Smoking-friendly vacation rentals in Downtown Chicago

Find and book unique smoking-friendly rentals on Airbnb

Top-rated smoke-friendly accommodations in Downtown Chicago

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

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Superhost

Apartment in Chicago

4.85 out of 5 average rating, 53 reviews

Holiday Parties Welcome with 3 nights or more!

This Penthouse is the most unique spot you’ll find near downtown with 2 enormous rooftop decks that offer a fully private 6-person hot tub & the best views of the Chicago skyline! The home is in the posh Bridgeport neighborhood where you can walk to White Sox stadium in less than 5 minutes, or enjoy being immersed in the rich culture of the area which is family-friendly, yet packed with bars & restaurants for daytime & nightlife enjoyment! Once you arrive, we guarantee you won't want to leave!

Superhost

Apartment in Cicero

4.84 out of 5 average rating, 83 reviews

Modern Cicero apartment

The drive is 11minutes from Midway. It is in Cicero, IL. The neighborhood is peaceful with friendly neighbors. 6 guest max in the property. We have street parking.Smoking is allowed please be respectful.Open windows and close vents if you choose to smoke. It has great appliances and the tub comes with a jacuzzi. There is a backyard as well that is shared with the neighbors but can be utilized. We plan to make your stay as comfortable as possible to enjoy your experience in town.420 friendly.

Guest favourite

Guesthouse in Arlington Heights

4.93 out of 5 average rating, 43 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 favourite

Apartment in Chicago

4.95 out of 5 average rating, 100 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 Chi on Lake Shore Drive Beaches. Lollapalooza. Riotfest. Bears during football season. Winter wonder festival. Great food. Great for larger groups visiting looking to divide costs. Obama Library, golf course, Reggies on the Beach, Soldiers Field, Shedd Aquarium, Field Museum, Museum of Science & Industry are within 20 minutes.

Guest favourite

Apartment in Chicago

4.94 out of 5 average rating, 49 reviews

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

420 friendly 1 BD with 2 queen beds in room , a full size roller and a full luxury quiet office space with a twin bed. Great for business trips with team or individual/couples looking for peace and luxury. Above average location. NO PARTIES ALLOWED! NO PETS ALLOWED! I am allergic to cats and dogs. All guests staying overnight MUST be added to your reservation. Early check in/late check out may be available for fee unless otherwise agreed upon. Contact the host for any inquiries.

Superhost

Home in Chicago

4.81 out of 5 average rating, 68 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

4.91 out of 5 average rating, 97 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

Guest suite in Chicago

4.95 out of 5 average rating, 149 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

Superhost

Apartment in Chicago

4.81 out of 5 average rating, 117 reviews

McCormick Pl 420 friendly 1br/1ba parking/sleeps 4

• MESSAGE US for SPECIAL RATES • Minutes walk to McCormick Convention Center • 420 friendly unit. Smoking inside the unit allowed • Optional Parking space • State street location • Safe building monitored by our Security team • Queen size bedroom + Sofa bed for a comfortable stay for up to 4 guests • Dedicated fast Internet • 65" 4K Roku Smart HDTV(Roku and Netflix) • Fully equipped kitchen • Minutes to all touristic destinations • In-unit washer and dryer

Guest favourite

Apartment in Chicago

4.95 out of 5 average rating, 681 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

Loft in Chicago

4.81 out of 5 average rating, 236 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

Guest favourite

Home in Chicago Ridge

4.93 out of 5 average rating, 106 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.