Smoking-friendly vacation rentals in Downtown Chicago

5 out of 5 average rating, 3 reviews

“Dream Catcher Suite” Gorgeous Multicultural Home

✨🦚✨ Welcome to The Dream Catcher Suite - private unit 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 family or a group of friends getaway! Enjoy our Gorgeous Multicultural Home and a nice 420 experience. FreeParking & own main door access code to check-in at ANY time after 3 p.m. no-hassle check-in guaranteed Safe & nice neighborhood with restaurants & stores

4.85 out of 5 average rating, 53 reviews

Rooftop HotTub As Seen On "Married At First Sight"

This Penthouse is the most unique spot you’ll find near downtown with 2 enormous rooftop decks that offer a fully private 6-person hot tub & the best views of the Chicago skyline! The home is in the posh Bridgeport neighborhood where you can walk to White Sox stadium in less than 5 minutes, or enjoy being immersed in the rich culture of the area which is family-friendly, yet packed with bars & restaurants for daytime & nightlife enjoyment! Once you arrive, we guarantee you won't want to leave!

4.74 out of 5 average rating, 38 reviews

Condo in Chicago

Wicker Park Loft Style Apartment

Experience the best of Chicago with a stylish stay at our centrally-located home in the heart of Wicker Park! This space is packed with great amenities & just steps from the city’s top spots. Kick back & relax as you enjoy 1 of our three Smart TVs, play a round of pool, challenge each other to board games, or try your hand at darts. We’ve stocked the place with all the essentials. Feel at home & enjoy a complimentary welcome basket of snacks to start your stay off right. We cant wait to host you

4.96 out of 5 average rating, 170 reviews

Home in Chicago

Chicago River House -BBQ Oasis now open!

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

4.95 out of 5 average rating, 106 reviews

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.

4.88 out of 5 average rating, 8 reviews

Home in Oak Park

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!

Apartment in Calumet City

4.77 out of 5 average rating, 26 reviews

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….

4.82 out of 5 average rating, 73 reviews

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, 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

4.89 out of 5 average rating, 103 reviews

Guest suite in Chicago

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.

4.94 out of 5 average rating, 159 reviews

Guest suite in Chicago

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

5 out of 5 average rating, 12 reviews

Home in Romeoville

Rejuvenate: 4BR, fenced yard

Welcome to our cozy Romeoville retreat! This spacious one-level home offers plenty of room to relax and unwind. Enjoy cooking in the fully stocked kitchen, complete with all the essentials for your favorite meals. Step outside to the fully fenced backyard, perfect for outdoor dining, lounging, or letting kids and pets play safely. Whether you’re here for a weekend getaway or an extended stay, this home offers all the comfort and convenience you need.