2. Chicago, Illinois
With lots of dog-friendly beaches along the Lake Michigan coast, Chicago is a great city to enjoy with your furry friend. Chicago is well known for its anti-cruelty campaigns and boasts many pet welcoming venues. Even the famed Chicago White Sox allow dogs into the stadium for special events. There are a handful of designated areas throughout Chicago where dogs are allowed to run off-leash. Some of these sites feature doggie drinking fountains, shy dog corners, pet owner bulletin boards and waste bags.