This travel spot is featured in our seventh blog series, Sheps Stay. Photo by 2026 Time Out No trip to Chicago, Illinois with your dog is complete without a visit to Montrose Dog Beach, the city's only official off-leash beach. Here, your pup can splash in Lake Michigan, run through the sand, and make new furry friends while you take in stunning views of the Chicago skyline. This one-of-a-kind destination combines the excitement of a big city with the freedom of a lakeside ad