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Smoking friendly vacation rentals in Cook County

Find and book unique smoking friendly rentals on Airbnb

Top-rated smoking friendly rentals in Cook County

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

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Rental unit in Chicago

4.85 out of 5 average rating, 53 reviews

Private Rooftop Views from Penthouse Suite

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!

Home in Chicago

4.96 out of 5 average rating, 152 reviews

Chicago River House -Large modern home

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

Home in Chicago

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.

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.

Guesthouse in Arlington Heights

4.95 out of 5 average rating, 41 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 suite in Chicago

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 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

Rental unit in Chicago

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 suite in Chicago

4.9 out of 5 average rating, 86 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

Loft in Chicago

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

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.

Rental unit 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! 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.

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Popular amenities for Cook County smoking friendly rentals

Free parking on premises

Air conditioning

Smoking friendly apartment rentals

Rental unit in Thornton

5 out of 5 average rating, 7 reviews

Your quiet south suburban oasis

Rental unit in Chicago

5 out of 5 average rating, 15 reviews

Hypebeast Experience 1 BED, 1 BA Loft

Rental unit in Chicago

4.83 out of 5 average rating, 12 reviews

Luxury East Pilsen Studio with Cal King Bed for 2

Rental unit in Chicago

4.95 out of 5 average rating, 98 reviews

420 at Cheltenham 4BR

Rental unit in Chicago

4.83 out of 5 average rating, 114 reviews

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

Rental unit in Chicago

4.64 out of 5 average rating, 74 reviews

McCormick Place 420 friendly 2BR/parking/sleeps 6

Rental unit in Chicago

4.71 out of 5 average rating, 123 reviews

Beautiful 3 Bed 1 Bath! Free parking in Logan Sq!

Rental unit in Chicago

4.52 out of 5 average rating, 31 reviews

HUGE Fully Loaded 1 BDRM Loft Oasis

Smoking friendly house rentals

Home in Lemont

4.64 out of 5 average rating, 44 reviews

Nature retreat hide n seek private suite/ house

Home in Gary

4.86 out of 5 average rating, 14 reviews

The Blue House: Family Retreat

Home in Romeoville

4.6 out of 5 average rating, 10 reviews

Rejuvenate: 4BR, fenced yard

Home in Chicago

5 out of 5 average rating, 6 reviews

Modern Single-Family Home w/outdoor space + garage

Home in Richton Park

4.56 out of 5 average rating, 9 reviews

Spacious Split-Level Home 30 mins From Downtown!

Home in Calumet City

5 out of 5 average rating, 3 reviews

Cozy Retreat in Calumet City

Home in Matteson

4.69 out of 5 average rating, 61 reviews

"Just Like Home"

Home in Chicago

4.57 out of 5 average rating, 23 reviews

Cheerful 4 bedroom, 3 bathroom spacious home

Smoking friendly condo rentals

Private room in Chicago

4.88 out of 5 average rating, 286 reviews

Private BR in Condo close to Chicago Dwtwn!

Condo in Chicago

4.83 out of 5 average rating, 24 reviews

3 Story Luxury Condo with Massive Roof-top Deck

Private room in Chicago

4.8 out of 5 average rating, 80 reviews

Master BR w/ensuite (600 Sq Ft.) in Chicago Condo

Private room in Chicago

4.86 out of 5 average rating, 81 reviews

Beautiful condo close to the beach

Condo in Chicago

4.97 out of 5 average rating, 39 reviews

Beautiful Condo in North Kenwood with Parking

Condo in Chicago

4.83 out of 5 average rating, 24 reviews

Wicker Park Loft Style Apartment

Private room in Evanston

5 out of 5 average rating, 15 reviews

Two Private Floors With a Lock & Private Deck

Condo in Chicago

5 out of 5 average rating, 55 reviews

Where you want to BE! Stylish, Comfy, Luxe

Destinations to explore