Roughly two-and-a-half hours by plane, with direct flights departing from Jacksonville International Airport.
Where to Stay
Visitors to The Langham, situated in the middle of downtown Chicago, can get a feel for the city action by day and relax at night with views of Lake Michigan. A 3,000-square-foot lounge on the hotel’s uppermost floor—open to members only—features panoramic views as well as a breakfast buffet, all-day refreshments, afternoon tea and premium bar service. Thanks to numerous amenities—a spa and health club, indoor pool—the Waldorf Astoria is another luxe option.
What to Do
The 360 Chicago Observation Deck invites guests to view The Windy City from 1,000 feet in the air. To get a closer look at the stunning architecture and downtown views, take a leisurely stroll down the Chicago Riverwalk. On one side, walkways hug the Chicago River and on the other side is a seemingly never-ending string of bars, shops and restaurants. The Green Mill cocktail lounge is legendary in these parts. Back in the 1920’s, Al Capone and other gangsters used to socialize here, but these days it’s a go-to to take in local jazz music and grab cocktails.
Where to Eat
Exposed brick and leather banquettes make Au Cheval a romantic lunch destination, though it’s the classic burger (which many critics have dubbed the best in town) that draws the most guests. The wait is almost always long but the hand-formed patties, layered with American cheese and dressed with Dijonnaise and house made pickles—are welcome rewards. Of course, Chicago is renowned for its pizza and Pequod’s Pizzeria knows how to bake a deep-dish pie. The casual, brick-walled pub serves its caramelized crusts until 2 AM, so it makes for a good late-night bite. Settle in to a booth at the darkly romantic Bavette’s—another establishment by Au Cheval restaurateur Brendan Sodikoff—in the River North neighborhood for a crispy wedge salad, steak frites and a perfectly prepared Dark & Stormy. ♦