Chicago Cubs

A Wrigley Field weekend sounds simple enough — fly in, see the game, fly out. But Chicago has a way of expanding your plans, and honestly you should let it. This is four days done right: an architecture cruise, a gangster bus tour, the best underground whiskey bar you’ve never heard of, deep dish with unreasonable amounts of garlic, and yes, a Cubs game at one of the most iconic ballparks in the country.