Smoking-friendly holiday rentals in Portage Park

Music Hot Spot Three Level Home

Multi level option; 5 Beds & 3 full Baths, each level. High Speed Fiber Wifi. Walk to music venues; Friendly Tap/Coffee. Crawl to Fitzgerald's, well-known music venue. Multiple restaurants & shops: Walgreen's, CVS and Grocery. Few blocks to the CTA Blue line & 7 blks CTA Green/Pink. Nature park, zoo, mtn bike, trail run, fishing. 15 min from West Loop, public pool, tennis, Zen garden, patio, grills, smokers, fire pit, indoor bar, speak easy, music recording studio w/soundguy. 30yrs + to stay

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.

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

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 3BR 420-Friendly | Soldier Field & McCormick

Welcome and Experience the heart of Chicago from this stylish 3-bedroom, 2-bathroom loft located on iconic South Michigan Avenue! 🌆 Just steps from McCormick Place, Wintrust Arena, and Soldier Field, this 420-friendly unit offers modern comfort, downtown convenience, and plenty of space for up to 8 guests. Whether you're traveling for a convention, vacation, or work trip — this is your perfect city base. Ready to book your South Loop stay? 🌆✨ Click Reserve and make yourself at home 💖🏡

Modern Cicero apartment

located near Midway Airport, just a 11-minute drive away. Situated in Cicero, IL, the neighborhood exudes a peaceful ambiance, complemented by friendly neighbors. Enjoy the convenience of complimentary street parking, well-equipped kitchen, great appliances. The bathtub features a jacuzzi for added relaxation. Additionally, there’s a shared backyard that can be utilized.Our goal is to ensure a comfortable and enjoyable stay, allowing you to fully immerse yourself in the local experience

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!

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

Spacious King 1BD Top Floor Walkable Edgewater

Revive your soul in this Edgewater Oasis Discover this sun-drenched 1-bedroom retreat on a quiet, tree-lined street in Chicago's historic Edgewater Glen. With 1,250+ sq ft of spacious living, soaring ceilings, easy street parking, and rare outdoor space, this top-floor apartment is your perfect home base for exploring Chicago—or simply unwinding in style. Also available in a 3-bedroom configuration as well