Smoking-friendly vacation rentals in Chicago

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

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 Unit +Kitchen & DW Parking - Quiet Area

Description: House: Private BASEMENT Apartment with two spacious bedrooms, equipped kitchen, bathroom, and its own entrance and parking through the driveway. Neighborhood: Located in Alsip/Chicago, on a quiet cul‑de‑sac, 5 minutes from I‑294 and 10 minutes from I‑57, 30 minutes from Downtown. Peaceful, family‑friendly area. Parking: Available in the driveway or on the street. (see photos) Note: We live in the unit upstairs. Rules: One small dog allowed. No parties. No smoking inside.

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.

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

The Green Lantern

Relax and unwind with the family or friends at this peaceful place. A stylish 2 bedroom 1 bathroom home that you 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. This home allow’s smoking inside…

Cheerful 2 bedroom sunny single family home

Relax in a sunny single family home in the suburbs of Chicago with access to a large kitchen, dining room and living room. On-site Wi-Fi available and carport parking on the premises. RULES: * No overnight guests or reservation will be canceled) * No parties or reservation will be canceled immediately * No smoking inside of the house * All trash should be thrown in designated trash cans * Must state if you’re bringing a pet or reservation can be canceled

The Queen and Kingdom

The home is new remodeled with 3 bedrooms and 2 baths. Located in a pleasant, clean and quiet neighborhood. Less than a half of a mile from the new Windcreek casino on Halsted. Its within walking distance from all retail stores, bars, food restaurants and gas stations. The home has a smoking room for the guest that smokes with parking on the premises. Also available is renting a 2022 slingshot is an option with the home for an additional fee.

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.

Loft Style Private Apt 4 (1 Room- 420 Friendly)

Please do not book unless you read the entire listing, including all house rules & amenities. No refunds will be given if you book without first reading the house rules Near Loyola University. 420 friendly environment. No Cleaning Fee, Full Kitchen, Living Room, 1 Shared Bathroom, Internet, Heat, Air Conditioning Redline, CTA, Beach, Groceries, Gyms, Multiple Bars & Diverse Cuisine within 5-15 min walking

Entire suburban home 30 mins from downtown Chicago

Bring the whole family to this great place with lots of room for fun. Full house in quiet suburb with free garage access, driveway, gated backyard, patio, tvs in all bedrooms, and 30 mins from downtown Chicago! Bedroom 1 has 1 queen size bed. Bedroom 2 has 2 full size beds. Bedroom 3 has 2 twin size beds. Bedroom 4 has 1 queen size bed. House is near many restaurants, grocery stores, and gas stations.

Luv Happii House

Truly enjoy home away from home at the Luv Happii House, a Charming, vintage style canna friendly townhouse. Perfect for a weekend getaway, business trip, work from home alternative, content creation, or cozy home base while exploring everything Chicago and the South Suburbs of Chicago have to offer including nearby The Credit Union 1 Amphitheater and Tinley Park Convention Center.