Smoking-friendly holiday rentals in Chicago

4.89 out of 5 average rating, 144 reviews

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

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.

BackyardQuietCondition

Apartment in Humboldt Park

4.91 out of 5 average rating, 57 reviews

Artist Lofty GAME Garden-Humboldt Park 2BR Cozy

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 • Bluetooth Soundbar 🎵🎥 Loud levels at night is not a problem. You will also hear the upstairs neighbors footsteps above.

BackyardQuietIndoor spaces

4.96 out of 5 average rating, 200 reviews

Home in Chicago

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

BackyardQuietBarbecue

Apartment in Portage Park

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

Outdoor spacesBackyardComfort

4.83 out of 5 average rating, 87 reviews

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 West Side

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

BackyardOutdoor spacesAir conditioning

4.9 out of 5 average rating, 10 reviews

Apartment in Chicago

City Retreat

Welcome to your home away from home in the heart of Chicago! This charming, two bedroom home offers a blend of comfort, convenience and accessibility. The vibrant Neighbourhood put you close to local amenities, dining and entertainment. You’ll find excellent restaurant shops, cultural attractions within walking distance. The area is well connected with easy access to public transportation, making it easy to explore what Chicago has to offer. Full cable premium package provided free of charge.

ComfortFamilyHospitality

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, 747 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. Family friendly with additional kid/baby toys and supplies. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 15 years hosting we still enjoy making our space special…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."

Outdoor spacesBackyardComfort

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.

4.95 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.

QuietAir conditioningIndoor spaces

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, 191 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

QuietBackyardBathroom

4.91 out of 5 average rating, 109 reviews

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 South Side

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!

QuietValueGetting around

4.88 out of 5 average rating, 206 reviews

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 West Town

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

Outdoor spacesQuietAccuracy

4.89 out of 5 average rating, 199 reviews

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

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.

Outdoor spacesQuietCheck-in

Popular amenities for Chicago Smoke-Friendly Accommodation

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Smoking-friendly apartment rentals

4.83 out of 5 average rating, 36 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

QuietLocationKitchen

Apartment in Downtown Chicago

4.55 out of 5 average rating, 11 reviews

Loft near McCormick Place w/250Mbps WiFi

QuietCleanlinessSleep quality

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 Humboldt Park

4.82 out of 5 average rating, 148 reviews

Studio Apartment in Nature Sancturary

Outdoor spacesBackyardAmenities

Apartment in Ukrainian Village

4.86 out of 5 average rating, 21 reviews

Peaceful Zen Flat | 2BR Oasis with Free Parking

QuietGetting aroundLocation

Apartment in Downtown Chicago

4.67 out of 5 average rating, 3 reviews

South Loop 2BR smoking allowed/McCormick Place

WalkabilityComfortNearby

A billiards table is positioned in a well-lit area, with a mounted television visible on the wall. Two cues and a set of colorful pool balls are arranged on the table. Wooden cabinetry can be seen in the background, complementing the modern decor.

Apartment in Wicker Park

4.65 out of 5 average rating, 23 reviews

Loft Style Wicker Park Apartment

KitchenTVIndoor spaces

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, 42 reviews

Welcome to True Blue.

QuietComfortGetting around

4.9 out of 5 average rating, 84 reviews

The exterior of a two-story stone house is shown, featuring a brown wooden fence and a concrete walkway leading to the entrance. Large windows allow natural light into the home. A well-maintained lawn is visible in front, complementing the inviting outdoor space.

Apartment in Chicago

420 friendly apt with 2 queens,1 full,1 twin bed

QuietBackyardWalkability

Smoke-Friendly Holiday Houses

New place to stay

Modern Bronzeville Escape @ The Grandeur Estates

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 Oak Park

Music Hot Spot Three Level Home

3.33 out of 5 average rating, 3 reviews

University Gallery - Spacious Home by OPC and DTWN

Home in Harvey

The Queen and Kingdom

QuietBathroomCleanliness

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 Homewood

Cheerful 2 bedroom sunny single family home

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

4.91 out of 5 average rating, 11 reviews

Bronzeville Jazz room. Beautiful, cozy, centered.

QuietHeatingComfort

4.68 out of 5 average rating, 31 reviews

420-Friendly 2BR Retreat • Private Yard Near DT

Outdoor spacesBackyardTV

Smoke-Friendly Holiday Condos

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, 356 reviews

Private BR in Condo close to Chicago Dwtwn!

QuietHot tubHeating

A bright living area features hardwood flooring and natural light from a large window. A projection screen showcasing a serene beach scene dominates one wall. A wooden coffee table and two seating options, including a lounge chair, complement the relaxed atmosphere.

Condo in South Side

3.5 out of 5 average rating, 4 reviews

Hyde Park Sanctuary | Near UChicago & Lakefront

CleanlinessIndoor spacesHospitality

5 out of 5 average rating, 63 reviews

Condo in Edgewater

Where you want to BE! Stylish, Comfy, Luxe

BackyardOutdoor spacesComfort