Smoking friendly vacation rentals in Chicago

Find and book unique smoking friendly rentals on Airbnb

Top-rated smoking friendly rentals in Chicago

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

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Guest favorite

Home in North Park

4.96 out of 5 average rating, 152 reviews

Chicago River House with private patio!

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 illuminating seats

Guest favorite

Home in Austin

4.89 out of 5 average rating, 53 reviews

Brand New Spacious Duplex

ZERO CLEANING FEE, NO EVENTS/NO PARTIES NO CHICAGO RESIDENTS This stylish place to stay is perfect for group trips. Minutes away from downtown Oak Park and downtown Chicago. Great open floor plans to accommodate groups of any size. Walking distance from public transportations. Plenty of parking near facility. Great backyard space with fire pit for nice summer nights. In unit laundry, bar, and projector in the lower level space for entertainment. Plenty of space for small to mid sized groups.

Guest favorite

Rental unit in Lake Zurich

4.98 out of 5 average rating, 177 reviews

Take A Pebble Apartments (Studio 3)

Greetings travelers! Come stay in my Studio Apartment located in downtown Lake Zurich, Illinois. A 2 minute walk to our lake. Breakfast Place, Fast Food, Fine Italian/Pizza Restaurant & a few Bars all in our downtown area. Below your room is Offbeat Music & LP Records. Take a few records back home with you or better yet a Drum Set!!! Free parking is available at a public lot just a 90 seconds away. Take A Pebble Properties was named after a song by the great band Emerson Lake & Palmer.

Superhost

Rental unit in Cicero

4.86 out of 5 average rating, 80 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 favorite

Rental unit in South Shore

4.95 out of 5 average rating, 98 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 favorite

Guest suite in McKinley Park

4.91 out of 5 average rating, 95 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 favorite

Home in Carol Stream

4.91 out of 5 average rating, 99 reviews

Lake House Hot Tub-Billiards-Kayak Waterfront Stay

Our beautiful home is the perfect place to gather with friends & family, relax, refresh, fish, have fun with your loved ones. It's the perfect home away from home with great views of the lake and on a quiet cul-de-sac. Stunning views of the lake while grilling or the firepit from the completely upgraded patio & the hot tub 🥂 🐶Up to 2 furry babies are allowed & they'll love the almost 1 acre fenced-in yard! (pet fee is extra & must be included at time of booking)

Guest favorite

Guest suite in Portage Park

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

Rental unit in Near South Side

4.8 out of 5 average rating, 59 reviews

McCormick Place 420 friendly 3BR/2BA/opt parking

• MESSAGE US for SPECIAL RATES • Smoking inside the unit allowed • State street location • Minutes walk to McCormick Convention Center • Safe building monitored by our Security team • 3 Queen size bedrooms for a comfortable stay for 6 guests • 2 full bathrooms for our guests convenience • Dedicated 250 Mbps Internet • 4K Roku HDTV • Fully equipped kitchen • Minutes to all touristic destinations • Optional Parking space for only $30/day • In-unit washer and dryer

Guest favorite

Rental unit in Logan Square

4.95 out of 5 average rating, 679 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 favorite

Loft in Logan Square

4.81 out of 5 average rating, 235 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 favorite

Home in Chicago Ridge

4.93 out of 5 average rating, 101 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.