Smoking-friendly vacation rentals in North Side

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

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.

“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

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.

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."

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.

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

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.