Smoking-friendly holiday rentals in Cook County

Find and book unique smoking-friendly rentals on Airbnb

Top-Rated Smoke-Friendly Accommodation in Cook County

Guests agree: These smoking-friendly rentals are highly rated for location, cleanliness and more.

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Superhost

Home in Chicago

4.83 out of 5 average rating, 23 reviews

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 favourite

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.

Guest suite in Chicago

4.91 out of 5 average rating, 137 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.

Top Guest favourite

Home in Chicago

4.96 out of 5 average rating, 197 reviews

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

Superhost

A spacious living room features a large flat-screen television mounted on the wall. Comfortable seating includes a plush sofa and intricately patterned armchairs. Natural light streams through two windows, highlighting the wooden flooring and creating an inviting atmosphere.

Home in Chicago

4.83 out of 5 average rating, 84 reviews

Stunning 4 BR Home * Near many Chicago Landmarks

Stunning 4 BR Home * Chicago * Centrally Located This is the perfect home for a large group traveling to Chicago. With 3 levels of living space, 2 full bathrooms, central air and heat, parking, and a private yard, speakeasy room you can enjoy the company of your friends and family without giving up the comforts of home. Near the expressway. Downtown 7 mi Midway Airport 6 mi Ohare Airport 19 mi Chicago Bulls & Black Hawks 4 mi White Sox Stadium 9 mi Cubs Stadium 12 mi Mccormick Place

Superhost

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

4.82 out of 5 average rating, 34 reviews

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 favourite

Two friendly horses are seen near a metal gate, surrounded by lush green grass and trees. The background features a gently sloping path that leads further into the natural landscape, providing a sense of tranquility and connection with nature.

Campervan/RV in Gary

4.87 out of 5 average rating, 63 reviews

Horse farm with Miller beach parking.

Insta @rocking_horse_camping_ranch Love horses? Fishing? Mother Nature? We are the closest farm out side of Chicago. A hidden, unique property to escape the city life. We have 3 horses, 4 ponies and 5 goats all are very friendly. We have 20 acres of land you would never know is there! Bird watching? The property is located on Calumet river! Amazing fishing and ponds down the block. BEACH PARKING INCLUDED. A 10 minute drive to private parking 3 blocks from the beach. Perfect for just couples.

Top Guest favourite

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.

Guest suite in Arlington Heights

4.94 out of 5 average rating, 67 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

Apartment in Chicago

4.9 out of 5 average rating, 48 reviews

Artist Lofty Garden in Humboldt Park - 2BR + games

Urban oasis in Humboldt Park, where the local’s live! Lofty, open-concept w/ exposed brick walls, & lower ceilings: • 2BR, 1 Bathroom + futon • Fully equipped kitchen • Private space for late-night chill sessions & good vibes 🌿 • 2.4GHz guest WiFi for emails, & light work • Lush backyard • Free easy street parking 1/2 block away • On-site vending machine & free laundry Loud levels at night is not a problem. You will also hear the upstairs neighbors footsteps & occasional dog barks.

Superhost

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.

Apartment in Calumet City

4.8 out of 5 average rating, 40 reviews

The Green Lantern

Relax and unwind with the family or friends at this peaceful place. A stylish 2 bedroom 1 bathroom home that you 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. This home allow’s smoking inside..

Top Guest favourite

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.

Guest suite in Chicago

4.95 out of 5 average rating, 184 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 favourite

A living area is presented with a light-colored sectional sofa and a glass coffee table on a colorful area rug. Two bright windows allow natural light, while a ceiling fan enhances airflow. A small table is positioned beside a bookshelf and television.

Apartment in Chicago

4.91 out of 5 average rating, 106 reviews

Cannabis Condo 4BR

Beautiful, spacious apartment is located 10 min from Beach. 10 mins to Hyde Park, (Tiger Woods) Golf Course. 10 mins from Obama Library (coming soon). 10 mins from Museum of Science and Industry. 20 mins from downtown/Soldiers Field (Bears Stadium), Northernly Island concerts, Field Museum, and Shedd Aquarium (beautiful drive down Lakeshore, Metra Electric Line train, or Bus). 15 min from Indiana casino. Ideal for Summer time Chi or Winter snow Chicago!

Top Guest favourite

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 Chicago

4.95 out of 5 average rating, 730 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."