With summer in full swing, it’s a great time to show off the city to friends and relatives, as well as take a fresh look at it yourself. We recently toured the city by air, boat and bus–and with each tour, we saw the city, both literally and figuratively, from a different perspective. Here’s how we saw the city from our three distinct vantage points:
BY AIR, Chicago’s soaring skyline was a postcard come to life, a melange of cloud-scraping, steel-and-glass towers made even more dramatic against the expansive backdrop of Lake Michigan. But at one moment, as we peered out of the Beechcraft Sundown’s rear window and gazed directly below, all we saw was blue-green. Lake Shore Drive’s condominium buildings still could be spotted over our shoulders, but below us it was water, water everywhere.
Pilot Sebastian Fedko, a flight instructor with The Flight Center at Service Aviation in Wheeling, had shifted from his southbound flight path and was steering our four-seater plane east over Lake Michigan.
“There’s building interference,” the flight instructor said, and his radio communications with Meigs Field were breaking up. “So, I’m heading into open waters and will try again.”
Permission from Meigs to circle the Loop was granted, and soon we were sweeping by Chicago’s skyscrapers, seemingly only a softball’s slow-pitch away from the upper floors of the Sears Tower. As we circled the Loop, I drank in the view.
Although controllers had granted permission, they added that downtown fly-arounds were being discouraged. A ban by the Federal Aviation Administration restricting pilots of small planes expired in April, despite protests by city officials. The no-fly zone was put into effect after the Sept. 11 terrorist attacks. However, pilots must observe rules that restrict how close they can fly to high-rises.
Earlier that morning from Palwaukee Airport, our takeoff had gone smoothly. After taxiing down a small maze of runways and awaiting clearance, Fedko had fired the engines. With the words “We’re good to go,” we soon were airborne. Fedko steered the plane over Glenview and Wilmette, following Lake Michigan’s shoreline into Evanston and the city. Our 60-minute fly-around was private and peaceful, the skyline stunning and splendid. But our sightseeing tour was exactly that: seeing sights. Our pilot, busy keeping an eye on the sky, didn’t provide much in explanations about landmarks.
BY BOAT, it became evident that Chicago is a city at work, built for business and by innovators striving for superlatives such as tallest and first-ever. It’s also, we were reminded, a city with unpredictable weather.
As we boarded Chicago’s Little Lady for the Chicago Architectural Foundation’s river cruise, immediately a deckhand gaveus sheets of paper towel. A cloudburst minutes before had soaked the green plastic deck chairs, and passengers already were busy mopping. However for the 90 minutes of the tour, the gray clouds held their moisture, and it was clear sailing on the Chicago River.
Tom Reynolds, a CAF docent and retired Chicago police sergeant, greeted passengers and wasted no time launching into what would be a mini-course in Chicago’s dominant architectural schools and their stars. The tour headed up the river’s North Branch as far as Goose Island, the South Branch as far as Marina City and to the lake at Navy Pier and included more than 55 buildings along the way.
BY BUS, Chicago appeared to be a city of adventurers, attracting colorful characters and, at the moment, tourists pursuing fun and culture.
From the open-air top of a double decker bus, guide Sonia McWilliams busily pointed out South Michigan Avenue landmarks: Orchestra Hall; the Fine Arts Building, formerly the Studebaker Co., where carriages were made; Auditorium Theater; Chicago Hilton and Towers, once the world’s largest hotel; and Columbia College–her alma mater.
“This is where you spend $50,000 to learn to be a tour guide,” quipped the Chicago Double Decker Co. guide.
The tour covered 13 miles and two hours. It went as far south as Soldier Field and the Museum Campus, as far north as the Water Tower, as far east as Navy Pier and as far west as the Sears Tower and River North. An all-day pass allowed people to hop on and off at different stops along the route. Its atmosphere was lighthearted and packed with city lore, including tidbits on the Columbian Exhibition of 1893, the Chicago Fire, Al Capone and Oprah.
The breakdown
The best photo-ops: For the snap-happy, the air tour has the most stunning vistas. But be warned: The wing tends to get in the way. The boat tour offers opportunities for dramatic, neck-craning shots of skyscrapers and may be easier to capture. By bus, you’ll get shots of landmarks, such as Buckingham Fountain and Soldier Field, not seen on the other tours.
The most romantic: Pilots recommend taking the air tour at night, and many say they’ve had couples get engaged during flights. But if you’re into long-distance relationships, the river and bus tours can be great places to meet out-of-towners.
Highest fun and trivia quotient: The Chicago Co. Double Decker tours managed to keep us entertained for a full two hours with trivia that ranged from the city’s most expensive hotel rooms to a list of innovations from the Columbian Exhibition of 1893 (Cracker Jacks, movable sidewalks, the Ferris wheel, the Pledge of Allegiance, the kinescope . . . who knew?).
The best I.Q. booster: You’ll feel like you’ve had a crash course in Chicago architecture after your first Chicago Architectural Foundation cruise.
A wing and a prayer
Along with each tour’s thrills are some chills:
Resist the urge to look up while passing under Chicago River bridges during a boat cruise. Chicago Architectural Foundation docent Tom Reynolds said passengers who stare up at the bridges, mouths agape, risk being greeted by falling soot from the traffic and by pigeon droppings.
Hang onto your stomach if you’re flying. We experienced a stomach flip or two during takeoff and landing. Pilot Sebastian Fedko, calmly pointing out the barf bag in the seat’s rear pocket, said, “We have students get sick all the time.”
Get ready to duck if you’re on the double-decker trolley. On several occasions during the tour, low-hanging branches would have slapped us in the face if we hadn’t sunk into our seats for cover.




