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Cop Gives Offbeat Chicago tours

September 22, 2011 By: Travel Agent Central Contributor

Christine McConville, Boston Herald, September 22, 2011

"I'm a South Side Irish-Catholic Democrat, and White Sox fan.

"Oh, and cop."

It's a glorious day in downtown Chicago, and Dennis McKenna is taking a few minutes to describe himself to two people he's just met.

But those who already know describe him as Chicago's best tour guide.

McKenna, 71, runs See Chicago With a Cop (, a tiny company whose motto is "You won't get bored, and we'll have fun."

This spring, I spent a week in Chicago, a city where I spent most of my 20s, to see old friends, familiar sights and new landmarks.

A friend in the city's cultural-affairs office booked me a day with McKenna, who arrived at my downtown hotel promptly at 9 a.m. with Chicago Transit Authority day passes.

"Public transportation is the best way to see a city," he explains.

McKenna launched his business while working as a beat cop on the Magnificent Mile, an ultra-chic stretch of boutiques on Michigan Avenue.

"Chicago is a city of neighborhoods, great neighborhoods," said McKenna, who spent 34 years patrolling the city's streets. McKenna shapes each tour around clients' interests, but likes the impromptu rambles best. "The best plan is to just go out and see what we see," he said.

"A lot of times, we'll be heading out to see one thing, and then get sidetracked by something else that is going on."

On my tour, we gawked at a millionaire's mansion, saw a cathedral's newest addition and navigated some long-forgotten tunnels under City Hall.

We heard about McKenna's family, marveled at the ornate ceiling at the former Marshall Field's department store and met a former Secret Service agent, out for a lunchtime stroll.

"You live here your whole life, you know people," he says with a shrug.

It seems that the only thing he won't do is take people to dangerous neighborhoods.

"If someone wants to go, I'll give them my number, and tell them to call me from the hospital," he said.

It's close to 2 p.m. now, and our outing is coming to an end.

I've arranged to meet a friend at City Hall, so we go there.

It happens to be one of longtime Mayor Richard M. Daley's last days in office, and he's holding an open house of sorts.

But by the time we arrive in the mayor's ornate offices, Daley looks ready to stop shaking hands. Then, he spots McKenna.

"Officer," he says, after his aides usher us closer.

"Mr. Mayor," McKenna replies. "I'd like you to meet my friends from Boston."

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By Travel Agent Central Contributor | September 22, 2011
Christine McConville explores Chicago with an unusual tour guide.
Filed under : Midwest