Gabe Fries from Bobby’s Bike Hike Chicago on the best pizza in the city.
Stephanie Holmes takes a deep breath and steps into a glass box suspended 412m above the streets of Chicago
Sage advice when suspended in a glass box 103 storeys above ground would be "don't look down". But on this 5cm thick, clear platform, 412m in the air, I can't tear my eyes away from the Chicago city streets far below me. Not a wobble in my legs, a butterfly in my stomach or a clammy palm can stop me — the view is captivating, the experience exhilarating.
The early morning fog slowly burns off, revealing a brilliant blue sky and the overwhelming mass of Lake Michigan, rippling in the breeze of this early winter's day.
From ground level, the lake is monstrous, easily fooling onlookers that it's actually a coastline. But from the vantage point of the Ledge at Skydeck Chicago, a fully clear day reveals shores of the four US states that surround it; Illinois, Wisconsin, Indiana and Michigan.
The Ledge is an award-winning attraction at Chicago's Willis Tower (formerly known as the Sears Tower), the second tallest building in the Western Hemisphere and the 16th tallest building in the world. Opened in 1973, the building's viewing level, Skydeck, followed the year after and was instantly a hit with locals and tourists, who flocked to the 103rd floor to get a bird's eye view of the Windy City.
But the forehead prints left on the glass at the end of each day suggested that people wanted something more. Remember that scene in Ferris Bueller's Day Off, when Ferris and friends stand on the railings and press their heads against the glass, looking at the city below them? Well, it was this, and the many visitors who also strained to get a better view, that inspired the Ledge — four glass boxes protruding 1.3m from the building, giving unobstructed views to the ground and the chance to feel like you're suspended mid-air.
The view from The Ledge. Photo / Stephanie Holmes
They also give incredible photo opportunities — I come away with multiple photos of my feet, the view, and my friends in adjacent boxes. It's the latter that gives the best perspective of this feat of engineering ... and causes those with even the slightest hint of vertigo to shudder on viewing.
My senses are challenged from the moment I arrive in Chicago. Flying west from Boston, an unseasonal Arctic blast blows in with us and although still early November, the temperature is down to -4C.
As much as I protest that this is no weather for cycling, Chicagoans are clearly hardier souls — our guide, Gabe from Bobby's Bike Hike, is raring to go, ready to lead us around some of the city's best spots on a Bikes, Bites and Brews Tour. Wearing fleece tights, wool socks, jeans, a T-shirt, merino jumper, wool coat, blanket scarf, leather gloves and thick beanie, I still have never been as cold in my life as I am when riding alongside Lake Michigan. Even though it's "warmed up" to -2C, the wind chill from the lake means it feels more like -11C. Brrr.
Rugged up and ready to go. Photo / Stephanie Holmes
Cold aside, I would definitely agree with the Bobby's Bike Hike team that cycling is a great way to see — and taste — the best of the city. Unlike Auckland, drivers seem charmingly respectful of our group of 12, letting us take up a whole lane, giving way to let us cross at junctions and generally keeping a patient distance.
This tour, one of 12 offered by the company, takes in "Chicago's four favourite food groups" — pizza, hot dogs, cupcakes and beer.
After 20 minutes on our bikes through Downtown Chicago, we're at Lou Malnati's, a famous deep-dish pizza restaurant. Founder Malnati started out working in Chicago's first deep-dish pizzeria in the 1940s; on March 17, 1971, he opened his first restaurant in the predominantly Jewish suburb of Lincolnwood. "He always thought it was funny that an Italian should open a pizzeria in a Jewish neighbourhood on an Irish holiday," Lou Malnati's website reads. "But that was Lou's style."
Guide Gabe on a warmer day. Photo / Clayton Hauck for Choose Chicago
The formula worked — the restaurant grew to a chain (now with 50 restaurants across the greater Chicago area), and the pizza is regarded by many as the city's best.
Regular diners have to wait about 45 minutes for their pizzas — you can't hurry a recipe this great — but Gabe has ordered ahead and we are tucking into slices of deep-dish goodness, oozing with mozzarella, spinach and rich tomato sauce, almost faster than we can take off our gloves.
And before we've had time to wipe the crumbs from our mouths, Gabe has whipped us out the door, back on our bikes and pedalling to our next stop. There's definitely no time to work off the carbs though; soon we're at the bright-green door of Murphy's Red Hots, to wolf down a Chicago-style hot dog.
Deep dish pizza from Lou Malnati's, Chicago Photo / Stephanie Holmes
Chicagoans take their food seriously, and none more so than hot dogs. The previous night over dinner at 676, the restaurant at Omni Chicago Hotel, sales and marketing director David Katz had waxed lyrical about the city's best joints and the dos and don'ts for ordering. His most valuable piece of advice — don't ask for tomato sauce. It's a big no-no, with even former President and long-time Chicago resident Barack Obama quoted as saying "Once you're past 8 years old, ketchup does not belong on your hot dog."
Many hot dog restaurants don't even keep it in the building. You won't miss it though, thanks to the tasty Vienna Beef sausage inside (choosing restaurants that only use Vienna Beef is another must, says Katz), and the seven key ingredients on top: mustard, sweet relish, onion, tomato, a pickle, peppers and celery salt.
A true Chicago hot dog is "like a symphony of flavours", Gabe says. "Ketchup is like a big band — it just overpowers everything."
A hotdog at Murphy's Red Hot. Photo / Stephanie Holmes
The rest of the tour takes us through the diverse Gold Coast, Lincoln Park, Old Town and Lakeview neighbourhoods, with a stop at Wrigleyville, home to the famous Chicago Cubs baseball team.
The area has seen much regeneration since the Cubs won the World Series in 2016 after a 108-year drought, but for many locals it's always been a good place to live. Many of the apartment buildings and multi-level houses surrounding Wrigley Field have rows of bleachers on their roofs so residents and friends can watch the games without paying to get into the ground.
It seems good views are just a way of life for Chicagoans.
Checklist: Chicago
GETTING THERE
American Airlines flies from Auckland to Chicago, via LA, with return Economy Class fares from $1509, on sale until November 30.
