Chicago: Have a Hot Time in Chi-town

The Second City serves up first-class sights, entertainment, shopping and, of course, hearty food.


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. 

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, 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.

Wendella, 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, Prices vary. 

Catch a Show

The reputation of Chicago’s theater scene has grown steadily since our world-class Steppenwolf Theatre produced the likes of John Malkovich, Joan Allen and Gary Sinise, and The Goodman Theatre transferred many shows to New York stages. CSI star William Petersen started here at the now-defunct Remains Theatre, and Friends star David Schwimmer co-founded the Lookingglass Theatre, which in 2003 moved into the historic Water Tower Water Works building on North Michigan Avenue, one of the few buildings to survive the great Chicago fire of 1871.

Steppenwolf Theatre Company,, tel. 312-335-1650
The Goodman Theatre,,
Lookingglass Theatre Company, tel. 312-337-0665
tel. 312-443-3800

Stop at the Hot Tix windows at 72 E. Randolph St. or 163 E. Pearson St. (the service accepts credit cards now) to find out whether dozens of productions—from the raucous Blue Man Group (my kids' favorite) to the innovative Chicago Shakespeare Theater (which has a great Short Shakespeare program that gives kids a fast-paced, action-filled introduction to the Bard) or the always bitingly funny (but rarely child-friendly) Second Cityis offering half-price tickets for performances that day. If not, take a chance on any of the lesser-known theaters. We have never been disappointed, whether it was a big national touring production of Wicked or a small experimental show at an Off-Off-Loop theater—but ask whether the production is family-friendly before buying a ticket for the kids.

To ensure kid-friendliness, opt for one of Chicago’s wonderful children’s theater groups. Our favorites are the wonderful Chicago Kids Co., which understands that little ones need to get involved in the show, and Emerald City Theatre Co. in Lincoln Park, which always has some terrific show on stage.

Chicago Kids Co.,, tel. 773-205-9600, Tickets: $10 Emerald City Theatre Co.,, tel. 773-935-6100. Tickets: $15-$37, adults; $12-$27, kids, depending on the show.


Chicago is home to a wealth of museums. There are the traditional favorites such as the venerable Art Institute of Chicago on Michigan Avenue, home to an impressive collection of Impressionists and a terrific Kraft Education Center that offers hands-on activities for kids. My daughter loved it until she turned 11 and realized she was far too sophisticated to spend her time down there when there were masters to see in the galleries upstairs.

There’s also the funky (and free) National Museum of Mexican Art, just west of the Loop in Pilsen. My kids have always been drawn to the vibrant colors inside the museum (you might want to preview the exhibits—some can be a little racy) but they are just as enamored of the art on the street in this pulsing ethnic community. Many neighborhood buildings sport rich mosaics or beautiful, sometimes religious paintings. Before you head back downtown, stop in at any of the storefront restaurants for a taco and a horchata, a Mexican rice-flavored drink.

Art Institute of Chicago, Admission: Free Thursdays from 5-8 p.m. Otherwise it’s $12 for adults; $7 for students and seniors, free for kids 12 and under. This used to be a “suggested donation.” Now it’s a mandatory fee.
National Museum of Mexican Art,, tel. 312-738-1503, free.

For the scientifically-minded, the Museum of Science and Industry near the University of Chicago campus in Hyde Park is not to be missed. My kids, museum regulars, love the coal mine (which can be a little dark, a little loud and little scary for young ones), the chick hatchery and the Fairy Castle. My husband never leaves without a long walk through the U-505 submarine, a special exhibit that requires an additional $5 fee.

Museum of Science and Industry, Admission: $11 adults, $9.50 seniors, $7 kids ages 3-11.

Most major Chicago museums offer free days. For a list, visit If you can’t make it to town for a free day, consider buying a CityPass ($49.50 for adults, $39 for kids ages 4-11). It’s good for nine days and includes admission to the Museum of Science and Industry, John Hancock Observatory (worth a trip only on a bright and sunny day when it feels like you can see forever), the Adler Planetarium, Shedd Aquarium and Field Museum.

Don’t miss

Lincoln Park Zoo, one of the last free zoos in the country, is set just west of the lake in Chicago’s huge Lincoln Park. Be sure to cover both extremes of this small and accessible zoo. Take the little ones to the south end to see the newborn animals at the Farm in the Zoo, then trek to the north end to say hello to the polar bears. The zoo has recently undergone major renovations, including the addition of the terrific Pritzker Family Children’s Zoo. Beware: It can be tough to drag the kids off the climbing structure and back outside, so don’t venture in until you’re ready for a rest.

Lincoln Park Zoo,, tel. 312-742-2000

Garfield Park Conservatory is one of the city’s best-kept secrets and one of my family’s favorites. Just 10 minutes west of the Loop, the conservatory is easily reached on the CTA Green Line, by cab or car (with the added benefit that it offers plenty of free parking, a rarity in any city these days) and it’s free. Grab a scavenger hunt map to help kids discover the secret lives of plants, or just take them straight to the Elizabeth Morse Genius Children’s Garden, where they can slide down a plant stem, climb a seven-foot seed or, my kids’ favorite, discover the Sensitive Plant, which is “so shy it cringes when touched.”

Garfield Park Conservatory,,
tel. 312-746-5100

And, finally, there are the tours of the city’s gangster history. We’ve done several with the kids. The best for serious ghost-hunters, believers in the spirit world and gangster scholars is Richard Crowe’s Chicago Supernatural Tours. Crowe calls himself an “internationally known Chicago ghost hunter,” and he certainly seems to know his stuff. But my son, then 13, got a little bored as the tour dragged on for four hours. Perhaps if we had actually seen a ghost that night (which Crowe says happens at times), we might have felt differently.

Chicago Supernatural Tours,, tel. 708-499-0300. Price: $39

Our preference, for pure kitschy fun, is the Untouchable Tour. Unlike Crowe, who rides around in an air-conditioned coach complete with bathroom, this gangster tour is a little like Chicago itself: gritty and tough. Using a converted school bus decked out with fake bullet holes, our tour guide, Southside, knew how to make Chicago’s bloody history fun, and make fun of Chicago’s bloody history. Just remember, when Southside yells “duck,” you’d better do it. My kids laughed for most of the two-hour tour, and I was impressed to realize they actually ended up learning something about Chicago history when, several months later, they were regaling family members with stories of Chicago history, courtesy of Southside.

Untouchable Tour,, tel. 773-881-1195. Prices: $25 adults, $20 kids.

Destinations: Chicago

Themes: Family Travel, Urban Endeavors

Activities: Arts and Entertainment, Museums, Sightseeing

User Comments

This totally makes me want to visit Chi-town! Great article.

Huh. Chicago is cool! I've got to check out this city. It sounds like a blast!

Great "shopping" list I'm printing this article out and taking it along with me on my next trip to Chicago!

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