Blustering through a tour of the Windy City's most famous skyscrapers
Move over NYC, this US city has history, blues, comedy, big food, big buildings and avid sports fans. Chicago can do no wrong, writes Sam Hurley.
They say Chicago is the most American experience of the big United States cities.
It has a pioneering history, architecture that reaches for the sky, blues, comedy, big food and rabid sports fans.
The metropolis of nearly 10 million people sits on the shoreline of Lake Michigan, which you could be forgiven for thinking is a sea given its vastness, sandy beaches and sailboats. The size of the Great Lakes has even given rise to it being referred to as America’s Third Coast.
As a visitor, it’s hard to walk around the city without gazing out to the lake or being told of how the Great Chicago Fire shaped the streets and global city it is today. After the destruction of 1871, a booming economy and rapid population growth followed as Chicago became the birthplace of modern architecture and the skyscraper. Architects from the world over flocked to the Midwest to rebuild.
Every local seems to have an opinion on what started the fire too, the most popular, but somewhat debunked folk story, blames Mrs O’Leary’s cow which allegedly knocked over a lantern.
The Chicago World’s Fair in 1893 followed and the city never looked back. Today, the architecture of past and present continues to play a proud part in the city and its people’s lives. Not far from Neo-Gothic Tribune Tower are innovative modern designs such as the Wanda Vista Tower and its curvy illusion - the world’s tallest structure designed by a woman.
The Chicago River is a great place to view the city's architecture from. Photo / Sam Hurley
For all the steel and stone beauty these buildings hold, and as someone who isn’t the biggest fan of heights, going up one of these super-tall buildings isn’t my idea of a relaxing morning. Yet being at the top of the tallest one, the Willis Tower, is breathtaking.
Opened in 1973 as the world’s tallest building, a title it held for nearly 25 years, you can - on a clear day - see four states. Wisconsin to the north, Indiana to the south, Michigan across the lake and Illinois where it stands.
The Sears Tower, the original name locals still prefer to use, tops out at 527m. For comparison, Auckland’s Sky Tower feels like a diminutive328m to the top of its antenna.
For those who have watched Ferris Bueller’s Day Off, you can stand at the exact spot where the trio of teens press their heads against the glass and stare down to the streets below. Now you don’t have to squish your face against the glass like Ferris thanks to The Ledge, a series of glass boxes some 412m in the air that jut out from the Skydeck giving you unobstructed, yet nauseating, views.
You’ll recognise many of the city’s famous landmarks from films such as The Dark Knight, The Blues Brothers, and one of my favourite Christmas movies, not Home Alone, but While You Were Sleeping, which uses Chicago’s iconic elevated rail network.
To experience the best views, an architecture cruise on the Chicago River is an absolute must-do. The First Lady Cruises offers a 90-minute, in-depth tour, while a portion of each cruise ticket supports education and exhibits provided by the Chicago Architecture Center.
The river, which gets dyed green for Saint Patrick’s Day, is a great place to spend time walking along or enjoying lunch at one of the many restaurants lining the water. Like many things in the city, it has a history, and because of a monumental feat of civil engineering in the late 1800s, it runs backwards and away from the lake.
Chicagoans told me they like to joke this was done to “take their s***” down the Mississippi River to St Louis, which shares a playful rivalry with Chicago that is best exemplified by the two cities’ baseball teams, the Cubs and Cardinals.
A Chicago Cubs v Pittsburgh Pirates baseball game. Photo / Sam Hurley
If, like me, you want to catch a game, then Wrigley Field and its ivy-covered brick walls, the US’ second-oldest baseball stadium, in the city’s north is where to go. If you have to wait for the game to begin because of a rain delay, then ask a fan about the Curse of the Billy Goat for a fun story.
The leafy neighbourhood Wrigley sits in, with its rooftop bleachers adorning nearby apartment buildings, is also filled with bars and things to eat before the game - like a classic Chicago-style hotdog.
A classic Chicago-style hotdog, with no ketchup. Photo / Sam Hurley
The city has become somewhat of a culinary destination with fine dining and new establishments opening, such as UMMO (delicious modern Italian), and more casual food spots on the city’s West Side. So, it can be said the locals take their food seriously, but in the case of the hotdog, maybe a little too seriously.
Wrigleyville Dogs hotdog stand on Chicago's North Side. Photo / Sam Hurley
To give you an idea, I was told Chicago has more hotdog joints than McDonald’s, Burger King and Wendy’s restaurants combined.
Another piece of advice when ordering one, do not ask for tomato sauce.
If you do, you might well be told to eat somewhere else. Long-time Chicago resident and former US president Barack Obama once explained in a stone-faced manner, “It’s not acceptable past the age of 8” to put ketchup on your hotdog.
Instead, these are the key ingredients: A Vienna beef sausage, mustard, sweet relish, onion, tomato, a pickle, peppers and celery salt.
Another traditional Chicago-origin plate is the deep-dish pizza, which, as the name suggests, uses a deep pan to cook the base which is filled with toppings. However, unlike your Neapolitan or New York slices of pizza, the cheese goes on the bottom and the sauce on top to prevent the cheese from being burned in the longer-than-usual cooking time.
The key to a good pie, as they say, is the quality of the sauce - rich and fresh.
Chicago is an incredibly easy city to walk and the same is said for cycling because of its dedicated bike paths and courteous drivers, at least compared to Auckland’s aggressiveness. So, a great way to hit some of the city’s best spots is to do a Bikes, Bites and Brews Tour with Bobby’s Bike Hike.
Ranked a top 20 food tour globally by Tripadvisor, you’ll start near Navy Pier before making your way through the historic neighbourhoods of the Gold Coast, Lincoln Park and Lake View. If you travel in October and early November, you’ll also enjoy the Autumn colours in this area.
We had some pizza, a hotdog and something sweet at the original Molly’s Cupcakes, which won the first season of Food Network’s TV show Cupcake Wars in 2009 with its peach cobbler flavour, before burning off those calories by riding back down the lakefront.
Chicago's neighbourhoods are picturesque and easy to walk. Photo / Sam Hurley
I also visited Art Smith’s southern-style Reunion restaurant on Navy Pier. If he’s around and you’ve got the time, Smith is all too willing to recite in a humorous way the many celebrities he has cooked for, including Princess Diana and as the personal chef to Oprah Winfrey.
For me, a comedy show is one of the best night’s out you can have and The Second City show was one of the best I’ve seen. The improv troupe has launched some well-known careers in comedy, such as local legend Bill Murray, Steve Carell, Tina Fey, Stephen Colbert, and Ryan Stiles and Colin Mochrie from Whose Line Is It Anyway?
'The Bean' in Chicago is considered the birthplace of modern architecture. Photo / Sawyer Bengtson; Unsplash
Sadly, access to the famous Chicago Cloud Gate sculpture, nicknamed The Bean for its shape, was limited when I visited due to maintenance on the surrounding plaza until next year. Despite this, the more than 120ha of downtown green space that is Grant Park, with Buckingham Fountain at its centre and several top museums is worth the visit alone.
Take an afternoon to explore the Art Institute of Chicago, which houses Picasso’s The Old Guitarist, Edward Hopper’s Nighthawks, and what is considered the most impressive collections of Impressionism outside of France, including dozens of works by Monet.
If high-end fashion is your thing, then Michigan Ave is Chicago’s answer to New York’s Fifth Ave or LA’s Rodeo Drive.
Chicago is also synonymous with Prohibition-era gangsters, the most famous of course being Al Capone. There are still nods to this time in history with hard-to-find speakeasies scattered around downtown and the suburbs.
And of course, there’s the live music. Kingston Mines in Lincoln Park is considered the oldest, continuously operating blues club in Chicago, but there are many others you can visit and invoke the spirit of Muddy Waters. The city also hosts the annual Lollapalooza four-day music festival in Grant Park.
As Sinatra sang about Chicago, you can bet your bottom dollar you’ll have some fun.
