Smoking friendly holiday rentals in South Loop, Chicago

Find and book unique smoke-friendly rentals on Airbnb

Top-rated smoke-friendly rentals in South Loop, Chicago

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

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Superhost

Flat in Portage Park

5 out of 5 average rating, 3 reviews

“Dream Catcher Suite” Gorgeous Multicultural Home

✨🦚✨ Welcome to The Dream Catcher Suite - private unit Thank you for selecting our place for your upcoming stay. We are excited to have you. Take a moment to see what's in store for you during your time on property: This is perfect for a family or a group of friends getaway! Enjoy our Gorgeous Multicultural Home and a nice 420 experience. FreeParking & own main door access code to check-in at ANY time after 3 p.m. no-hassle check-in guaranteed Safe & nice neighborhood with restaurants & stores

Superhost

Flat in Chicago

4.85 out of 5 average rating, 53 reviews

Rooftop HotTub As Seen On "Married At First Sight"

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!

Superhost

Apartment in Wicker Park

4.72 out of 5 average rating, 36 reviews

Wicker Park Loft Style Apartment

Experience the best of Chicago with a stylish stay at our centrally-located home in the heart of Wicker Park! This space is packed with great amenities & just steps from the city’s top spots. Kick back & relax as you enjoy 1 of our three Smart TVs, play a round of pool, challenge each other to board games, or try your hand at darts. We’ve stocked the place with all the essentials. Feel at home & enjoy a complimentary welcome basket of snacks to start your stay off right. We cant wait to host you

Guest favourite

Home in North Park

4.96 out of 5 average rating, 168 reviews

Chicago River House -Glowing Sofa Oasis

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

Guest favourite

Flat in South Shore

4.95 out of 5 average rating, 105 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 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.

Guest favourite

Guest suite in Arlington Heights

4.94 out of 5 average rating, 47 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.

Superhost

Flat in Calumet City

4.77 out of 5 average rating, 26 reviews

The Green Lantern

Relax and unwind with the family or friends at this peaceful place. A stylish 2 bedroom 1 bathroom home that has great work space with a warm inviting kitchen cozy bedrooms relaxing bathroom and unwinding living room. There is also great dining and entertainment nearby. The Green Lantern is located in the heart of everything, 25 minutes away from downtown Chicago, 30 minutes away from Joliet. Right next door to northwest Indiana. Come relax and enjoy this amazing home away from home…

Superhost

Home in Austin

4.82 out of 5 average rating, 71 reviews

Stunning 4 BR Home * Near many Chicago Landmarks

Stunning 4 BR Home * Chicago * Centrally Located This is the perfect home for a large group traveling to Chicago. With 3 levels of living space, 2 full bathrooms, central air and heat, parking, and a private yard, you can enjoy the company of your friends and family without giving up the comforts of home. Near the expressway. Downtown 7 mi Midway Airport 6 mi Ohare Airport 19 mi Chicago Bulls & Black Hawks 4 mi White Sox Stadium 9 mi Cubs Stadium 12 mi Mccormick Place

Guest favourite

Guest suite in McKinley Park

4.89 out of 5 average rating, 102 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 favourite

Guest suite in Portage Park

4.94 out of 5 average rating, 157 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

Flat in East Pilsen

4.89 out of 5 average rating, 27 reviews

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

Immerse yourself in East Pilsen, Chicago's most artistic neighborhood, where culture meets convenience. This luxe studio is just minutes from downtown, Chinatown, and a 7-minute walk to Radius Chicago. Surrounded by vibrant restaurants, breweries, bars, and art galleries, it's perfect for travelers seeking a stylish retreat with free parking. Enjoy the best of the city next door to downtown—without the noise. Send me a message if you have any questions!

Guest favourite

Flat in Logan Square

4.95 out of 5 average rating, 692 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."