The accidental tourist

Read on for a guide to some of Chicago’s best, most unique tours

By Amy Williams Bernstein

According to the Chicago Department of Planning and Development, this city is made up of 77 communities. But in practice, it’s divided into many more neighborhoods. Streeterville, Andersonville, Old Town, Wicker Park. These are all places I heard about when I moved to Chicago a year ago, but I couldn’t find them on an official map.

I found the guidance I needed on a tour. Chicago Neighborhood Tours, organized by the Chicago Office of Tourism, explore historic and ethnic neighborhoods. When I boarded a 40-person bus on a Saturday morning, I expected to join a group of out-of-towners curious to see what charms lie beyond Michigan Avenue, as I was. But the passengers I questioned were from Chicago neighborhoods like Bronzeville and the South Loop or from nearby suburbs like River Forest and Evanston.

That’s typical, I later learned. “Usually 70 percent of the people on my bus are Chicagoans looking to know their city better,” said guide Marshall Jacobson. This conversation sparked a realization: There is so much to see, do, taste and learn in this city that even locals can’t find it all on their own. To make the most of my new home, I would have to make like a local and take a tour… or 12.

Back in time
I started with a foray into a tumultuous time in Chicago’s history. The Chicago History Museum’s tour “Magic Bus: 1968 in Chicago” explored the year when Chicago hosted the Democratic National Convention. Guide Bill Siegel, an educator and filmmaker, incorporated writings, voice recordings and videos into his narration.

A touching moment occurred when the bus paused beside Grant Park, where thousands of anti-war protestors gathered that year. Siegel played news footage of bloody clashes between the protestors and police and solemnly read the result: 100 protestors injured, 100 policemen injured, more than 500 people arrested. Then Siegel invited us, a group that ranged in age from 20-something to 70-something, to share thoughts or memories. A white-haired man spoke up. He was a Chicago police officer assigned to crowd control in Grant Park at the time, he told us, and he spoke of what he witnessed with emotion in his voice. “It was mass chaos,” he said. “I saw some policemen going overboard and some cooling people out.”

In stark contrast to the reflective treatment the Magic Bus tour gave to 1968, Untouchable Tours turns the early 20th century heyday of Chicago’s gangsters into a rollicking affair. I invited two girlfriends to break up a dull work week with me on a weeknight Gangster Tour. At the end, my friends Marcy and Teshera agreed it was a little like attending a play on a bus.

Our guides used aliases — Johnny “Four Fingers” and Louie — and wore fedoras and loud ties. The two stayed in character, telling stories about Chicago’s mob bosses and hit men as if they were there, complete with wise-guy cracks. Of the shooting of “Big Jim” Colosimo, Johnny said, “after dat, he spent da rest of his life dead.”

The tour started in downtown with stories of the early immigrants who organized the city’s crime and traveled chronologically from there. Pausing in front of Holy Name Cathedral, we saw a bullet hole in the southwest corner of the church wall, evidence of the murder of bootlegger Dion O’Bannion, ordered by Al Capone. Later, we passed a construction site that was once the Lexington Hotel, where Capone made his headquarters and Geraldo Rivera came up empty-handed in his search for loot in Capone’s vault.

By design
The Chicago Architecture Foundation runs the most respected river cruise in the city. When my husband Stuart and I moved to Chicago, it seemed every new co-worker and friend asked if we had taken the river cruise. We heard this question enough that we had to take it.

Docent Gina Johnson narrated our voyage aboard a two-level boat. She explained that Chicago’s reputation for architecture began after the Great Chicago Fire of 1871 destroyed about one-third of the city. Some of the nation’s foremost architects were attracted to the opportunity to work with a blank slate. They developed innovative buildings, such as the 10-story Home Insurance building, completed in 1885 (and demolished in 1931) and considered the world’s first skyscraper. Notable architects have come here ever since.

Moving at a leisurely pace along the Chicago River, we saw some of modern-day Chicago’s most impressive buildings from a perspective not possible on land. But more than simply admiring buildings, Stuart and I enjoyed hearing the stories behind them. For example, the terra cotta-clad tower at 35 East Wacker Drive is nicknamed the “wedding cake” because of its tiered structure and elaborate detailing. Built in 1926, it was the Jeweler’s Building and had a 22-story indoor car elevator. This was a safety feature for the diamond merchants who worked in the building, so they didn’t risk being robbed while transporting jewels to their offices. The belvedere atop the building was a speakeasy during Prohibition. Now, it’s a showroom for contemporary architect Helmut Jahn.

Chicago Trolley and Double Decker Company’s hop-on, hop-off bus tour is many visitors’ introduction to the city. And like the river tour’s boat, the open-air top deck of a double-decker bus affords a unique perspective on the city. Just don’t stand up while passing under traffic lights.

The 13-stop main route hits major sites like the Sears Tower and Navy Pier. But I took the lesser-known ethnic route that heads off the beaten path into Chinatown, Little Italy, Greektown and the West Loop. These vibrant neighborhoods to the south and west of downtown look very different from the area that contains most of Chicago’s tourist attractions. There aren’t skyscrapers; there are lots of residential buildings, and there are businesses and restaurants where real Chicagoans work and eat and have been doing so for decades. It’s not easy to get to these neighborhoods without a thorough grasp of the public transit system, or a taxi, so the hop-on, hop-off service is a great way to explore. The on-board guides added context to my journey.

I hopped off in Little Italy, in front of a statue of Joe DiMaggio, who never played for a Chicago team. But, I learned, he was revered among the local Italian community for his fundraising efforts. The brick plaza surrounding the statue and the tree-lined street beyond seemed like the perfect place, I thought, to have a look around then catch the next bus.

The gift of experience
For Stuart’s birthday, I decided to give him what he always wanted, even if he didn’t know it: a Segway ride.

A Segway is a motorized scooter that a rider stands on. We signed up for a tour through City Segway Tours and met our group of seven at the northern end of Grant Park. At first, we eyed the self-balancing machines nervously as our guide, Kyle Gaffaney, showed us how to safely mount and dismount. When my turn came, I stepped onto the platform easily. I could feel the scooter moving slightly under my weight to keep itself balanced, but it didn’t take long to get used to it. Just as Kyle had demonstrated, I shifted my weight toward my toes, and the Segway moved forward. Then I shifted onto my heels, and it slowed and stopped.

We traveled on the sidewalks through Grant Park, and into Museum Campus, home to the Field Museum, Adler Planetarium and the John G. Shedd Aquarium. Earlier, City Segway Tours operations manager Wes Kimball had told me about half of his clients are primarily interested in a chance to ride a Segway. Guides take a personal approach to each group and adjust the amount of narration. Kyle peppered our journey with interesting facts, but, thankfully, he wasn’t offended when the group scattered like cats at the sight of some planters that looked like a great obstacle course.

I concluded Stuart’s birthday celebration with Shoreline Sightseeing’s romantic fireworks cruise on Lake Michigan. During summer, Navy Pier holds a fireworks show on Wednesday and Saturday nights, and these cruises depart about half an hour before the show starts to get in perfect position to watch.

After dark, Stuart and I boarded a two-level boat at Navy Pier and set off to the tune of “It had to be you.” There was no narration on this tour, but there was music to set the mood. First, we headed north, hugging the shoreline, which afforded a spectacular view of the Chicago skyline glittering as if it was the fireworks show. Then we made a U-turn and headed back toward Navy Pier. The show was a full 10 minutes of huge, Fourth of July-quality explosions. And the cool Lake Michigan breeze gave us an excuse to cuddle as we oohed and aahed as if we were seeing big-city fireworks for the first time.

The show must go on
Broadway in Chicago has brought some big-name numbers, such as “Wicked” and “Jersey Boys,” to its three historic venues in the downtown theater district. I already had a ticket to see “Avenue Q,” so when I learned of the company’s theater tour, I decided to check it out before my show.

The tour starts at the Ford Center for the Performing Arts, which is usually called by its original name, the Oriental Theatre. This 1926 movie palace is so ornate it’s impossible to see every detail in one visit. “There’s so much to look at in this theater,” said my guide, Amy Distel, as we entered the auditorium. And she pointed to a grotesque face that can only be seen from the spot we were standing. The décor borrows from a number of Asian cultures: Indian nobility depicted in mosaics, seated Buddhas in relief molding, and Japanese wood carving adapted for lamps. But it’s also rife with creatures born from the imaginations of the Rapp brothers, the architects responsible for some of Chicago’s most interesting theaters. In the auditorium, sea horses with elephant heads flank the stage, while winged gargoyles adorn the rim of the first balcony.

From the Oriental, the tour moves on foot to the 1906 Bank of America Theatre (often called the Shubert) or Cadillac Palace Theatre, depending on rehearsal schedules. I took in the 1926 Cadillac Palace and later returned to see Avenue Q. Laughing out loud at the show’s irreverent musical numbers was all the more meaningful because I knew I was doing so under a gilded Baroque ceiling.

The Oriental Theater also figured prominently in the ghost tour organized by Chicago Hauntings Tours. Stuart and I joined our friends Leah and Zeke on that tour, and we all heard for the first time that the Iroquois Theatre once stood on the same ground. Built in 1903, the Iroquois caught fire during a packed show only one month after it opened. More than 600 people died. The alley behind the Oriental is known as a spooky place where ghostly screams are sometimes heard. Some people, said our guide, David Cowan, feel an inexplicable dread when they enter the alley. On that note, our group of 12 brave (and living) souls followed David into the alley.

The bus tour’s most surprising stop was the site of the Eastland Disaster. In 1915, the S.S. Eastland, an excursion boat, capsized in the Chicago River, killing more than 800 passengers. The deadliest disaster in Chicago’s history happened beside what is now a busy section of Wacker Drive, the downtown thoroughfare that runs along the southern bank of the river. Even Zeke, a Chicago native, said he had passed this spot many times and never knew the significance. The Chicago police get lots of calls about bodies floating in the water here, David told us. But when they search, they find nothing.

Just plain fun
I inherited my love of chocolate from my mother. When she came in town, a chocolate tour was the natural choice for some mother/daughter bonding. Mom and I met our tour leaders, Karen Schaefer and Valerie Beck, on Michigan Avenue. Valerie, who owns Chicago Chocolate Tours, handed us each a brown paper bag and explained it was to save anything we didn’t want to eat immediately. I scoffed. Why wouldn’t I eat chocolate right on the spot!

Two chocolate shops into the tour, I was adding samples to my bag. My wiser mother started saving samples from the beginning, staving off chocolate overload. At each of seven stops — Teuscher, Lindt, Godiva, Frango, Vosges Haut Chocolat, Pie and Berry Chill — we received a free sample or two. And as we walked from one shop to another, Valerie often shared something she particularly wanted us to try, such as squares of a chile-spiked chocolate bar. That night, my mother left Chicago with a goody bag full of chocolates as her souvenir.

When my friend Christi, an avid cyclist, needed to entertain two friends visiting from Houston, I suggested she show them the city by bike. We signed up for a tour with Bobby’s Bike Hike.

The office is on a pretty little dock toward the eastern end of the Chicago River. We each received a bright green and white Schwinn cruiser with a comfortably wide seat. Our guide, Phil Brankin, a 21-year-old bike messenger, explained that on city streets our group of eight would ride as a pack, taking up a lane of traffic. We did just that when we pulled out of the dock and onto the street, and it was actually exhilarating to ride in the middle of the road, knowing there was safety in numbers. We headed south, past Millennium and Grant Parks, through Museum Campus and up a ramp into Soldier Field, where the Bears play. We made a full circle around the stadium, taking in the Greco-Roman columns remaining from the original 1924 stadium and the futuristic steel and glass structure added during the 2001 renovation. From there, we headed to the lakefront and rode back to our starting point amid throngs of joggers and Rollerbladers.

I can think of lots of things I’d rather do than shop — going on a lakefront bike ride for instance. And yet, when I heard about ShopWalk, a boutique shopping tour, I was intrigued. Owner Danielle Lutz leads public and private tours that hit Chicago-only stores in unique neighborhoods, such as Bucktown. Some stores give discounts to her participants.

I met up with Danielle and two ladies visiting from Phoenix at a Bucktown cafe. After she asked us a few questions to determine our styles and shopping needs, Danielle led us next door to Tangerine. We flipped through the racks, chose some pieces and headed to the dressing rooms. Danielle stayed close by to offer her opinion. I ventured out of my dressing room in a flame-red knee-length dress, and Danielle confirmed what I was thinking — it would be perfect to wear to a friend’s summer wedding. We hit seven stores in a four-hour shopping whirlwind. And I didn’t leave empty-handed. I admit it. I had a blast.

I’ve taken one tour for every month I’ve lived in the city. And my newfound knowledge makes walking around so much more exciting. I’m no longer surrounded by buildings and topographic features, I’m surrounded by stories. My landmarks aren’t visual, they’re historic facts and people. The other day, Stuart asked me where to catch a bus, and I told him it was just past the site of the Eastland Disaster, across the river from the Bertrand Goldberg towers. If you take a tour while you’re visiting the city, you can have that feeling too. Just don’t ask me for directions.

Chicago Neighborhood Tours
(312) 742-1190; chicagoneighborhoodtours.com
When: Most days of the week. No tours in December.
How much: $20-$50

Chicago History Museum
(312) 642-4600; chicagohistory.org
When: Most days of the week.
How much: $10-$75

Untouchable Tours
(773) 881-1195; gangstertour.com
When: Daily.
How much: $27

Chicago Architecture Foundation
(312) 922-3432; architecture.org
When: Most days of the week.
How much: $10-$85

Chicago Trolley and Double Decker Company
(773) 648-5000; chicagotrolley.com
When: Daily.
How much: $29

City Segway Tours
(877) 734-8687; citysegwaytours.com
When: Daily.
How much: $60-$70

Shoreline Sightseeing
(312) 222-9328; shorelinesightseeing.com
When: Daily, April-November.
How much: $14-$26

Broadway in Chicago
(312) 902-1400; broadwayinchicago.com
When: Saturday.
How much: $10

Chicago Hauntings Tours
(888) 446-7891; chicagohauntings.com
When: Tuesday-Sunday.
How much: $28

Chicago Chocolate Tours
(312) 863-8614; chicagochocolatetours.com
When: Friday-Sunday.
How much: $40

Bobby’s Bike Hike
(312) 915-0995
When: Daily, March-November.
How much: $27-$32

ShopWalk
(773) 255-7866; chicagoshopwalk.com
When: Call for tour schedule.
How much: $41-$70

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