Smoking-friendly holiday rentals in Downtown Chicago

Find and book unique smoking-friendly rentals on Airbnb

Top-Rated Smoke-Friendly Accommodation in Downtown Chicago

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

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Guest favourite

Apartment in Chicago

5 out of 5 average rating, 10 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 🍀 Enjoy your 420 experience in our living/dining room or patio 🚙 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

Guest favourite

Home in Chicago

4.96 out of 5 average rating, 180 reviews

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

Guest favourite

Apartment in Chicago

4.96 out of 5 average rating, 117 reviews

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.

Guest favourite

Home in Oak Park

4.92 out of 5 average rating, 24 reviews

Spacious Designer Oasis: Game Room - Yard - Garage

Step into the spacious 5BR 3BA designer getaway in the friendly Oak Park area, just 10 minutes to downtown Chicago via the I-290 and the nearby Blue Line. It promises a relaxing retreat just a stone's throw away from restaurants, shops, exciting attractions, and landmarks. The luxurious design and a rich amenity list will leave you in awe. ✔ 5 Comfortable BRs ✔ Open Design Living ✔ Full Kitchen ✔ Game Room ✔ Fenced Backyard ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Garage Parking Learn more below!

Superhost

Home in Chicago

4.83 out of 5 average rating, 82 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, 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

Guest favourite

Guest suite in Chicago

4.9 out of 5 average rating, 118 reviews

1 bed apartment + futon room bridgeport

Located at the geographic center of Chicago! Plenty of free street parking. Very safe and ~10 min walk to the 35th Orange line and 3 blocks from the Archer bus, both go directly downtown within minutes. Brand new lower level construction unit. Comfortable spacious rooms to relax in. Closet in both rooms for your use while here. The apartment has a separate entrance, bathroom, kitchen, dining space. Enjoy your own private space in Chicago with a back patio, grill, and laundry.

Guest favourite

Apartment in Chicago

4.9 out of 5 average rating, 10 reviews

Stylish 420-3BR Getaway Near McCormick&Grant Park

🌟 Welcome to The State Suite — Premier Downtown Chicago Stay! 🌟 📩 MESSAGE US for SPECIAL RATES! 🚬 Smoking allowed inside 📍 Prime State Street location 🚶‍♂️ Minutes walk to McCormick Convention Center 🔒 Safe building with 24/7 security 🛏️ 3 Queen bedrooms + sofa bed (sleeps 8) 🛁 2 full bathrooms ⚡ Dedicated 250 Mbps internet 📺 4K Roku HDTV 🍳 Fully equipped kitchen 🚗 Optional parking $30/day 🧺 In-unit washer & dryer 🚶‍♂️ Close to all top Chicago attractions!

Top Guest favourite

Guest suite in Chicago

4.95 out of 5 average rating, 174 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

Apartment in Chicago

4.95 out of 5 average rating, 710 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 favourite

Guest suite in Chicago

4.89 out of 5 average rating, 139 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

Loft in Chicago

4.83 out of 5 average rating, 265 reviews

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

Superhost

Apartment in Chicago

New place to stay

The Courtyard Escape

Welcome to The Courtyard Escape in Pilsen! This freshly renovated unit is accepting pre-bookings and will soon showcase updated photos. Featuring a queen bed and queen sofa bed, it’s perfect for couples, friends, or small groups. Enjoy a modern kitchen, cozy living space, and private courtyard with string lights. Step outside and explore one of Chicago’s most exciting neighborhoods, filled with art, culture, and amazing food.