Greg Fleming visits the USA's third largest city, and finds it's his kind of town.

In this part of the world Chicago remains something of a mystery. It may be the third largest city in the US and one that has successfully transitioned from an industrial centre to a global metropolis, but its profile here has been overshadowed by flashier destinations on the East and West coasts.

Expect that to change when Air New Zealand begins a thrice-weekly direct service from Auckland in November. The city has won Time Out's Best City in the World award for the past two years — and Kanye West even named his third daughter after his hometown.

The cityscape streets. Photo / Getty Images
The cityscape streets. Photo / Getty Images

It's a resilient and strangely beautiful city that has survived fire, corruption and its beloved Cubs baseball team losing for 108 straight years before finally winning the World Series in 2016. Naturally, the party went on for days.


If you want it, Chicago's got it

My introduction to the Midwest's infamous hospitality came at the legendary Lou Mitchell's Diner.

This family-run eatery — right around the corner from the start of Route 66 — is a city institution and its long and varied menu of American diner classics is comfort food of a high order.

I was halfway through my plate of Italian sausage omelette — served with potato chips, coffee, and Greek toast smothered in butter, with a freshly squeezed grapefruit juice to wash it down — when Donna, the 80-year-old proprietor, informed her customers over the diner's intercom that a table of Kiwis and Australians were in the house. The place erupted in applause. Then, as if we needed it, we got ice-cream and Milk Duds, compliments of the house, as we left. It was 8am.

That's one end of the food culture in Chicago.

A few nights later I sat down at Alinea — chef Grant Achatz's three-Michelin star fine-dining restaurant. It's so exclusive that Justin Timberlake had trouble getting a table.

Eating here is a once-in-a-lifetime experience combining theatre, molecular gastronomy and amazing food with a cheeky sense of fun. Thankfully, they supply a written menu after dinner — because, despite the waiter's patient explanations, I had no idea what I was eating much of the time.

It's a restaurant that makes you think. What looks like ice-cream is actually a salad, what should be sweet is salty, then the fruit centrepiece on the table explodes in dry ice.


Our four-hour, 10-course tasting menu hit all the senses — food came accompanied by smoke and other sensory cues. There was even an edible helium-filled balloon on a string for dessert (much hilarity ensued).

Chicago's Elevated Train passes above. Photo / Getty Images
Chicago's Elevated Train passes above. Photo / Getty Images

One course involved olives and artichoke hearts fashioned to look like the bed of rocks they were served on. In the kitchen downstairs (where we went to consume one course) there were no less than 25 chefs, so consumed by their tasks they hardly noticed our intrusion.

On another night we enjoyed sophisticated Chinese food at the Peninsula Hotel's Shanghai Terrace, overlooking the lights of the Magnificent Mile shopping district. If the wallet's a little light, Uber to Chinatown's Qing Xiang Yuan Dumplings.

That's the beauty of Chicago. Whether it's fine-dining, forward-thinking fusion, modern takes on American classics or calorific comfort food, this city has it and does it like no other.

There's deep-dish pizza everywhere (more like a pizza pie than the pizza we're familiar with, best eaten with a knife and fork). Weirdly to our taste, it has tomato sauce on top, cheese below and a sweet cornflour crust.

The Peninsula Hotel. Photo / Greg Fleming
The Peninsula Hotel. Photo / Greg Fleming

Chicago-style hot dogs are iconic, and they have their own rules. Both the poppyseed bun and Vienna beef dog should be steamed, then topped with yellow mustard, chopped white onions, sweet pickle relish, a dill pickle spear, tomato slices, pickled sport peppers and a dash of celery salt. Definitely no ketchup!


My favourite local classic was the Italian sandwich. It's a beef sandwich of thinly sliced, seasoned roast beef, simmered and served on a long Italian-style roll with jus on the side. The sandwich dates from the 1930s and is available all over town, but Al's original store on Taylor St is the place to go.

A great spot to sample Chicago's comfort food is the recently opened Revival Food Hall on South Clark St, a large, industrial-chic foodcourt featuring many popular eateries. The originals are scattered throughout the city but here you'll find their offshoots under one roof.

Try Smoque for amazing barbecue — the Texas-style brisket with a thick Memphis sauce and a side of spiced baked beans was superb. I returned the next day to try Budlong's fried chicken sandwich after noting the long queue on my first visit. Another winner: the breaded chicken spiced with a blend of cayenne and habanero peppers, served in a brioche bun, best with a side of collard greens.

There's deep dish pizza everywhere in Chicago. Photo / Getty Images
There's deep dish pizza everywhere in Chicago. Photo / Getty Images

For a mid-price casual night out, head to the Fulton Market restaurant district. We hit celebrity chef Stephanie Izard's dimly lit Duck Duck Goat. Izard took out Top Chef season four but her buzzy Chinese restaurant, with great handmade noodles, doesn't take itself too seriously. Their Mapo tofu was worth the visit on its own.

Home of the Bean

Small mercies. Chicago's a great town for walking off some of that great food. It's flat and the grid structure is easy to navigate.


One of your first stops should be Millennium Park. One of many green spaces in the city, the 10ha park hosts free concerts and community events — a tai chi workout was in progress when I visited. Since 2006 it has been best known as the home of the Bean, the country's most recognisable piece of public art.

The Green Mill cocktail lounge in Chicago. Photo / Senor_codo, Flickr
The Green Mill cocktail lounge in Chicago. Photo / Senor_codo, Flickr

Designed by British artist Anish Kapoor, the sculpture consists of a seamless series of polished stainless steel plates and has become a selfie hotspot, its amorphous curves reflecting the viewer and the surrounding cityscape.

Nearby is the Crown Fountain with its Faces of Chicago sculpture, where gigantic LED screens reflect the city's cultural diversity. Bonus: it's a great spot to get cool in summer.

Temperatures topped 35C during my visit.


Delve further into that ethnic diversity by getting out of the city centre to some of the 77 neighbourhoods. Each offers a distinctive social and cultural history. Old Town, Lake View, Wicker Park, Logan Square and Oak Park (birthplace of Ernest Hemingway) have their individual stories and highlights.


I took a walking tour of Pilsen on the lower west side. Once a Bohemian community, it's been home to mainly Mexican immigrants since the 1960s. It's one of the few neighbourhoods that wasn't destroyed in the Chicago Fire of 1871, so it's possible to see some of the original 19th century homes.

The suburb is also known for its politically charged street art (around 450 murals are scattered throughout the area) and its many Mexican restaurants and bakeries.

If you visit, make time for the National Museum of Mexican Art (free entry), showcasing 3000 years of creativity from both sides of the border. Afterwards, drop into Taqueria Casa Del Pueblo for some of Chicago's best, no-nonsense Mexican food.

Sound of the city

For me, the highlight of the trip came late one night when 82-year-old blues legend Buddy Guy walked on stage at his club and treated the crowd to an extended version of Johnnie Taylor's Cheaper to Keep Her. Guy is one of the last living links to the great bluesmen who came north from the Mississippi Delta to Chicago in the 50s. Artists like Howlin Wolf, Muddy Waters and Little Walter created a louder, electric form of blues that in turn gave birth to rock'n roll. Seeing him in his element, and in such fine form, was a rare privilege.

A show by Buddy Walker was a highlight for the author. Photo / Getty Images
A show by Buddy Walker was a highlight for the author. Photo / Getty Images

Later I ventured out to 2120 South Michigan Ave to visit the original home of Chess Records, where blues greats including Buddy Guy recorded. It's now the home of the Blues Heaven Foundation, founded by the daughter of the late Willie Dixon, who racked up thousands of writing credits as well as playing bass on many seminal blues recordings.


Tours run most weekdays for $15. There's some great memorabilia and a winsome host, Jeanine, a jazz singer who knew many of the blues greats she talks about. When she played Etta James' "At Last", recorded in the room we were in, she started to tear up. "I miss Etta, she was one of the greats."

There were about 10 in my tour party all from outside the US. "We get people from all over," Jeanine said. "Lots of blues fans from Norway, the UK and Germany, but strangely enough we hardly ever get anyone from Chicago."

The good news is that this is set to become a working studio again later this year, with the first clients rumoured to be none other than the Rolling Stones, who immortalised the studio in their 1964 instrumental, 2120 South Michigan Avenue.

Today Chicago's reputation as a leading music city continues. Hip hop artists Kanye West and Chance the Rapper are both native sons, while alt-rock darlings Wilco also call the city home. And the annual Lollapalooza festival brings the best cutting-edge pop and rock artists to Grant Park each August.

Jazz too is alive and well in Chicago. I caught a Sunday night jam session at Andy's Jazz Bar, where trumpeter Pharez Whitted's quartet included veteran guitarist Bobby Broom. Time your trip right, and you can catch the famed Jazz Festival in August.

City scenes


On my last day in town I got a Ventra card and braved the L train — the elevated trains that clatter through the city every few minutes.

It's a cheap way to appreciate Chicago's energy as you rattle past. Shoppers heft bags over their shoulders as they wait at the crosswalk, delivery vans fight for parking space, an ambulance flies up Wabash Ave, a drummer on the corner performs for tips, tourists on a walking tour hold their phones skyward as a docent talks into their earpieces.

Jazz brunch at the Green Mill. Photo / Flickr, Eric Allix Rogers
Jazz brunch at the Green Mill. Photo / Flickr, Eric Allix Rogers

For a city that essentially rose out of the prairie 115-odd years ago, the transformation is astounding. Mark Twain's evaluation still holds: "It is hopeless for the occasional visitor to try to keep up with Chicago — she outgrows her prophesies faster than she can make them."

You might not be able to keep up but you can't help but leave Chicago as an optimist.

It's a city busy doing its own thing, where the much-repeated greeting, "Welcome to Chicago", is less a platitude than an invitation to take part in an unforgettable journey.

No — it's not really windy in the Windy City. New York and Boston are windier than Chicago. It's thought the nickname originated from the hot air blown out by the Midwest city's Chicago politicians.


One thing that Chicago doesn't do well is coffee. But there's a branch of New Zealand's Mojo coffee chain at 200 South Wacker St in the business district if you fancy a flat white made right. Go say hello.



Air New Zealand

starts its new service to Chicago on November 30. Economy Class one-way fares start from $1019.





has been voted the best hotel in Chicago and second-best in the US. And it's located at Water Tower Park on the Magnificent Mile, the city's premier shopping district.