
Smoking friendly holiday rentals in Chicago
Find and book unique smoke-friendly rentals on Airbnb
Top-rated smoke-friendly rentals in Chicago
Guests agree: these smoking-friendly rentals are highly rated for location, cleanliness and more.

Chicago River House -BBQ Oasis now open!
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

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 Chicago Lake Shore Drive Beaches. Lollapalooza. Chicago Riverwalk. Concerts at Soldiers Field-Bears. Winter wonder festival. The Bean. Great for larger groups visiting looking to divide costs. Obama Library, Southshore golf course, Reggies on the Beach, Shedd Aquarium, Field Museum, Museum of Science & Industry are all within 20 minutes.

Your quiet south suburban oasis
NO PARTIES! Relax and enjoy yourself in this south suburban duplex located in a safe and quiet location! We offer the entire unit so you don’t have to worry about sharing. 1 bedroom but the living room is spacious enough for an air mattress (must bring own). Large yard for you and your family to enjoy outdoor activities! Park less than 1 block away. 4 blocks from the famous rock quarry of Thornton. New casino less than 2 miles away. Bar right across the street! Animals allowed if trained.

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.

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.

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

Chicago's Finest Airbnb/airport shuttle/ tours.
Unwind in a spacious, beautifully designed home with a private 420-friendly backyard lounge made for fun and comfort. Featuring a modern kitchen, 85" TV, fireplace, jacuzzi tub, and remote-controlled bedroom AC, this stylish property is just minutes from downtown, university of Chicago hospital and the beach. The backyard includes a large gazebo, luxurious patio furniture, pool table, card table, and TV—your perfect spot to relax and unwind.

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."

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

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

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.

Heart of Logan Square easily Walk to Dining & Fun
Experience the heart of Logan Square! Stylish 2BR/1BA in a multi-unit family building. Walk to Armitage Ave’s top spots—Giant, Moonlighter, Carson’s Chicken, Scofflaw, and more! Close to Palmer Square, 606 trail, Blue Line, Bucktown, and Wicker Park. Enjoy a fully equipped kitchen, 70” Smart TV, washer/dryer, easy self-check-in, and free street parking. No parties per Chicago regulations. Book your stay today!
Popular amenities for smoke-friendly rentals in Chicago
Smoke-friendly flat rentals

The Green Lantern

Studio Apartment in Nature Sancturary

Pet friendly private studio apartment in a home

The Hype Loft | Parking • Walk to United Center

Modern 2BR in Chicago’s South Loop | 420 Friendly

Stylish, Centrally Located, 420-Friendly Duplex!

The Courtyard Escape

420 friendly apt with 2 queens,1 full,1 twin bed
Smoke-friendly house rentals

Music Hot Spot Three Level Home

Spacious Designer Oasis: Game Room - Yard - Garage

Nature retreat hide n seek private suite/ house

Master bedroom suite with attached bathroom

home in plainfield illinois

A Cozy Room for Two in Vibrant Logan Square

fun place for family and friends

Rejuvenate: 4BR, fenced yard
Smoke-friendly apartment rentals

Private BR in Condo close to Chicago Dwtwn!

Urban Oasis: South Shore Chicago

Where you want to BE! Stylish, Comfy, Luxe

Private BR in Chicago - Dwntwn & Fulton Mkt close
Quick stats about holiday rentals that are smoking-friendly in Chicago
Total holiday rentals
Explore 220 holiday rentals in Chicago
Nightly prices starting at
Chicago holiday rentals start at € 9 per night before taxes and fees
Verified guest reviews
Over 9,240 verified reviews to help you choose
Family-friendly holiday rentals
110 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 80 rentals that welcome pets
Holiday rentals with a pool
10 properties feature pools
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Wifi availability
210 of Chicago holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chicago rentals
4.6 Average rating
Chicago stays receive an average rating of 4.6 out of 5 from guests
Nearby attractions
Chicago’s top spots include Millennium Park, Wrigley Field and Lincoln Park
Destinations to explore
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- Fitness-friendly rentals Chicago
- Rentals with a sauna Chicago
- Lakehouse rentals Chicago
- Family-friendly rentals Chicago
- Rentals with a patio Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Boutique hotel rentals Chicago
- Waterfront rentals Chicago
- Rentals with lake access Chicago
- Pet-friendly rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with pools Chicago
- Loft rentals Chicago
- Ski-in/ski-out rentals Chicago
- Mansion rentals Chicago
- Rentals with a balcony Chicago
- Townhouse rentals Chicago
- Beachfront rentals Chicago
- Serviced apartment rentals Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- House rentals Chicago
- Bed and breakfasts Chicago
- Flat rentals Chicago
- Private suite rentals Chicago
- Rentals with an accessible-height bed Chicago
- Rentals with beach access Chicago
- Rentals with a fireplace Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Rentals with an EV charger Chicago
- Smoking-friendly rentals Cook County
- Smoking-friendly rentals Illinois
- Smoking-friendly rentals United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo
- The Beverly Country Club
- Raging Waves Waterpark
- The 606
- Things to do Chicago
- Food and drink Chicago
- Art and culture Chicago
- Sports activities Chicago
- Sightseeing Chicago
- Nature and outdoors Chicago
- Entertainment Chicago
- Tours Chicago
- Things to do Cook County
- Food and drink Cook County
- Sightseeing Cook County
- Entertainment Cook County
- Sports activities Cook County
- Tours Cook County
- Art and culture Cook County
- Nature and outdoors Cook County
- Things to do Illinois
- Sports activities Illinois
- Sightseeing Illinois
- Nature and outdoors Illinois
- Art and culture Illinois
- Food and drink Illinois
- Tours Illinois
- Things to do United States
- Sightseeing United States
- Sports activities United States
- Entertainment United States
- Nature and outdoors United States
- Art and culture United States
- Wellness United States
- Food and drink United States
- Tours United States