Smoking friendly vacation rentals in Chicago

Find and book unique smoking friendly rentals on Airbnb

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Popular amenities for Chicago smoking friendly rentals

Smoking friendly apartment rentals

Guest favorite
An outdoor deck area is presented, featuring a table surrounded by four blue chairs. Lush greenery creates a natural border, enhancing the space. An outdoor rug adds texture beneath the seating arrangement, while a staircase is visible in the background.
Apartment in Lincoln Park
5 out of 5 average rating, 9 reviews

Luxurious Lincoln Park Home with Gourmet Kitchen

ShyamRating, 5 stars1 week ago
Loved our stay here. a gorgeous home with a ton of space and top notch finishes. Nestled between Lincoln Park and Boystown, this place was the perfect home base for our group.
A spacious living area features a large sectional sofa draped with a cozy throw. Soft lighting is provided by recessed ceiling lights. A stylish desk and chair are positioned nearby, complementing a picturesque wall-mounted television that serves as a focal point in the room.
Apartment in South Shore
5 out of 5 average rating, 3 reviews

Urban Oasis: South Shore Chicago

DestinyRating, 5 stars4 days ago
I would highly recommend this Ari BnB to anyone coming to Chicago. The host Micheal was very polite and flexible exceeding his hosting abilities. He was available 24/7, proactive and very fast in correcting any small issues in a very timely manner. Polite is an understatement as he made me and the others stay there feel like home and an overall great experience. To add, the inside looked exactly like the pictures and clean all throughout. The best part was that the location was very private and peaceful. Thank You, I will definitely be booking again.
Guest favorite
A spacious living area features a sectional sofa with patterned cushions, a coffee table adorned with magazines, and a foosball table nearby. The kitchen space is visible, showcasing modern appliances and stylish cabinets, while a feature wall adds a unique touch to the room.
Apartment in West Town
4.93 out of 5 average rating, 29 reviews

Hypebeast Experience

BrandonRating, 5 stars1 week ago
Born and raised in Chicago and moved away in 2013. I usually stay with either family or friends when I visit back home, but I wanted some privacy this go round and couldn’t have been happier with this location! It’s in the middle of everything regardless of direction of travel so, it took us no longer than 15-20 minutes to get everywhere we needed to go. There was a small hiccup in checking in, but I reached out to Amy and the hosts were very quick to respond and resolve the issue. I plan on checking this location whenever I come back home from now on. Great spot, Amy!
The spacious living area features warm wood flooring and large windows that allow natural light to fill the room. Comfortable seating options include a beige sofa and two accent chairs, complemented by decorative wall art, creating a welcoming atmosphere.
Apartment in Chicago
4.32 out of 5 average rating, 37 reviews

420/Pet friendly 3 Bed Loft Apt, Laundry, Parking

RenehRating, 5 stars1 month ago
the host was so nice and responsive. super spacious. the place was nice and had extra amenities. the rooms were nice and it was nice knowing it’s a bed under the bunk bed to slide out. the downstairs neighbor was so nice i loved her. i would definitely book again.
Superhost
A spacious studio features a California King bed with crisp white linens, complemented by warm wooden flooring. A wall-mounted television is positioned across from the bed, while the kitchen area is visible in the background, showcasing sleek stainless-steel appliances.
Apartment in East Pilsen
4.89 out of 5 average rating, 27 reviews

Luxe Studio - Cal King Bed - Easy & Free Parking!

MelissaRating, 5 stars1 week ago
Coty was a wonderful host. There was a slight hiccup with there being no hot water but Coty was extremely responsive and kept me in the loop and got the problem fixed. Highly recommend booking Coty’s place if you’re ever in Chicago. Also the family owned taco spot next door serves really good food and is great after a long day of travel.
A modern living area features a colorful patterned chair alongside a sleek gray sofa. A glass coffee table rests on a vibrant area rug. Warm light is provided by a stylish chandelier, while natural light pours in through large windows framed by light curtains.
Apartment in Near South Side
4.64 out of 5 average rating, 56 reviews

McCormick Place 420 friendly 3Br/2Ba opt Parking

KarenRating, 5 stars2 weeks ago
Innesa’s home was very nice. We enjoyed our stay and the location was great for walkability and close enough to restaurants and attractions. We would stay again!
Apartment in South Shore
4.55 out of 5 average rating, 29 reviews

Beautiful 2BR Duplex (2 floors) 4/20 Friendly!

KarenRating, 5 stars10 months ago
Great stay. Host came in the evening to fix cable issue. Appreciated. Location was close to downtown.
Apartment in Bellwood
4.89 out of 5 average rating, 9 reviews

Bellwood Getaway

KhulanRating, 5 stars2 days ago
The place was very clean the host was amazing! We had a great time here and will definitely come back!

Smoking friendly house rentals

Home in Lemont
4.67 out of 5 average rating, 58 reviews

Nature retreat hide n seek private suite/ house

KeithRating, 5 stars1 week ago
It's hard to get this much privacy and peacefulness this close to the city. Lena's home is a great little hidden gem. The location is amazingly quiet and has a great view of the wetlands below it. Lena became a friend I fell in love with her dog. I wouldn't hesitate to stay here for a day, or a month. It's a great little spot.
Private room in Chatham
5 out of 5 average rating, 3 reviews

1st Room @93rd

LuckyRating, 5 stars10 months ago
Just exactly what I needed, a great spot for convenient public transit to get to downtown Chicago each day.
Guest favorite
A spacious living room showcases stylish wooden accents, featuring a glass coffee table on a decorative rug. A comfortable recliner and various entertainment units are visible, while a doorway leads to another area of the home, creating an inviting and open atmosphere.
Private room in Logan Square
4.87 out of 5 average rating, 99 reviews

A Cozy Room for Two in Vibrant Logan Square

AliseRating, 5 stars2 months ago
This was my first experience with a "shared" booking. The house was very charming home and was cozy and comfortable. Justine was an excellent host and extremely friendly, kind and communicative! I really enjoyed my stay and will book this place again! Justine, thank you for sharing your home and making me feel like a family member!
A stylish living area features a large flat-screen TV mounted on the wall, above a sleek media console. A modern mirrored coffee table complements the space, and a bouquet of red roses adds a touch of colour against the neutral backdrop of grey curtains.
Home in Calumet City
4.8 out of 5 average rating, 10 reviews

Cozy Retreat in Calumet City

Brian Keith JrRating, 5 stars2 weeks ago
The host was very responsive and helpful she really made the stay feel as if me and my girl were at home while we threw a little club themed get together for my girlfriends birthday it was great enough space and beds I would most definitely book again in the future and would recommend worth every penny I paid
A charming two-story house is showcased with blue siding and white trim. The front porch features white railings and steps leading to the entrance. Flanking the porch, shrubs and a tree provide a touch of greenery, enhancing the welcoming facade.
Home in Chicago
4.54 out of 5 average rating, 26 reviews

Cheerful 4 bedroom, 3 bathroom spacious home

TosonRating, 5 stars4 months ago
I’m giving this Airbnb 5 stars, but I want to be honest about my experience. While the space overall has its positives, there were several issues that left me less than impressed. Pros: The house is spacious with plenty of room for everyone to spread out. Having three bathrooms was convenient, and the kids really enjoyed the small pool table and other games provided. The layout worked well for our group, and the space had potential. Cons: Unfortunately, there were some major drawbacks. The beds had plastic covers, which made them uncomfortable to sleep on. None of the bedrooms had real dressers or nightstands, which made organizing our belongings a challenge. The water upstairs was extremely hot and didn’t seem to have an option to adjust it, which was a safety concern. Additionally, the furniture was noticeably worn down and could use some updates. Overall, the space is cool and functional, but it felt like it needed a bit more attention to detail and care to make it truly great.
Superhost
A cozy living room area features a large, soft blue bean bag chair positioned near a comfortable brown sectional couch. Natural light enters through an arched window, complemented by patterned drapes. Wall decor includes framed pictures and plants, contributing to a nurturing space.
Private room in Rolling Meadows
4.67 out of 5 average rating, 3 reviews

Large upper floor/3 bedrooms - 2 full bath avail

CarolaRating, 5 stars9 months ago
Victoria is a great host. Her hospitality was amazing and she was very cooperative with everything. I loved her two dogs and my stay there was as expected. Full recommend her as a host.
A modern living area features a dark blue sofa positioned on a light-colored rug. A flat-screen TV is mounted on the wall, and a glass stand is placed beside it. The room connects to a staircase, suggesting multiple levels in the house.
Home in Country Club Hills
4.61 out of 5 average rating, 41 reviews

Entire suburban home 30 mins from downtown Chicago

BriannaRating, 5 stars2 months ago
great over all will stay again when visiting family

Smoking friendly condo rentals

Guest favorite
A modern kitchen is showcased with stainless steel appliances, including a large refrigerator. The spacious island features unique circular stools, and overhead pendant lights provide illumination. A glimpse of the living area is seen in the background, contributing to an open layout.
Private room in West Town
4.88 out of 5 average rating, 297 reviews

Private BR in Condo close to Chicago Dwtwn!

AlveeraRating, 5 stars2 weeks ago
Saurin’s place was super comfortable and felt homely! Location is pretty convenient - with the bus stop / train station being in close proximity. Saurin was super helpful during our stay and prompt in responding to our queries. Would highly recommend his place!
A serene bedroom is illuminated by soft purple lighting. A spacious bed with a polka dot blanket is centered in the room. Floor-to-ceiling glass doors reveal a view of a vibrant city skyline at night, with city lights twinkling in the background.
Condo in The Loop
4.2 out of 5 average rating, 5 reviews

voco: Balcony & City View

GavynRating, 5 stars1 month ago
Overall very nice place for the price. Only disappointment was I got to the location listed on the air bnb listing and the actual location was 3 to 4 blocks away which I was a bit upset with. It is closer to the Chicago station on the redline than it is to the river where the listing states. Host was very responsive and allowed me to check out late to avoid waiting around at the airport for a long time.
Guest favorite
Condo in East Rogers Park
5 out of 5 average rating, 55 reviews

Where you want to BE! Stylish, Comfy, Luxe

EdwardRating, 5 stars6 months ago
This has to be the best AirBnB we have stayed at. The apartment was like home from home, super clean and exceeded our expectations. The location of the apartment is a short walk from the L, has everything you need within a 5 minute walk and is in a great neighbourhood. John, the host, is outstanding. Nothing is too much trouble and he gives some great recommendations of local restaurants/ activities. I would highly recommend this apartment if you are in Chicago - we are sure to be back!
Guest favorite
A long hallway is lined with chalkboard-painted walls, showcasing colorful drawings and notes. Light is provided by ceiling fans and bright fixtures, leading towards an entryway with a glimpse of furniture and natural light coming from an open door.
Private room in East Rogers Park
4.87 out of 5 average rating, 83 reviews

Beautiful condo close to the beach

DihanRating, 5 stars4 months ago
I feel lucky to stay at this place during my 2 month visit to Chicago. Barbara and James were amazing hosts, always caring and making sure their guests feel at home. They were also super helpful about everything a first-time traveller needed to know, from weather to transportation, food to community events. The apartment itself was cozy and lively, way beyond what it seemed on the photos! A variety of apparatus made a seamless transition to life in Chicago. Meanwhile, a Walgreens was within 15 mins walk. A Trader Joe’s and a Target within walking distance. The neighborhood is peaceful and diverse. Nearby, there were top restaurants of Mexican, Peruvian, Vietnamese, Indian, Middle Eastern, Greek, Haiti cuisines, just to name a few. Public transit was extremely convenient to either downtown Chicago or Evanston. Despite the possibilities to adventure, living expenses were easy manageable. Because of Barbara and James, I had an unforgettable and amazing journey at Chicago.
Guest favorite
Condo in Kenwood
4.95 out of 5 average rating, 43 reviews

Beautiful Condo in North Kenwood with Parking

GeoffRating, 5 stars1 month ago
Very nice condominium in a great location. We were attending a trade show at McCormick Place and it was about 10 minutes drive. Plenty of room, well equipped and very comfortable. The massage chair was a nice bonus at the end of a long day! Lisa is very friendly, helpful and always available to help with requests or information. Highly recommended!
Guest favorite
The modern kitchen features stainless steel appliances, an island with circular stone stools, and sleek cabinetry. Pendant lights hang above, illuminating the space, while natural light filters in from the adjacent living area through glass doors.
Private room in West Town
4.89 out of 5 average rating, 260 reviews

Private BR in Chicago - Dwntwn & Fulton Mkt close

JinRating, 5 stars2 weeks ago
I was in Chicago for a conference, and Saurin’s place was a few minutes away from a bus stop to get to the venue. The neighborhood is quiet and off the main road, which has a lot to do. Saurin was an incredibly responsive host and I’m thankful for his friendliness and hospitality.

Quick stats about vacation rentals that are smoking-friendly in Chicago

  • Total rentals

    230 properties

  • Total number of reviews

    9K reviews

  • Family-friendly rentals

    90 properties are a good fit for families

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

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