You’ve no doubt heard all the typical stories about Chicago being the city of big shoulders, how cold it gets in the winter, and deep-dish pizza; but there’s so much more to this truly great American city.

Yes, Chicago is still a world-class sports town with equally great hot dogs. But in the last decade, thanks to a cultural and tourist boom, it’s become so much more, a city with grand architecture, entertainment, museums, some of the best sports teams in the country, enough room to walk, run, and bike, and one of the best food scenes in America. Unlike New York City, you won’t bump into bags of garbage thrown out onto the sidewalks, and as the capital of the Midwest, locals are more than willing to show you a good time. Just be warned: you’re probably going to eat and drink a lot, so make sure to plan some time to hit the gym in your hotel or skip using the Uber once or twice and just walk.


Chicago is a drinking city, and has no shortage of places like Delilah’s or Revolution Brewery to get your fill of whiskey or beer, but for something a little different, Three Dots and a Dash has brought a retro South Pacific feel to the notoriously cold city, serving up Tiki classics like the Painkiller, and the scotch-laced Polynesian Pearl Diver, along with a changing menu featuring some of the most creative cocktails anywhere in the country.