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Kayaking on the Chicago River and three more tours of the Windy City

Kayaking on the Chicago River and three more tours of the Windy City

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I’ve been to Chicago several times, and on each visit I tend to hit the same places — the Art Institute, Shedd Aquarium, Millennium Park. »» This time I wanted to see new sights in the city, so I went to the experts: Chicago tour guides. »» When I started my search, I found tours of all kinds: bike tours, Segway tours, haunted tours, comedy tours. I settled on some criteria to narrow down my list: Each tour had to be active, each had to have a historical emphasis and each had to go beyond the obvious bus, boat and museum tours. »» Here are the four ways I explored the Windy City.


Tour operator • Chicago Detours,, 1-312-350-1131Difficulty • EasyCost • $26, $18 for kids, free for children under 5

Distance • ½ mile

Duration • Two hours

What to wear/bring • Comfortable shoes and an umbrella if it’s rainy.

For whom • Anyone with an interest in architecture and/or Chicago history.

Other tours offered • Historic Chicago Pub Crawl Walking Tour ($34), Best Architecture Walking Tour Since Sliced Bread ($22).

What makes it different • Tour is interactive with videos and photos shown on an iPad.

The first tour of the trip was led by the group Chicago Detours. My husband and I met our friendly guide Elizabeth Tieri in the lobby of the Chase Tower, the curved modern skyscraper on Dearborn Street next to Marc Chagall’s outdoor wall mosaic “Four Seasons.”

Tieri gave us maps of the eight stops on our walking tour. She then showed us her iPad, loaded with images and videos that would help explain the history of the city. Because Tieri is doing the storytelling throughout the tour, one of the tour group members (that would be me, in this case) carries the iPad and displays the visuals.

While the iPad wasn’t really necessary — Tieri knew her stuff and was an enthusiastic storyteller — it did add some novelty to the tour. We watched old videos of Studs Terkel talking about the “L” train and saw archive photos of buildings from the 1893 World’s Fair.

One difference between this tour and other architectural tours is that we didn’t just look at the outside of the buildings, we went inside many of them. Most surprising was the Chicago Temple Building, a skyscraper that’s home to First United Methodist Church, the oldest church in the city. It looks more like an office building until you walk in and see the neo-Gothic sanctuary. Stained glass windows (which do not actually face the street; they are lighted from behind) depict both religious images and Chicago landmarks.

On the second half of the tour, we visited the area that I was most curious to see, the Pedway. The maze of underground tunnels throughout downtown covers about five miles. It is a welcome way to get around during the brutal Chicago winters, but it is a sprawling system with a complicated, disjointed layout. We went from the Marshall Field’s building (now Macy’s) to the beautiful Chicago Cultural Center, but not many people were using the tunnels because sections of it are closed on the weekends (our tour was on a Saturday).

We parted ways with Tieri at the Cultural Center but not before stopping by the center’s magnificent Tiffany dome. The artwork, 38 feet in diameter with about 30,000 pieces of glass, is worth seeing whether you’re on a tour or not.


Tour operator • Kayak Chicago,, 1-312-852-9258Difficulty • ModerateCost • $65 per person

Distance • About 5 ½ miles

Duration • Three hours

What to wear • Plenty of sunscreen, a hat, sunglasses and shoes that you don’t mind getting wet. We also brought along a snack and water — you’ll want both.

For whom • Tourists with a sense of adventure who don’t mind getting wet or working the upper body.

Other tours offered • Lake Paddle ($65), Fireworks Paddle ($65), City Lights Paddle ($55) and Sunset Paddle ($55).

What makes it different • You’re in a kayak.

For a different vantage point of the city, take a kayak out on the Chicago River. We drove to the meeting point of Kayak Chicago, next to Goose Island, northwest of downtown. There we each got a life jacket, selected our kayak (single and doubles are available) and received a quick tutorial on kayaking from our guide, Brian Westrick. We put our keys and cellphones in Ziploc bags and then got in our boats.


As we started paddling we heard about William Ogden, creator of Goose Island and first mayor of Chicago. When our guides wanted to talk to our group of 23, we clustered our kayaks together and held on to one another’s boats. If the boats spread out too much, it could be difficult to hear the guides.

We proceeded to navigate near the massive Merchandise Mart, built by Marshall Field and Co. At one time the largest building in the world, it was a place for wholesale goods to be sold.

Farther down the river, we looked at the shiny Trump International Hotel and Tower, 98 floors tall with giant letters displaying its owner’s name, and the Art Deco Carbide & Carbon building with the distinct champagne bottle-shaped top.

As we encountered bigger boats, we veered to the right side of the river to stay out of the way. One thing to note about the river: It’s dirty. (When I spoke to Kayak Chicago founder Dave Olson after our tour, he noted that it had rained before our trip, and that more trash goes into the river during the rain.) Our guides reassured us that the river is much cleaner than it once was. Kayak Chicago even hosts events to help clean up the water. Nevertheless, when you’re paddling on the far right side of the river you’ll see empty plastic bottles and other garbage. At one point a dead rat floated by us. I tried to avoid splashing water on myself after this sighting.

But overall, even as inexperienced kayakers, we felt safe on our trip. The three guides with our group were confident, not just in their knowledge of the area, but in directing us during busy times on the water. They carried radios that they used to talk to one another and boat captains on the river.

Just remember to wear plenty of sunscreen. We missed some spots and are still paying the price with some patchy sunburns.


Tour operator • City Running Tours Chicago,; 1-877-415-0058. City Running Tours has locations in 17 U.S. cities.Difficulty • ModerateCost • $30

Distance • 5K (3.1 miles)

Duration • One hour

What to wear • Running shoes, workout clothes.

For whom • Casual runners with an interest in history.

Other tours offered • Haymarket Riot and Brewery ($40), Chicago’s Front Yard ($30), Uptown Andersonville Beer Run ($40).

What makes it different • You learn about the city during your morning workout.

The iconic “Bean” sculpture at Millennium Park is pretty deserted at 7 a.m. Monday, so it was easy to spot our City Running Tours guide Blake Williams. After some quick introductions and discussion about our experience level, we started our run. Williams adroitly dodged the morning rush hour foot traffic, pointing out the historic Monadnock Building by architects Burnham and Root. The steel-frame structure was the largest office building when it was completed in 1893 and is still home to hundreds of business firms.

As we continued, we hit some of the spots that gave the tour its name, places where tragic, newsworthy events happened. According to Williams, the years 1903 to 1919 in Chicago were a particularly disastrous time.

At the site of the Oriental Theatre on Randolph Street was once the Iroquois Theater, where a fire broke out in 1903 that killed more than 600 people, many of whom were trampled or jumped from the building to their death. When Williams saw our horrified expressions, he just looked at us sympathetically. “You’re welcome,” he said. After all, we knew what we signed up for.

And then there was the Eastland on the Chicago River. On July 24, 1915, Western Electric Co. hired the excursion boat for its annual company picnic. When more than 2,000 people got on the boat, it started to tip and eventually capsized in the river. The 100th anniversary of the disaster, in which more than 800 people died, will be commemorated July 24 at the Riverwalk along the Chicago River.

Grim stuff. Next time we go out with City Running, we’ll opt for the brew run.


Tour operator • Chicago Planet Food Tours, 1-312-818-2170, chicagofoodplanet.comDifficulty • EasyCost • $55 per person, $35 for ages 12 and younger

Distance • 1.3 miles

Duration • Three and a half hours

What to wear/bring • Comfortable shoes and pants with a forgiving waist. Also an umbrella in case of rain.

For whom • Foodies who want to try authentic Chinese cuisine.

Other tours offered • Gold Coast and Old Town ($45-$48), Bucktown and Wicker Park ($45-$48), Lincoln Park ($35).

What makes it different • This tour uses food to help illustrate the town’s Chinese history.

We had our morning run with City Running, and now we were ready to eat. Chicago Food Tours did not disappoint. We rendezvoused with tour guide and Chicago native Carlyn So in the lobby of the Triple Crown restaurant, near the Chinatown gate that greets visitors to the neighborhood.

After we sat down at our table, we looked through the helpful booklet So gave us that listed the places we would visit that day and provided a map of China that explained the characteristics of Mandarin-, Szechuan-, Canton- and Shanghai-style cuisine. So also gave us a few etiquette tips, starting with the tea pot on our table. It’s impolite to pour tea for yourself, So said. Instead you should serve others and then wait for someone else at the table to pour your cup. Empty teapot? Turn the lid upside down or lean it on the top to signal to servers that you need more. And to say thank you at dim sum? Tap your index and middle finger on the table together.

Triple Crown’s dim sum is typical of the food of Canton. The small plates, like Chinese tapas, that we tried included a taro puff, a deep fried nest of the root vegetable stuffed with pork; chia shu, a steamed barbecue pork bun; siu mai, a pork and shrimp dumpling; and a rice crepe filled with vegetables. This was just the first stop — we knew we had to pace ourselves.

Just a few of the other dishes we tried were lotus mooncake — kind of like a super-dense Fig Newton— at Chinese bakery Chiu Quon, spicy Ma Po tofu at Szechuan restaurant Lao Sze Chuan and Peking duck at Mandarin spot Lao Beijing.

At each of the five eating establishments we visited, we only stayed about 15 to 30 minutes. The rest of the time we walked around the neighborhood. We stopped and burned incense at a Buddhist temple and visited the Ping Tom Memorial Park along the Chicago River, in the newer part of Chinatown.

At our last stop, Saint Anna pastry shop, I swore I wouldn’t eat — I was just too full. But then So brought out a creamy egg custard tart. I ate the whole thing. I should have tapped the table to show my appreciation.

Jody Mitori • 314-340-8240

@jmitori on Twitter



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Chicago is known for it's architecture and tours that explore the city. Some are more off the beaten path, like a kayak tour along the Chicago…

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