Smoking-friendly vacation rentals in North Side

The living room features a large area rug with intricate patterns and bright colors, surrounded by plush seating options. A wide television screen is mounted on the wall, and various plants add greenery. Colorful artwork adorns the walls, providing a vibrant atmosphere.

5 out of 5 average rating, 5 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

4.89 out of 5 average rating, 143 reviews

A cozy bedroom is presented with warm wood flooring and soft lighting. A spacious bed is adorned with neutral bedding, complemented by a decorative bench at the foot. A dresser and artwork decorate the walls, while natural light filters in through small windows.

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, 55 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

Superhost

New place to stay

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.

4.85 out of 5 average rating, 20 reviews

Peaceful Zen Flat | 2BR Oasis with Free Parking

Escape to this bright, luxe West Town retreat designed to feel like your own boutique city hideaway. Nestled on a quiet, tree-lined street in the heart of Ukrainian Village, you’re moments from Wicker Park’s top restaurants, coffee shops, nightlife, and shopping — without the noise. Inside, enjoy sun-drenched interiors, calming organic textures, a chef’s kitchen, spa-inspired touches, Smart TVs in every bedroom, in-unit laundry, fast WiFi, and the ultimate Chicago luxury: free onsite parking.

Superhost

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.

Superhost

Home in Chicago

University Gallery - Spacious Home by OPC and DTWN

Welcome to your modern retreat in Woodlawn, University Gallery! Just minutes from the Obama Center, University of Chicago, and vibrant Hyde Park, this spacious 5-bedroom, 3.5-bathroom single-family home is perfect for families or groups. Enjoy the cozy private backyard, ideal for relaxation after exploring the city. With access to downtown Chicago, just 13 minutes away and Northwest, Indiana. Enhance your stay with our hospitality services , tailored to make your experience truly memorable.

Guest suite in Arlington Heights

A bright living space features a spacious sectional sofa accented with blue and white cushions. A round coffee table sits atop a decorative rug. A large clock adorns the wall, while a dining area with a wooden table and chairs is visible in the background.

4.95 out of 5 average rating, 76 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.

4.95 out of 5 average rating, 190 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 living area is presented with a light-colored sectional sofa and a glass coffee table on a colorful area rug. Two bright windows allow natural light, while a ceiling fan enhances airflow. A small table is positioned beside a bookshelf and television.

4.91 out of 5 average rating, 108 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!

A bright living room is illuminated by natural light from large windows. A white sofa is paired with two orange chairs, complemented by vibrant cushions. A coffee table with a striped design sits centrally, surrounded by decorative plants and artwork on the walls.