There’s an icy breeze, whipping in off Lake Michigan, making short work of the woefully thin jacket I’ve brought along to the Windy City. Chicago is certainly living up to its nickname on this cloudy spring day, but it’s a small price to pay for the opportunity to soak up one of the most impressive city skylines on the planet.
“Chicago has always been a laboratory for architects,” explains our guide over the loudspeakers, as our river cruise makes a turn at Navy Pier and heads back into the network of canals that flow through downtown Chicago.
We sail past buildings designed by some of the greatest names in architecture. Frank Lloyd Wright first made a name for himself in the city, and the skyline bears the signature of everyone from Louis Henry Sullivan to Jeanne Gang.
Although open-top bus tours are a fine way to explore the city streets, to appreciate the skyline of America’s third-largest city, it’s hard to beat the Chicago Architecture Foundation River Cruises aboard First Lady Cruises.
As we sail under the DuSable Bridge, named for the Frenchman who settled the city in the late 1700s, Trump International Hotel & Tower rises above us. The US president’s surname is emblazoned across acres of glass, which draws conflicting murmurs from groups across the boat. The structure is big and brash, not unlike its namesake, and far from the most attractive building Chicago has to offer. Look north rather, to the neo-Gothic Tribune Tower and the graceful Wrigley Building. South of the river, the Chicago Board of Trade Building is one of many inspired by the Art Deco movement.
While these architecture-focused cruises are a highlight, most visitors come in search of one particular building: the iconic Willis Tower. Formerly known as the Sears Tower, its 110 floors make it the tallest building in both North America and the Western Hemisphere. In search of the best city views, I find myself riding its ear-popping elevators to the 103rd floor later that afternoon. Here the Skydeck Chicago offers unforgettable views of the city and Lake Michigan. If you’re brave, take a step into “The Ledge”, a glass cube that juts out a metre beyond the edge of the building, offering gut-wrenching views to the pavement nearly 305m below. Across town, the John Hancock Tower offers similar sky-high views.
Walking the city
The two towers bookend the downtown district of Chicago, linked by the inner district known as The Loop, and the city’s famed “Magnificent Mile”. The Mile is a fine place to stretch your legs after a long flight, and during my days in Chicago I walk its length many times, from the historic water tower in the north to the museums and parks of the south. If you fancy a diversion, head east to Navy Pier. Built in 1916 to accommodate the boom in lake shipping, it’s been rejuvenated into a kilometre-long arcade of restaurants, shops, amusement parks and gardens.
But I wander south towards Millennium Park, a 10ha slice of public land that borders Lake Michigan. And it’s a rare tourist that doesn’t end up here. Apart from the charming open space and views of the city skyline, you’ll find throngs of tourists taking quirky selfies in the public artwork affectionately known as “The Bean”.
Created by British architect Anish Kapoor, “Cloudgate” – to give it its official name – is a remarkable work; a 100-ton puddle of polished steel that reflects and distorts the city skyline. Inspired by the flow and quiver of liquid mercury, it’s an otherworldly piece of public art that’s impossible not to love.
It’s the first piece of art and design that graces Millennium Park. A short walk from The Bean is the eye-catching Jay Pritzker Pavilion. Here the latticework roof and striking auditorium designed by Frank Gehry plays host to open-air concerts throughout summer. In winter, the nearby McCormick Tribune Ice Rink is the place to lace up your skates.
Worth a visit at any time of year though is the Art Institute of Chicago. In a gallery space that combines both classical and modern elements, more than 300 000 works – the third-largest art collection in the USA – cover everything from classical sculpture to modern multimedia installations.
Although the Institute is home to the largest collection of Impressionist works outside the Louvre, I loved discovering the iconic American art on display: the likes of Grant Wood’s “American Gothic” and Edward Hopper’s broody “Nighthawks”. Alongside the permanent collection you’ll find a number of temporary exhibits. In 2016 that included the imaginative dream-inspired works of South African artist Kemang Wa Lehulere, the Cape Town artist’s inaugural showing in the USA. Across town, the Museum of Contemporary Art (MCA), with its focus on international and American artists producing works after 1945, is equally worth a visit.
Beyond the world of art, the city’s cultural landscape ranges far and wide. The Field Museum is a treasure trove of natural history artefacts, and has graced the shores of Lake Michigan since 1893. A short walk away is the Shedd Aquarium, with exhibits ranging from the Great lakes ecosystems to the Caribbean reefs, while the nearby Adler Planetarium is another great option for travellers with kids. And, if you can get tickets, Soldier Field stadium around the corner is home to the much-loved Chicago Bears American Football team.
I don’t have time for a game on my visit though. By now the sun is dipping and my stomach’s grumbling.
When it comes to finding dinner in the Windy City, first-time visitors really only have one choice: deep-dish pizza. A meal as inherently Chicagoan as the Cubs baseball team, deep-dish typically involves a thick pastry-like crust filled with an inverted layering of cheese, sausage and chunky tomato sauce.
Although its exact origins are disputed, local lore has it that the deep-dish was invented at Pizzeria Uno back in 1943 with the owners Ike Sewell and Ric Riccardo looking to offer a uniquely Chicagoan pizza. They succeeded, and today deep-dish pizza can be found at hundreds of restaurants across the city as locals and visitors fill up on this hearty all-American staple.
Locals will argue fervently over who bakes the best deep-dish in the city. Gino’s East is a top contender, with a craft brewery on site to help wash down their signature dish: the “Chi-talian Stallion” of Italian beef, roasted sweet peppers and giardiniera pickles. In the end I opt for Lou Malnati’s, another iconic Chicago outlet that’s been dishing ’em up since 1971.
While a deep-dish pizza is an indelible part of Chicago’s culinary heritage, it’s not the only gourmet attraction the city has to offer. While you’ll find great restaurants spread across the sprawling suburbs, in the downtown district it’s Randolph Street you’ll want to explore.
There’s good reason this boulevard in the city’s West Loop is dubbed Restaurant Row, with dozens of eateries offering up everything from Asian-fusion to modern American cuisine. If you’ve had enough of deep-dish pizza, this is the place to head for.
South of The Loop, Chicago’s bustling Chinatown is a worthwhile diversion. Aside from discovering the wonderful Cantonese restaurants, don’t miss a stop at the Chinese American Museum of Chicago that celebrates Chinese history and culture in America.
There’s history and culture on every corner in Chicago, but not all of it is at ground level. As you wander the pavements of the Windy City, don’t forget to look up and admire the city’s history written in its skyline.
Text by Richard Holmes.