One of the "13 most pet-friendly hotels in the country"- Time Out

No need to leave part of the family behind. Well-behaved dogs of all shapes and sizes are always welcome at                       The Guesthouse Hotel and there is never an extra charge! From treats upon arrival to belly rubs during their stay, your pup will receive Very Important Pooch service from our team of dog-lovers! We offer complimentary beds, food & water bowls and baggies upon request. 


  • Urban Pooch Canine Life Center:                                                                                                                                           4501 N. Ravenswood Ave (773) 942-6445                                                                                                                           Visit our friend Berwyn the Welsh Terrier for yummy treats and fuzzy toys. Great place to play, shop, and even get a bath!  
  • Montrose Dog Beach:                                                                                                                                                       Lawrence Ave at Lake Michigan just 1.5 miles away                                                                                                                    Just named the best dog beach in the country! Fenced in on three sides so your pooch can frolic in the lake safely!           
  • Puptown Dog Run:                                                                                                                                                                    4921 N. Marine Dr.                                                                                                                                                                 Large, fully enclosed neighborhood dog run close to the lake- even has a water fountain for pups and people!


  • The Collection at The Guesthouse Hotel                                                                                                                               Right here in the lobby featuring Chicago flag bowls, collars and leads                   
  • Jameson Loves Danger                                                                                                                                                             5208 N. Clark St. (773) 754-8816                                                                                                                                        Locally owned by J and Grace, this store is just up the street and full of fun toys, warm coats, and doggy accessories.


  • Clark Street:                                                                                                                                                                                 Take a stroll into the heart of Andersonville and get treats along the way from our pet-friendly neighbors! Stop in Milk Handmade and you just might meet our friend Sauvie the Greyhound. Keep your eye out for the Fido to Go "gourmutt" food truck which frequents our neighborhood on summer weekends. And pooches are welcome at most neighborhood sidewalk cafes, too!
  • Mercury's Canine Cruise:    Seasonal                                                                                                                                             It might be all fresh water in these parts, but this tour is sure to bring out your inner salty-dog! Everyone's tail will be wagging on this fun city boat tour. Watch Here. Reservations required!