Smoking friendly vacation rentals in Chicago

Apartment in Calumet City

A comfortable living area features a spacious gray sectional sofa adorned with decorative pillows. A small coffee table sits atop a colorful area rug, and artwork is displayed on the wall. Natural light enhances the calm atmosphere of the space.

4.9 out of 5 average rating, 31 reviews

Welcome to True Blue.

Relax with the whole family at this peaceful place to stay. A stylish, great work space, with great dining and entertainment nearby. True Blue is located in the heart of everything, 15 minutes away from downtown Chicago, 20 minutes away from Joliet. Right next door to northwest Indiana. Come relax and enjoy this amazing home away from home smoking is allowed inside of home. Please no large parties or gatherings or loud music there is a 500 dollar fee smoking is allowed inside and outside of home

4.8 out of 5 average rating, 20 reviews

Home in South Side

420-Friendly 2BR Retreat • Private Yard Near DT

Welcome to Chicago’s Finest Getaway. A stylish and relaxing retreat just 10–15 minutes from downtown. Enjoy two queen bedrooms, a cozy living room with an 85” smart TV and fireplace, a modern kitchen, and a jacuzzi tub. Step into your private 420-friendly backyard lounge with a gazebo, luxury seating, pool table, and outdoor TV. Perfect for families, couples, and weekend explorers looking for comfort, privacy, and easy access to Chicago’s top attractions.Optional airport transportation available

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.

4.9 out of 5 average rating, 133 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, 197 reviews

Home in North Park

The Chicago River House – GIANT wall projector!

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, 123 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.

Apartment in Humboldt Park

4.89 out of 5 average rating, 44 reviews

Artist Lofty Garden in Humboldt Park - 2BR + games

Welcome to your urban oasis in Humboldt Park, where the local’s live! Lofty, open-concept living with exposed brick walls, and lower ceilings: • 2BR, 1 Bathroom + futon • Fully equipped kitchen • Chill vibes 🌿 • 2.4GHz guest WiFi-great for emails, & light work • Access to lush backyard • Free easy street parking 1/2 block away • On-site vending machine & free laundry Reasonable loud levels at night is not a problem. You will also hear the upstairs neighbors footsteps & occasional dog barks.

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.

4.94 out of 5 average rating, 65 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, 183 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, 17 reviews

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.

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, 729 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.

4.87 out of 5 average rating, 173 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

Popular amenities for Chicago smoking friendly rentals

Kitchen

Wifi

Free parking on premises

Air conditioning

Smoking friendly apartment rentals

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.

4.82 out of 5 average rating, 142 reviews

Studio Apartment in Nature Sancturary

Apartment in South Loop

4.82 out of 5 average rating, 17 reviews

Spacious 3BR 420-Friendly | McCormick & UIC Campus

4.9 out of 5 average rating, 10 reviews

Cozy 420-Friendly Downtown | McCormick | Lakefront

New place to stay

Gameroom - Best family gathering option in Chicago

Apartment in Greater Grand Crossing

Apartment in Bridgeview

Executive Retreat Gym Sauna Whirlpool Steam Shower

The living room features warm-toned furniture, including a cozy sofa and patterned chairs. Natural light fills the space through large windows, accentuating the polished wood floors. A decorative wall art piece adds a personal touch, while a small table centers the seating area.

4.51 out of 5 average rating, 72 reviews

2 BR•420 & Pet Friendly•Long/Short Term•Parking

A spacious kitchen is seen through an archway. Bright white cabinets contrast with the dark countertops. An island with a sink is centrally positioned, surrounded by modern appliances. Natural light filters through a nearby window, enhancing the open and airy layout.

Apartment in Little Village

4.76 out of 5 average rating, 34 reviews

Luxury Villa 10 mins to Downtown

4.86 out of 5 average rating, 22 reviews

Cozy Unit +Kitchen & DW Parking - Quiet Area

Smoking friendly house rentals

4.45 out of 5 average rating, 74 reviews

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

Home in Lemont

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

A spacious living room features a sectional sofa adorned with decorative pillows. Light filters through large windows, illuminating the hardwood floor. A cozy area rug is placed beneath a coffee table, and a dining set is visible in the background, enhancing the room's inviting layout.

Home in Hazel Crest

Cheerful 2 bedroom sunny single family home

A welcoming entrance to the property is depicted, featuring a brick facade and large windows. A round lamp post stands at the front, casting a soft glow, while the front door is framed by a small step leading up from the sidewalk.

Private room in Chicago

4.1 out of 5 average rating, 10 reviews

Room3

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

4.85 out of 5 average rating, 26 reviews

Rejuvenate: 4BR, fenced yard

Home in Chicago

4.67 out of 5 average rating, 3 reviews

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.

4.88 out of 5 average rating, 339 reviews

Private BR in Condo close to Chicago Dwtwn!

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

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

4.63 out of 5 average rating, 40 reviews

Urban Oasis: South Shore Chicago

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.

4.81 out of 5 average rating, 108 reviews

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