Smoking-friendly holiday rentals in South Loop

Bronzeville Jazz room. Beautiful, cozy, centered.

Kick back and relax with friends, family, colleagues, in this calm, stylish space. Decorated by a professional interior designer, professional landscaper, to give you a luxurious experience from the moment you step on the property. Stylishly decorated for your comfort and relaxation. 10 mins drive to downtown, 5 mins to university of Chicago, 5 mins to Mccormick place, 5 mins to Chicago white Sox, safe walkable neighborhood for coffee, quick meal, sit down restaurant, art galleries and many more

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.

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.

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

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.

“The Sunflower Suite” 420 Friendly - Free Parking

✨🌻✨Welcome to The Sunflower Suite - Private Apartment. 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 couple, small family or group of friends 🎸LoLLapaLooZa & RIOT Fest’s fans favorite 🍀420 friendly🍀 🚙 FreeParking and own main door access code to check-in at ANY time after 3 p.m. no-hassle check-in guaranteed 🏡 Safe neighborhood with restaurants & stores

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, speakeasy room 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

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."

Pilsen Sweet Life - Near Downtown - McCormick

Experience authentic Pilsen—Chicago’s vibrant, artsy neighborhood/Thalia Hall/Restaurants/Mex Fine Arts Musem. 2 blocks from Train to City Center, Rental Bikes at corner, UIC/Medical Campus 1 Mile North. This modern 2 bed, 1.5 bath home offers the perfect blend of comfort and style just minutes from downtown, Chinatown, and McCormick Place. Enjoy free street parking along Loomis, private park 1 standard vehicle in back. Discover local art, breweries, and dining right outside your door.

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

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!

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