The architecture in downtown Chicago is amazingly diverse. “These buildings have a natural relationship to each other,” says Wayne,
our docent, guide, jokester, and general Chi expert. “The styles talk to each other.”
We’re gawking and admiring from the Chicago River, as we glide through the city on The First Lady, a cruise boat for the Chicago Architecture Foundation. We started at DuSable Harbor (tip: park in the DuSable Harbor parking lot, under Lakeshore Drive at Randolph Street–$20 for all day, and you’re a short walk from Lake Michigan and the River Walk). We’ve had a fine lunch of grilled shrimp and tropical chicken salad at the Friendship Cafe, where Asian food is a specialty and outdoor tables offer good people- and boat-watching. (Another tip: Choose iced tea only if you like bottled diet Snapple). The cafe has live jazz on Sunday afternoons and Friday and Saturday evenings.
Aboard the First Lady, we sail by famous skyscrapers, from the classic Renaissance-style Wrigley Building to Trump Tower, the tallest all-concrete building in the world. Wayne describes the different styles: Art Deco, International Modern, Post-Modern, and others. Now I know what adaptive re-use is–a fancy term for recycling, as far as I can tell, fixing up an old building for modern use. I also know that Chicago has the most bridges (57) of any city in North America, a 90-mile tunnel system, and more boat slips than any other U.S. city. I learn that the Chicago River runs backward; instead of flowing into Lake Michigan (6th largest lake in the world) and polluting the region’s drinking water, it was dredged in the early 1900s so it would flow toward the Mississippi. “The river has been upgraded from toxic to highly polluted. Don’t eat the fish,” Wayne says with a wry grin, and adds, “They’re working on it, though.”
Curving walls echo the curves of the river as we glide down the north, south, and main branches of the river, passing people strolling and bicycling on the tree-lined walkway or sitting at outdoor cafes. Wayne is a fount of information on his beloved city. The Aqua at Lakeshore East is the tallest building in the U.S. designed by an architectural firm headed by a woman.
The Sears Tower, once the tallest in the world, is now the Willis Tower. Buildings stand on the air rights of railroads. Chicago has the most “green roofs” in the U.S., incentives to encourage environmentally sound development.
At the end of the 90-minute tour, we feel educated, entertained, and more than a little awed by the variety and imagination that went into Chicago’s architecture. It’s a marvel, and the best way to see it is on a river cruise. (May through November, $35.)

Just watched Ken Burns 3-hour program on Frank Lloyd Wright – seeing those beautiful buildings makes me wonder what he would have said – smile. Thanks./jj
Thanks, Jan. I’d guess FLW had plenty to say about Chicago and its designers! After that cruise, I have a whole new appreciation for architects.
This is totally awesome, Marilyn! Makes me want to jump on the train and ride the rails east to Chicago and visit the River Walk. Your docent Wayne obviously knows his stuff and the river cruise sounds like a fun way to see the interesting architecture and sights in the Windy City. Your lunch sounds totally delicious, even Allen C. would be impressed:)
Myrna, thank you! You’re right, the river cruise is a great way to see Chicago and learn somet of its colorful history. Did you know the first non-native settler was a man from Haiti, who established a trading post in 1772? The place has changed a bit since then.
I’m going to Chicago next week and although it will be colder, it’s always good to get an overview!
Thanks — Enjoy your time in Chicago, a great city.