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Smoking-friendly vacation rentals in Cook County

Find and book unique smoking-friendly rentals on Airbnb

Top-rated smoke-friendly accommodations in Cook County

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

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Home in Chicago

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 favourite

Camper/RV in Gary

Horse farm with Miller beach parking.

Insta @rocking_horse_camping_ranch Love horses? Fishing? Mother Nature? We are the closest farm out side of Chicago. A hidden, unique property to escape the city life. We have 3 horses, 4 ponies and 5 goats all are very friendly. We have 20 acres of land you would never know is there! Bird watching? The property is located on Calumet river! Amazing fishing and ponds down the block. BEACH PARKING INCLUDED. A 10 minute drive to private parking 3 blocks from the beach. Perfect for just couples.

Guest favourite

Home in Chicago

Chicago Riverhouse summer on our 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. Amazing chef’s kitchen! 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Chill private patio with illuminating sofa

Guest favourite

Guesthouse in Arlington Heights

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

Rental unit in Chicago

Luxury Villa 10 mins to Downtown

Welcome to the Windy City! La Villita is the gateway to Chicago's vibrant Mexican-American area. Super cozy , modern and centrally located in the heart of Chicago. Close to everything - 5 Star Dining and authentic shops making it easy to plan the perfect Chicago experiences. 15 Minutes to The Loop, Downtown, major event venues (Soldier Field, United Center, McCormick Place) University Of Illinois Chi, Medical District , Chinatown, Little Italy, and many restaurants and popular attractions.

Guest favourite

Campsite in Midlothian

Waverly Woods Outpost: Private Glampsite w Theater

*CALENDAR NOW OPEN FOR LATE JUNE-OCT!!*Unique accommodation offers guests a 'glamping' experience while still affording public transit accessibility into the city of Chicago, & security of being nestled in a residential area. Outdoor movie theater pergola, stock tank pool with deck, firepit, heated outdoor shower, and your choice between one or two 16' bell tents w/ electric, queen beds, additional sleeping mats, & bathroom tents w/ flushing camp toilets. 15 mins from Tinley Concerts!

Guest favourite

Guest suite in Chicago

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

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

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

Rental unit in Chicago

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

Home in Chicago Ridge

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.

Guest favourite

Townhouse in Country Club Hills

Luv Happii House

Truly enjoy home away from home at the Luv Happii House, a Charming, vintage style canna friendly townhouse. Perfect for a weekend getaway, business trip, work from home alternative, content creation, or cozy home base while exploring everything Chicago and the South Suburbs of Chicago have to offer including nearby The Credit Union 1 Amphitheater and Tinley Park Convention Center.

Vacation rentals for every style

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Apartments

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Houses

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Hotels

Stylish accommodations and amenities

Popular amenities for Cook County smoke-friendly accommodations

Free parking on premises

Air conditioning

Smoking-friendly apartment rentals

Guest favourite

Rental unit in Cicero

Modern Cicero apartment

Guest favourite

Rental unit in Chicago

420 at Cheltenham 4BR

Guest favourite

Rental unit in Oak Park

Historic Hotspot Apartment

Rental unit in Chicago

McCormick Place 420 friendly 3Br/2Ba opt Parking

Guest favourite

Rental unit in Chicago

Spectacular Rooftop Getaway in Heart of City

Rental unit in Chicago

“The Sunflower Suite” 420 Friendly - Free Parking

Rental unit in Chicago

Entire Huge 1 BDRM Loft Unit

Guest favourite

Rental unit in Downers Grove

Pet friendly private studio apartment

Smoke-friendly house rentals

Guest favourite

Home in Chicago

Cheerful 2 Bedroom Residential Home with Finished Basement, full kitchen and Dining Room. 2 Residential Parking passes per 24 hour stay!

Home in Chicago

1501HOME | West Town Single Family Home + Garage

Guest favourite

Home in Matteson

"Just Like Home"

Guest favourite

Home in Carol Stream

LAKE HOUSE HotTub/Kayak/Billiards/Pets/Fenced Yard

Home in Chicago

Stunning 4 BR Home * Chicago * Centrally Located

Guest favourite

Home in Chicago

420 lux and huge 1 bedroom that will WOW you

Home in Lemont

Nature retreat hide n seek private suite/ house

Home in Richton Park

Beautiful Suburban Home 30 mins from downtown!

Smoke-friendly condo rentals

Guest favourite

Condo in Chicago

Beautiful Condo in North Kenwood with Parking

Guest favourite

Condo in Chicago

3 Story Luxury Condo with Massive Roof-top Deck

Guest favourite

Condo in Chicago

Where you want to BE! Stylish, Comfy, Luxe

Guest favourite

Private room in Chicago

Private BR in Condo close to Chicago Dwtwn!

Guest favourite

Private room in Chicago

Beautiful condo close to the beach

Guest favourite

Private room in Chicago

Private BR in Chicago - Dwntwn & Fulton Mkt close

Private room in Chicago

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

Destinations to explore