

Apartment in Chicago

4.64 out of 5 average rating, 56 reviews

McCormick Place 420 friendly 3Br/2Ba opt Parking

Apartment in Chicago

4.55 out of 5 average rating, 29 reviews

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

Apartment in Bellwood

4.9 out of 5 average rating, 10 reviews

Bellwood Getaway

Smoking friendly house rentals

4.67 out of 5 average rating, 58 reviews

Nature retreat hide n seek private suite/ house

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, 99 reviews

A Cozy Room for Two in Vibrant Logan Square

A spacious living room features a large gray sectional sofa positioned around a flat-screen television mounted on the wall. Soft lighting is provided by wall sconces, and three windows with blinds allow natural light to enter. A front door is visible in the background.

Home in Chicago

New place to stay

Bright & Comfy 2BR|West Side Gem

A living room features a dark leather sectional sofa positioned beside a light-colored area rug. A wooden media console is displayed along the wall, adorned with decorative items. A wall-mounted television offers a focal point, while natural light filters through window blinds.

Home in Hazel Crest

New place to stay

NJB & TeasandTacos Luxury Rentals

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, 43 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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