Smoking friendly holiday rentals in West Side

An outdoor patio area features a long wooden table surrounded by eight light-toned chairs. Potted plants add greenery, and a bar area with stools can be seen in the background. A blue umbrella provides shade, enhancing the inviting setting.

Home in Berwyn

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

4.9 out of 5 average rating, 42 reviews

A comfortable living area features a spacious gray sectional sofa adorned with decorative pillows. A small coffee table sits atop a colorful area rug, and artwork is displayed on the wall. Natural light enhances the calm atmosphere of the space.

Flat in Calumet City

Welcome to True Blue.

Relax with the whole family at this peaceful place to stay. A stylish, great work space, with great dining and entertainment nearby. True Blue is located in the heart of everything, 15 minutes away from downtown Chicago 20 minutes away from Joliet. Right next door to northwest Indiana. Come relax and enjoy this amazing home away from home smoking is allowed inside of home. Please no large parties or gatherings or loud music there is a 500 dollar fee smoking is allowed inside and outside of home.

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.

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.

5 out of 5 average rating, 13 reviews

“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

4.84 out of 5 average rating, 86 reviews

A three-story home is shown with a light-colored exterior and blue accents. A staircase leads up to a covered entryway. Surrounding space includes a driveway for parking and neighboring buildings, along with a well-maintained yard featuring colorful shrubbery.

Home in Chicago

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

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.

4.88 out of 5 average rating, 111 reviews

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 💖🏡

4.86 out of 5 average rating, 152 reviews

Flat in Cicero

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

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.

4.95 out of 5 average rating, 744 reviews

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."