Gotta Getaway: Chicago Is Better Than You Think (Even If You Think It’s Great)

On Ricky Gervais’ just-released-on-DVD HBO special Out of England, he mentions the fact that his entire U.S. tour consisted of only New York and Los Angeles, and that he skipped over “the middle bit.” As much as the people living on the coasts sometimes want to believe, there’s a copious number of people living in “the middle bit” with just as much thirst for the finer things as people in Manhattan or Southern California. And when they want to spend a weekend in a big city, many of them skip New York (too overwhelming) and Los Angeles (too big a logistical nightmare) in favor of Chicago. And now’s the time to go.

First, it’s easy (and cheap) to get to, as Chicago’s two airports both operate as gateway hubs for most of the major airlines. Even during heavy traffic seasons or over weekends, you can still get to Chi-Town for under $200 a ticket, and usually you can pay less.

Once you’re there, there are a handful of hotel deals to be had. We’re big fans of Kimpton properties, and right now they are having a special for the month of April where they will wave your room taxes, which is no small bit — sometimes upwards of $40 a night. For our money, the Hotel Allegro is the top of the heap. An eco-friendly property in the city’s theater district, it offers incredible in-room spa services and these spectacular giraffe robes. It’s also within walking distance of Catch 35, our favorite seafood restaurant in the Midwest.

There’s another fine reason to make the pilgrimage to the City of Broad Shoulders: the theater. If you go in the next few weeks, you can still catch Magnolia, a phenomenal new play written by Regina Taylor (star of CBS’ The Unit) that takes place in Atlanta in 1961 amidst desegregation and manages to capture the fear and exhilaration of a uncomfortably unified city.

Though we’ve never lived there, all our visits to Chicago have been great: it’s easy to get around, it’s got great restaurants, excellent theater, a lively local music scene, some quality spas and top-notch sports. So we ask you: is Chicago America’s most underrated city, or is there another cultural hub in the Midwest we’re missing out on?