The Insider's Guide to Chicago

Situated on the shores of beautiful Lake Michigan, Chicago is the premier metropolitan destination in the Midwest. World-class restaurants, high-end shopping, lively nightlife, and globally recognized art and architecture make the Windy City a desirable weekend destination for a wide variety of travel personalities. With long winters that can border on brutal, spring, summer, and fall are the best times to see the city, so if it’s on your list for an upcoming trip, keep scrolling for our picks of where to eat, drink, stay, and play.