Illinois

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

Galena, Illinois. Sounds cool, right? One of the biggest things about this town is its connection to Ulysses S. Grant. Sure, he was born in Ohio, but in 1860 he moved to Galena with his wife Julia and their kids. Luie Boone thinks that’s a solid life choice. Back then, Grant worked quietly in his father’s leather goods store. Luie likes to picture him sweeping the floor and daydreaming about, you know, saving the Union. No big deal.

Luie Boone wonders about lakes a whole lot. He reckons that lakes are one of the best places in the whole entire world. He loves sprinting off docks and cannonballing into the water, creating the biggest splash ever known to pooch. A vacation to Wonder Lake, Illinois, sounds like the perfect place to break his world record cannonball splash. And guess what? His hoomans crafted a travel guide to just that place.