Smoking friendly vacation rentals in South Loop, Chicago

Find and book unique smoking friendly rentals on Airbnb

Top-rated smoking friendly rentals in South Loop, Chicago

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

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Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 6 reviews

Entire Huge 1 BDRM Loft Unit

Newly Rehabbed, Renovated, 1 bedroom Loft style garden unit is available, Unit has a full kitchen with a separate dining room. Unit boasts a huge living room with 13 Ft ceilings, a huge bedroom with a walkin closet and a queen size bed along with a huge dresser. The bathroom has been renovated and the appliances are brand new. Corner Office space within living room along with other features. All Furniture is brand new as the unit has been completely redone for you Plenty of Restaurants around.

Guest favorite

Apartment in Chicago

4.87 out of 5 average rating, 45 reviews

Spectacular Rooftop Getaway in Heart of City

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

Home in Chicago

4.89 out of 5 average rating, 36 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.

Guest favorite

Home in Chicago

4.95 out of 5 average rating, 129 reviews

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 favorite

Apartment in Chicago

5.0 out of 5 average rating, 13 reviews

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.

Superhost

Apartment in Chicago

4.81 out of 5 average rating, 26 reviews

McCormick Place 420 friendly 2brs/parking/sleeps 6

• MESSAGE US for SPECIAL RATES • Steps away from McCormick Place, Wintrust arena and Soldier Field • Michigan Avenue location • 420 friendly unit • Short drive from Millennium Park • 24/7 security surveilled hallways and building • Smart HDTV with Netflix and Roku • 2 Queen size beds + Sofa bed for 2 extra guests • Dedicated High speed Internet • Fully equipped kitchen with complimentary Coffee & Tea • Minutes to all touristic destinations • Optional Parking space for only $30/day

Guest favorite

Guest suite in Chicago

4.91 out of 5 average rating, 74 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 favorite

Guest suite in Chicago

4.95 out of 5 average rating, 120 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

Apartment in Chicago

4.69 out of 5 average rating, 35 reviews

McCormick Place 420 friendly 3Br/2Ba opt Parking

• MESSAGE US for SPECIAL RATES • Smoking inside the unit allowed • State street location • Minutes walk to McCormick Convention Center • Safe building monitored by our Security team • 3 Queen size bedrooms for a comfortable stay for 6 guests • 2 full bathrooms for our guests convenience • Dedicated 250 Mbps Internet • 4K Roku HDTV • Fully equipped kitchen • Minutes to all touristic destinations • Optional Parking space for only $30/day • In-unit washer and dryer

Guest favorite

Apartment in Chicago

4.95 out of 5 average rating, 654 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 favorite

Guest suite in Chicago

4.87 out of 5 average rating, 45 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

Superhost

Loft in Chicago

4.79 out of 5 average rating, 205 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