Chicago Chic

Chicago Chic lobby with dog When Frank Sinatra crooned in 1964 that Chicago was his kind of town, the Sears Tower ruled the sky, Frank Lloyd Wright had invented 20th century architecture with Prairie-style designs, the Art Institute was amassing the largest collection of Impressionist art outside The Louvre, and deep dish pizza destroyed diets.

Half a century later, Chicago has retained all of that Americana culture while moving forward with a more globally-attuned food, art and design sensibility to keep it current with its big city brethren from New York to Shanghai. But to really experience this metropolis to the fullest, you need to put on your comfortable shoes.

“Chicago is one of those cities you just have to get out and explore. You can do a reception in a ballroom anywhere, but when corporate groups consider Chicago, they think art and architecture tours and food,” says Lauren C. Banks, national sales manager for PRA Destination Management Chicago.

Riverboat tours of Chicago’s famed skyline top the list, say planners and DMCs. Historic architectural wonders along the Magnificent Mile preen with ornate Art Deco era designs rooted in modern steel-framed skyscrapers and walls of glass, embellished with Greek and Roman influences.

“It’s like being in a canyon going through the Chicago River because you’re surrounded by architectural structures,” describes Kate Nelson, account manager for the DMC, Chicago Is. “The strongest reactions are to the Marina City towers, locally referred to as the ‘corncobs,’ and the Wrigley and Jewelers buildings.”

Some cruise lines deliver the straight skinny on historical facts. Others rely on quirky anecdotes by architecture students to pump up the drama: “See that large dome atop the Jewelers Building? Al Capone ran a speakeasy there during Prohibition.”

Public cruises run 60-90 minutes, which works well for conference groups under 100 willing to share space, says Ashley Sawyer, project manager for First Incentive Travel of Orlando. “However, I had 200 architects on a 2-hour private riverboat tour and they just couldn’t get enough.”

Nelson cautions that rule #1 for planners is, “Check the top deck’s capacity. Make sure your group is there. If they can’t enjoy the skyline, it’s not the same experience. Also, don’t serve a box lunch on a tour under 90 minutes. Why detract from the skyline? If you want to cater a meal, lengthen the cruise and have it below.”

For her VIP groups, Nelson rents smaller private vessels, extends the trip out to Lake Michigan and finishes at Fulton’s On The River. “It’s unique among area restaurants because they have a dock. It’s pretty impressive parking your boat alongside their terrace that holds 300. On a clear night it’s pretty fabulous.” So is their steak, seafood and service, she says, but she gives a really big thumbs up for her fave, the lobster mac ’n cheese.

Sawyer likes combining a boat cruise with photo ops from the Skydeck glass box jutting out atop the Willis Tower. “They don’t allow private tours, but a group under 50 can stay together if you go early.” Add a catered lunch for up to 200 in the Tower’s private room a floor away or lunch at The Signature Room on the 95th of the John Hancock Center so “your guests get excellent food and amazing views of Chicago’s skyline.”