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Smoking-friendly holiday rentals in South Side

Find and book unique smoking-friendly rentals on Airbnb

Top-Rated Smoke-Friendly Accommodation in South Side

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

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

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

Rental unit in Chicago

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 Chi on Lake Shore Drive Beaches. Lollapalooza. Riotfest. Bears during football season. Winter wonder festival. Great food. Great for larger groups visiting looking to divide costs. Obama Library, golf course, Reggies on the Beach, Soldiers Field, Shedd Aquarium, Field Museum, Museum of Science & Industry are within 20 minutes.

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!

This home offers you 2 Bedrooms, 2 full bathrooms, finished basement, full kitchen with microwave! Dining area and entertainment in a full finished basement with a restroom! This is your place to stay on quiet block, less than a half block to transportation. 1 Bus ride to Downtown Chicago and a short 15 minute ride to the Loop and Museum's. Centrally located, less than a minute drive to the Dan Ryan expressway. Clean, comfortable and spacious! Dining Room seats up to 7 people!

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 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

Rental unit in Chicago

McCormick Place 420 friendly 2BR/parking/sleeps 6

• 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 • 2 Queen size bedrooms + Queen size Sofa bed for a comfortable stay for up to 6 guests • Dedicated fast Internet • 4K Roku 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.

Holiday rentals for every style

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Apartments

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for South Side Smoke-Friendly Accommodation

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

Spectacular Rooftop Getaway in Heart of City

Guest favourite

Rental unit in Calumet City

Welcome to True Blue.

Guest favourite

Rental unit in Oak Park

Historic Hotspot Apartment

Rental unit in Chicago

“The Sunflower Suite” 420 Friendly - Free Parking

Rental unit in Chicago

Entire Huge 1 BDRM Loft Unit

Rental unit in Chicago

Homey, clean, & private 1 bed, 15min to city

Guest favourite

Rental unit in Downers Grove

Pet friendly private studio apartment

Smoke-Friendly Holiday Houses

Home in Chicago

1501HOME | West Town Single Family Home + Garage

Home in Chicago

Stunning 4 BR Home * Chicago * Centrally Located

Home in Monee

The Clubhouse

Guest favourite

Home in Matteson

"Just Like Home"

Guest favourite

Home in Carol Stream

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

Guest favourite

Home in Chicago

420 lux and huge 1 bedroom that will WOW you

Home in Country Club Hills

Entire suburban home 30 mins from downtown Chicago

Home in Lemont

Nature retreat hide n seek private suite/ house

Smoke-Friendly Holiday Condos

Guest favourite

Condo in Chicago

3 Story Luxury Condo with Massive Roof-top Deck

Guest favourite

Condo in Chicago

Beautiful Condo in North Kenwood with Parking

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