Chicago: Have a Hot Time in Chi-town

We Chicagoans are used to the reactions of outsiders when we tell folks where we’re from. Snooty coastal residents might scoff and call Chicago a “fly-over city.” Less sophisticated acquaintances are likely to turn their hands into makeshift machine guns and spray the air with a “rat-a-tat-tat” (an all-too-common reaction that was blissfully interrupted during the 1990s when they instead asked, “Do you know Michael Jordan?”) 

To us, though, Chicago is the beating heart of the Midwest, the shining jewel of the lakefront. We know this City of Big Shoulders is really a city of small neighborhoods, that our theater scene can hold its own against Broadway, that on the beauty scale, we rank a 9.5, thanks to our long-running, tree-hugging leader, Mayor Richard M. Daley (who is still is referred to as “Richie” while his late father, Richard J. Daley, is affectionately known as “da real Mare Daley”). 

And we know that lots of what’s best about our town can be traced back to a certain cow. If Mrs. O’Leary’s heifer hadn’t knocked over that lantern, burning to the ground much of the shabby old Chicago, chances are we wouldn’t have such a vibrant city today.  

It is easy to navigate, thanks to streets laid out on a grid system (ask city residents where they live and they are likely to offer coordinates—2600 North and 400 West, for example—rather than an actual address). The city also might not have become a haven for architectural fans or lake lovers if it weren’t for the visionaries who flocked here in the wake of the devastating 1871 fire. 

• Good weather in Chicago brings bicyclists and swimmers to the lakefront.
• Ryan Dickey

So fly into rather than over Chicago, and discover the delights we natives know. And, yes, it includes a gangster tour that’s worth the money. 

See the Landmarks

This is best done from the Chicago River, provided the weather is cooperating. The Chicago Architecture Foundation runs bus tours, walking tours and river tours. Opt for the river tour, especially if you have kids in tow. My kids were bored silly by the droning commentary (which my husband and I listened to with rapt attention). But they were wowed by the underside of the city’s moveable bridges (Chicago has more than any other city in the world) while we stretched our necks to look up at the towering modern skyscrapers and turn-of-the-century marvels of early engineering know-how.

Chicago Architecture Foundation, www.architecture.org. Boat tours: $28 weekends and holidays, $26 weekdays through Nov. 18. Walking tours: $15 year round.

For a lower cost option, hop on board the Wendella for a ride up and down the river and through the locks (a crowd pleaser in itself) and alongside Navy Pier for a quick jaunt out to Lake Michigan. Or just take the water taxi. My kids snap up any opportunity to be on the water. Buy an all-day pass for $4 and hop on and off as you please.

• Home of the Cubs viewed from Wrigley's second deck.
• Jeramey Jannene

Wendella, www.wendellaboats.com. Combined Lake and River Tour: $22 adults, $20 seniors, $11 kids 11 and under.

No trip to Chicago during baseball season is complete without catching a Cubs game at Wrigley Field. To act like a real local, take the CTA’s Red Line "L" to the Addison stop, which is a block away from the park, and opt for a day game (some fans still have not forgiven the owners for adding lights and allowing night games). Once New York’s Yankee Stadium is torn down and replaced in 2009, Wrigley Field, built in 1914, will be one of only two remaining classic ballparks, the other is Fenway Park in Boston. Sit among the Bleacher Bums—some of the most devoted fans in baseball—and feast upon Chicago’s signature dishes: the Vienna Beef hot dog and Polish sausage.

Wrigley Field, chicago.cubs.mlb.com. Prices vary.