Why you should travel to Chicago right now

In the ’20s, Chicago gangsters like Al Capone were known to frequent the Green Mill, but ever since Prohibition, the club has garnered a reputation for hosting live jazz. The music typically goes until 1am (later on the weekends) and the lineup of performers includes B-3 organ players, jazz vocalists and classic big bands. Order a cocktail and settle in for a late night.

You’ve probably heard about the city’s fabled culinary delicacies, like the Chicago-style hot dog, deep dish pizza and jus-soaked Italian beef. You can sample all of those dishes (and many, many more) at Time Out Market Chicago in Fulton Market. The 50,000-square-foot destination is home to 18 of Chicago’s best chefs, who serve everything from elegant pastries and addictive dumplings to stacked burgers and grilled oysters. We even tapped some of the top bartenders in town to share their favorite recipes at our bars. Speaking of, no trip is complete without a trip to the rooftop terrace, where you can order a cocktail and admire the city views.

1. Ride the Water Taxi from the Loop to Chinatown for a dumpling-filled lunch. The $9 fee isn’t so bad, and the sights are unparalleled.

2. If it’s raining or snowing (as it often is in Chicago), follow locals underground to the Pedway, a system of underground tunnels that connect noteable downtown buildings.

3. Save a buck by checking out the National Museum of Mexican Art, the Block Museum of Art and the Chicago Design Museum—all of which are free to visit.

4. Yeah, yeah, we know you have to see the Bean. You’ll avoid the crowds (and get an amazing photo) when you visit early in the morning, around 7 or 8am.