Smoking-friendly vacation rentals in Cook County

Find and book unique smoking-friendly rentals on Airbnb

Top-rated smoke-friendly accommodations in Cook County

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

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Superhost

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.

Apartment in Calumet City

4.9 out of 5 average rating, 42 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.

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

4.89 out of 5 average rating, 143 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.

Superhost

Apartment in Chicago

New place to stay

Cozy smoking unit Downtown | McCormick | Lakefront

When you step inside this bright South Loop apartment, the city instantly fades behind you. Light filters in through the windows, warming the hardwood floors, and the quiet hum of the space feels like a soft welcome. You breathe deeper. You feel the comfort settle in. This is where your Chicago days begin—and where they gently end. Just minutes from McCormick Place, museums, restaurants, and transit, this home offers the mix of convenience, comfort, and privacy right in the heart of the city.

Guest favourite

Apartment in Chicago

5 out of 5 average rating, 13 reviews

“The Sunflower Suite” 420 Friendly - Free Parking

✨🌻✨Welcome to The Sunflower Suite - Private Apartment. 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 couple, small family or group of friends 🎸LoLLapaLooZa & RIOT Fest’s fans favorite 🍀420 friendly🍀 🚙 FreeParking and own main door access code to check-in at ANY time after 3 p.m. no-hassle check-in guaranteed 🏡 Safe neighborhood with restaurants & stores

Superhost

A three-story home is shown with a light-colored exterior and blue accents. A staircase leads up to a covered entryway. Surrounding space includes a driveway for parking and neighboring buildings, along with a well-maintained yard featuring colorful shrubbery.

Home in Chicago

4.84 out of 5 average rating, 86 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

4.83 out of 5 average rating, 36 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.

Camper/RV in Gary

4.88 out of 5 average rating, 64 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

4.95 out of 5 average rating, 76 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

A round marble table is centered in a light-filled dining area, surrounded by four gray chairs. Natural light enters through a large window, highlighting the wood flooring and soft color palette of the walls. A cozy nook in the background offers additional seating.

Bungalow in Streamwood

4.92 out of 5 average rating, 60 reviews

Tranquil tiny cottage by golf club-senior friendly

Before every reservation this home is professionally CLEANED and SANITIZED from top to bottom! This is a little single-family home on a corner near a golf course. A Charming tranquil one story private 2 bed 1 bath cottage recently remodeled last year from top to bottom. There is a separate patio area with umbrella patio set and grill for your use. senior friendly with 1 step- wide doorways more details in listing… * one of driveways can accommodate a 25” horse trailer #847-

Top 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, 108 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 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.

Guest suite in Chicago

4.88 out of 5 average rating, 199 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

Guest favourite

A corner jacuzzi whirlpool tub is positioned against a wall, featuring multiple jets for relaxation. A white toilet and a small wooden stool are visible nearby. Light gray walls are complemented by a window covered with a light-colored curtain, allowing natural light to filter in.

Home in Chicago Ridge

4.9 out of 5 average rating, 197 reviews

Quiet cul-de-sac with huge fenced in backyard

3 bedroom, 2 bath ranch home on a quiet cul-de-sac. Big fenced in backyard for the kids, dog, & adults to play during the day, then relax by the fire at night. Walking distance (50 ft.) to the bar/restaurant with private entrance. 15 miles (25 mins) from downtown Chicago. And for you couples, come back home from your busy day, sit back and relax in the 8 jet jacuzzi whirlpool tub that will comfortably fit both of you.