Smoking friendly vacation rentals in Chicago

Apartment in Humboldt Park

A welcoming living area features a red sectional couch with decorative cushions and a dark gray sofa. A coffee table holds a collection of magazines and a small tabletop game. Light from a nearby lamp brightens the space, complemented by wall art depicting a cityscape.

4.7 out of 5 average rating, 20 reviews

Heart of Logan Square easily Walk to Dining & Fun

Experience the heart of Logan Square! Swanky 2BR/1BA first floor apartment with a private deck in a multi-unit family building. Walk to Armitage Ave’s top spots, Giant, Moonlighter, Carson’s Chicken, Scofflaw, Rosa’s Blues Bar, Stan Mansion, Cafe Mustache and more! Close to Palmer Square, 606 trail, Blue Line, Bucktown, and Wicker Park. Fully equipped kitchen, 70” Smart TV, washer/dryer, easy self-check-in, and free street parking. No parties please per Chicago regulations. Book your stay today!

Guest suite in McKinley Park

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.

4.91 out of 5 average rating, 128 reviews

Cozy 1BR + Futon • Deck • Laundry • Private Entry

Located at the geographic center of Chicago with plenty of FREE street parking. The area is very safe and about a 10-min walk to the 35th/Archer Orange Line and just 3 blocks from the Archer bus—both take you downtown within minutes. This lower-level 1BR has a private entrance, spacious queen bedroom, living room with full futon, full kitchen, and private bath. Perfect for solo stays, couples, small families, or work trips. Enjoy your own space with access to a back patio, grill, and laundry.

4.96 out of 5 average rating, 191 reviews

Home in North Park

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

4.96 out of 5 average rating, 121 reviews

Apartment in South Shore

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.

4.82 out of 5 average rating, 34 reviews

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

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 suite in Arlington Heights

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.

4.93 out of 5 average rating, 59 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 suite in Portage Park

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.

4.95 out of 5 average rating, 178 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

5 out of 5 average rating, 9 reviews

Apartment in Chicago

Winter Escape|Near DePaul|Free parking+AC/Heat

1 king, 1 queen, and 1 airbed Self Check-in 24/7 support Super host property Central AC and Heat Fully stocked kitchen Bathroom w/ fresh towels & essentials 1 FREE parking spot (a rare find in the city!) This charming and fully equipped 2-bedroom apartment is perfect for couples, families with kids, business travelers, or university visitors. Located just steps from DePaul University, enjoy the walkable lifestyle of one of Chicago's most vibrant neighborhoods.

5 out of 5 average rating, 17 reviews

A charming single-story brick home is displayed with a welcoming front porch under a peaked roof. A fenced yard surrounds the property, and a manicured lawn leads up to the entrance. Natural light brightens the facade, with shadows cast from nearby trees.

Home in South Side

Chicago's Finest Airbnb/airport shuttle/ tours.

Unwind in a spacious, beautifully designed home with a private 420-friendly backyard lounge made for fun and comfort. Featuring a modern kitchen, 85" TV, fireplace, jacuzzi tub, and remote-controlled bedroom AC, this stylish property is just minutes from downtown, university of Chicago hospital and the beach. The backyard includes a large gazebo, luxurious patio furniture, pool table, card table, and TV—your perfect spot to relax and unwind.

Apartment in Logan Square

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.

4.95 out of 5 average rating, 724 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 suite in River West

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.

4.88 out of 5 average rating, 164 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

4.84 out of 5 average rating, 273 reviews

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 Bucktown

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

Popular amenities for Chicago smoking friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Smoking friendly apartment rentals

Apartment in Calumet City

A vibrant green wall features an assortment of decorative mirrors and picture frames in varied shapes. A sleek yellow console table is positioned beneath, adorned with a decorative object and a potted plant. A transparent chair complements the modern aesthetic.

4.78 out of 5 average rating, 36 reviews

The Green Lantern

Apartment in South Loop

4.76 out of 5 average rating, 34 reviews

420-Friendly 2BR Chicago Retreat Near McCormick

A charming house stands amid a lush garden, featuring a variety of plants and shrubbery. Straw and natural materials create beds for growing vegetables. Sunlight filters through the trees, illuminating the scene, while the structure showcases a welcoming porch and a pitched roof.

Apartment in Chicago

4.81 out of 5 average rating, 140 reviews

Studio Apartment in Nature Sancturary

Apartment in West Town

4.64 out of 5 average rating, 47 reviews

The Hype Loft | Parking • Walk to United Center

A well-lit kitchen area features wooden cabinetry, a gas stove, and a sleek countertop. A small plant sits on the counter, while a clock is mounted above the stove. Natural light streams through a nearby window, illuminating the inviting space.

Apartment in Franklin Park

4.55 out of 5 average rating, 11 reviews

Cozy Apartment in Franklin Park

Apartment in Brighton Park

A spacious living area is showcased with a comfortable couch and a flat-screen television positioned on a media console. Light wood flooring leads to an adjacent dining area with a set of chairs and a table, enhancing the open layout.

4.88 out of 5 average rating, 8 reviews

Smokers Preferred 420 friendly

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 Bridgeport

4.82 out of 5 average rating, 62 reviews

Seasonal Discounts. Hot Tub Open Upon Request!

Apartment in South Loop

4.64 out of 5 average rating, 11 reviews

420-Friendly 3BR Oasis Near UIC, McCormick Place

Smoking friendly house rentals

An outdoor patio area features a long wooden table surrounded by eight light-toned chairs. Potted plants add greenery, and a bar area with stools can be seen in the background. A blue umbrella provides shade, enhancing the inviting setting.

Home in Berwyn

Music Hot Spot Three Level Home

4.94 out of 5 average rating, 34 reviews

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

Spacious Designer Oasis: Game Room - Yard - Garage

Home in Lemont

4.54 out of 5 average rating, 72 reviews

Nature retreat hide n seek private suite/ house

Home in Gresham

4.2 out of 5 average rating, 5 reviews

4/20 Friendly 12 PM Check Out 1 Bedroom Basement

Private room in Logan Square

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.

4.87 out of 5 average rating, 108 reviews

A Cozy Room for Two in Vibrant Logan Square

The exterior of the home features a two-story design with a landscaped front yard. Double front doors with decorative glass accents welcome guests. Neatly trimmed bushes and a stone pathway lead to the entrance, framed by a grassy lawn and a clear blue sky.

Home in Markham

fun place for family and friends

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

4.83 out of 5 average rating, 23 reviews

Rejuvenate: 4BR, fenced yard

Home in Chicago

New place to stay

Bronzeville Jazz room. Beautiful, cozy, centered.

Smoking friendly condo rentals

Private room in West Town

A spacious living area features a modern sectional sofa in warm tones, positioned around a circular coffee table. Large windows allow natural light to fill the room, showcasing a view of the outdoors. A neutral area rug anchors the seating arrangement, enhancing the home’s contemporary design.

4.89 out of 5 average rating, 335 reviews

Private BR in Condo close to Chicago Dwtwn!

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.

Condo in South Shore

4.57 out of 5 average rating, 35 reviews

Urban Oasis: South Shore Chicago

5 out of 5 average rating, 61 reviews

A well-lit hallway is adorned with framed artwork and a stylish console table. At the end of the hallway, a cozy seating area with a round dining table and four chairs is visible, illuminated by natural light from large windows.

Condo in Edgewater

Where you want to BE! Stylish, Comfy, Luxe

Private room in West Town

A spacious living area is showcased with a modern leather sectional sofa and a circular coffee table. Large windows allow natural light to fill the room, while decorative wall art and an elegant chandelier enhance the ambiance. A cozy area rug adds warmth to the wooden floor.

4.8 out of 5 average rating, 107 reviews

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