Chicago Travel Guide

The first baseball game Chris Kennedy ever saw was in Fenway Park, in Boston. “We were late,” he remembers. “Of course, with 11 brothers and sisters, we were late for just about everything.”

Today, Kennedy is in a car being driven from his office at Chicago’s Merchandise Mart (he’s been the president of Merchandise Mart Properties since 2000) to yet another meeting in yet another place. And he’s having yet another telephone conversation. But unlike most of the others, this one unmistakably puts a smile in his voice as he continues his story.

“And I’m walking down Lansdowne Street, and a home run comes over the Green Monster [Fenway’s 37-foot-high left-field wall] and lands five feet in front of me. Nearly took my head off. And I thought, ‘Wow, this is exciting! This is a thrill.’”

For 25 years, Chris Kennedy—son of Bobby and Ethel, nephew of Jack, Teddy, Eunice and Sarge, child of Massachusetts and suburban Washington, D.C.—has been a Chicagoan. A job out of Boston College and the girl he would marry lured him here in 1986; marriage, children, work and earning an MBA (at Northwestern’s Kellogg School of Management, class of ’94) would keep him here. Plus, the man seems to like the place.

Born on the Fourth of July, 1963, Kennedy now runs a company that manages properties in Los Angeles and Boston, as well as Chicago’s 4.2-million-square-foot trade center, opened in 1930 by retailer Marshall Field & Co., later owned by Kennedy’s grandfather Joe, currently a division of Vornado Realty Trust and still the largest commercial building in the world. The number of boards and nonprofits to which Chris Kennedy belongs and/or contributes time is astonishing for a man with a full-time job. The number of times he has been asked about running for political office is—well, let’s stay on message.

The Message is Chicago

“There’s no faith as strong as the faith of a convert,” Kennedy says. “I’m a transplant here. The city has a long history of welcoming immigrants, not only from other countries but from other cities and states. Maybe that’s why I feel so comfortable here. I’m a believer in Chicago.”

It’s a city that’s not like other cities, he says, and you see it especially in Chicago’s neighborhoods. “[In] Washington, they really didn’t have a great ethnic sense. In fact, at the time I was growing up and in that city, there was a certain amount of political correctness where ethnicity was not emphasized.” Chicagoans, on the other hand, “embrace their ethnicity,” he says. “Not to say they’re better, but just to say they’re different, and they’re proud of where they come from.”

And that, he says, is the Chicago visitors should discover. The obvious sights—the museums, the ballparks, the skyscrapers—are fine. But “if I were a visitor to Chicago, I’d figure out whether I’m Irish or French or Italian or African American, and I’d go to one of those restaurants,” says Kennedy. “Go to a place that celebrates your heritage: Swedish restaurants in Andersonville. German restaurants. If you’re Italian, I’d probably go out to Tufano’s Vernon Park Tap [in Little Italy]. Get out from just going to a great steak joint one night.”

Have to Ask: Fenway or Wrigley?

“You know, you can only fall in love once, I guess,” Kennedy says. “But in Chicago, I like U.S. Cellular Field. I love going to a game at the White Sox park. It’s a fun park to go to with the kids. Not the answer you thought you were going to get.”

Eating Around

“[This] is such a good restaurant town that you expect to have a great steak and a fresh cut of fish,” he says. “And we’re in the Midwest, so the quality of vegetables is always excellent. The restaurants differentiate themselves by the people who run them. Getting to know some of the restaurateurs here—at Keefer’s [steaks, seafood], or the folks who run Coco Pazzo [Italian]. You go to Kiki’s Bistro [French] and hear Kiki’s story about coming over from France. There are amazing stories for every one of the restaurants here.”

Plus, he adds, “I also think there’s sort of a political theme, if you want to go that way.” Politics has long been considered Chicago’s real favorite sport. “Go to the Billy Goat [burgers], underneath Michigan Avenue, and get a sense of what it was like with [late legendary columnist Mike] Royko down there and reporters meeting with a bunch of politicians. Or go to Gene & Georgetti’s [steaks], where [the late onetime congressional powerhouse Dan] Rostenkowski used to hold court.”

Aside from its steakhouses, Chicago is best known, culinarily speaking, for its hot dogs, pizza and Italian beef: the latter being thin-sliced roast beef in a garlicky jus, served on crusty bread and ideally soaked in that gravy, and the whole sandwich garnished with sweet peppers. Italian beef is not date food.

“The best hot dog is probably Irving’s for Red Hot Lovers, which is in Wilmette.” (The Kennedys live in Kenilworth, a northern suburb near Wilmette; Chicagoans argue about hot dogs and pizza the way Philadelphians argue cheesesteaks.) “The best pizza is Lou Malnati’s. I have a gluten allergy, and they have a gluten-free pizza at Lou Malnati’s—it’s an all-sausage crust. It’s unbelievable. It’s good for your stomach and bad for your heart. And, of course, Al’s Italian Beef, up by the Merchandise Mart. The best french fries in Chicago are at the new French Market,” located at the downtown Metra commuter-train station. “They’ve got a place that just sells french fries”—Frietkoten Belgian Fries and Beer—“and it is just phenomenal.”

Nightlife

“Chicago’s the third-largest city in the United States, so every act comes through here. Nobody can avoid Chicago,” says Kennedy. “I’d grab a copy of the Reader or go to the WXRT website and see who’s playing at the Double Door or the Riviera or the Metro. See what the live music is like.”

“The theater scene is unbelievable, particularly with all the big commercial operations that are now a part of the Loop—but those are a lot of the national touring companies you can maybe find in other cities as well. Finding what’s unique about Chicago is the most important thing: Find out what’s happening at Steppenwolf or at the Goodman. You can’t go wrong with either of those.”