Smoking friendly holiday rentals in South Loop

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.

Spacious Designer Oasis: Game Room - Yard - Garage

Step into the spacious 5BR 3BA designer getaway in the friendly Oak Park area, just 10 minutes to downtown Chicago via the I-290 and the nearby Blue Line. It promises a relaxing retreat just a stone's throw away from restaurants, shops, exciting attractions, and landmarks. The luxurious design and a rich amenity list will leave you in awe. ✔ 5 Comfortable BRs ✔ Open Design Living ✔ Full Kitchen ✔ Game Room ✔ Fenced Backyard ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Garage Parking Learn more below!

The Green Lantern

Relax and unwind with the family or friends at this peaceful place. A stylish 2 bedroom 1 bathroom home that has great work space with a warm inviting kitchen cozy bedrooms relaxing bathroom and unwinding living room. There is also great dining and entertainment nearby. The Green Lantern is located in the heart of everything, 25 minutes away from downtown Chicago, 30 minutes away from Joliet. Right next door to northwest Indiana. Come relax and enjoy this amazing home away from home..

1 bed apartment + futon room bridgeport

Located at the geographic center of Chicago! Plenty of free street parking. Very safe and ~10 min walk to the 35th Orange line and 3 blocks from the Archer bus, both go directly downtown within minutes. Brand new lower level construction unit. Comfortable spacious rooms to relax in. Closet in both rooms for your use while here. The apartment has a separate entrance, bathroom, kitchen, dining space. Enjoy your own private space in Chicago with a back patio, grill, and laundry.

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

420-Friendly 3BR Oasis Near UIC, McCormick Place

🌟 Welcome to The State Suite — Premier Downtown Chicago Stay! 🌟 📩 MESSAGE US for SPECIAL RATES! 🚬 Smoking allowed inside 📍 Prime State Street location 🚶‍♂️ Minutes walk to McCormick Convention Center 🔒 Safe building with 24/7 security 🛏️ 3 Queen bedrooms (sleeps 6) 🛁 2 full bathrooms ⚡ Dedicated 250 Mbps internet 📺 4K Roku HDTV 🍳 Fully equipped kitchen 🚗 Optional parking $30/day 🧺 In-unit washer & dryer 🚶‍♂️ Close to all top Chicago attractions!

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.