Smoking-friendly holiday rentals in South Side

4.89 out of 5 average rating, 143 reviews

Guest suite in Chicago

Cozy 1BR + Futon • Deck • Laundry • Private Entry

Located at the geographic center of Chicago with plenty of FREE street parking. The area is very safe and about a 10-min walk to the 35th/Archer Orange Line and just 3 blocks from the Archer bus—both take you downtown within minutes. This lower-level 1BR has a private entrance, spacious queen bedroom, living room with full futon, full kitchen, and private bath. Perfect for solo stays, couples, small families, or work trips. Enjoy your own space with access to a back patio, grill, and laundry.

4.91 out of 5 average rating, 56 reviews

Artist Lofty GAME Garden-Humboldt Park 2BR Cozy

Urban oasis in Humboldt Park, where the local’s live! Lofty, open-concept w/ exposed brick walls, & lower ceilings: • 2BR, 1 Bathroom + futon • Fully equipped kitchen • Private space for late-night chill sessions & good vibes 🌿 • 2.4GHz guest WiFi for emails, & light work • Lush backyard • Free easy street parking 1/2 block away • On-site vending machine & free laundry • Bluetooth Soundbar 🎵🎥 Loud levels at night is not a problem. You will also hear the upstairs neighbors footsteps above.

4.96 out of 5 average rating, 200 reviews

An inviting outdoor patio area features sleek white furniture, including a curved sofa and a coffee table atop a striped rug. A hammock is suspended nearby, surrounded by lush greenery and a wooden fence, with the warm glow of lights illuminating the space.

Home in Chicago

The Chicago River House – GIANT wall projector!

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

5 out of 5 average rating, 5 reviews

Cozy smoking unit Downtown | McCormick | Lakefront

When you step inside this bright South Loop apartment, the city instantly fades behind you. Light filters in through the windows, warming the hardwood floors, and the quiet hum of the space feels like a soft welcome. You breathe deeper. You feel the comfort settle in. This is where your Chicago days begin—and where they gently end. Just minutes from McCormick Place, museums, restaurants, and transit, this home offers the mix of convenience, comfort, and privacy right in the heart of the city.

4.89 out of 5 average rating, 9 reviews

City Retreat

Welcome to your home away from home in the heart of Chicago! This charming, two bedroom home offers a blend of comfort, convenience and accessibility. The vibrant Neighbourhood put you close to local amenities, dining and entertainment. You’ll find excellent restaurant shops, cultural attractions within walking distance. The area is well connected with easy access to public transportation, making it easy to explore what Chicago has to offer. Full cable premium package provided free of charge.

4.83 out of 5 average rating, 36 reviews

The compact kitchen features light gray cabinets and white countertops. Essential appliances include a gas stove, a refrigerator, a microwave, and a coffee maker. A stainless steel sink is positioned near the stove, with kitchen utensils and plants adding functional detail to the space.

Apartment in Thornton

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.

A serene garden space is illuminated by string lights, casting a warm glow over abundant greenery and colorful flowers. Stone paths wind through the lush plants and potted orchids, creating an inviting atmosphere for relaxation and gatherings.

4.95 out of 5 average rating, 744 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. Family friendly with additional kid/baby toys and supplies. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 15 years hosting we still enjoy making our space special…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."

4.95 out of 5 average rating, 191 reviews

A brick bungalow features a welcoming front porch adorned with a US flag. The porch includes a railing and seating area, while flower pots add greenery. Stairs lead up to the front door, which is detailed with a decorative screen.

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

A three-story brick building showcases intricate detailing on its facade. Large windows allow natural light to filter into the spaces inside. A well-manicured bush and symmetrical landscaping frame the entrance, enhancing the welcoming appearance of the property.

4.91 out of 5 average rating, 109 reviews

Cannabis Condo 4BR

Beautiful, spacious apartment is located 10 min from Beach. 10 mins to Hyde Park, (Tiger Woods) Golf Course. 10 mins from Obama Library (coming soon). 10 mins from Museum of Science and Industry. 20 mins from downtown/Soldiers Field (Bears Stadium), Northernly Island concerts, Field Museum, and Shedd Aquarium (beautiful drive down Lakeshore, Metra Electric Line train, or Bus). 15 min from Indiana casino. Ideal for Summer time Chi or Winter snow Chicago!

4.89 out of 5 average rating, 203 reviews

A spacious living area features warm wooden flooring and exposed brick walls. A comfortable sofa is positioned near two elegant table lamps, with a large window providing natural light. A flat-screen TV is mounted on the wall opposite, creating a welcoming atmosphere.

Guest suite in Chicago

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

4.89 out of 5 average rating, 198 reviews

An outdoor patio is illuminated by soft lighting under a protective shelter. Comfortable seating arrangements include folding chairs and metal benches. In the center, a fire pit is surrounded by stones, with flames providing warmth and a calming ambiance during the evening.

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.