Smoking-friendly holiday rentals in Chicago

420-Friendly 2BR Retreat • Private Yard Near DT

Welcome to Chicago’s Finest Getaway. A stylish and relaxing retreat just 10–15 minutes from downtown. Enjoy two queen bedrooms, a cozy living room with an 85” smart TV and fireplace, a modern kitchen, and a jacuzzi tub. Step into your private 420-friendly backyard lounge with a gazebo, luxury seating, pool table, and outdoor TV. Perfect for families, couples, and weekend explorers looking for comfort, privacy, and easy access to Chicago’s top attractions.Optional airport transportation available

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.

The Chicago River House – City Escape Meets Nature

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

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 Chicago Lake Shore Drive Beaches. Lollapalooza. Chicago Riverwalk. Concerts at Soldiers Field-Bears. Winter wonder festival. The Bean. Great for larger groups visiting looking to divide costs. Obama Library, Southshore golf course, Reggies on the Beach, Shedd Aquarium, Field Museum, Museum of Science & Industry are all within 20 minutes.

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.

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

Winter Escape|Near DePaul|Free parking+AC/Heat

1 king, 1 queen, and 1 airbed Self Check-in 24/7 support Super host property Central AC and Heat Fully stocked kitchen Bathroom w/ fresh towels & essentials 1 FREE parking spot (a rare find in the city!) This charming and fully equipped 2-bedroom apartment is perfect for couples, families with kids, business travelers, or university visitors. Located just steps from DePaul University, enjoy the walkable lifestyle of one of Chicago's most vibrant neighborhoods.

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."

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

Quirky Bucktown Loft w/ Parking No Parties

Located on a peaceful treelined street in energetic, fashionable Bucktown with upscale amenities at your fingertips. This unique penthouse/loft apartment has its share of quirks that come with being a 125-year-old building yet its unique vintage comfort, eclectic furnishings and modern necessities come together to make your time in the city relaxing and unforgettable. This is a legally licensed Chicago vacation rental R22000079930

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.