Some people’s love affair with Chicago surpasses New York and when you hear them explain why, it’s hard not to be swayed. Chicago sits on the fingertip of Lake Michigan, one of the five Great Lakes, with a sweeping shore line that is best viewed from the 94th floor of the John Hancock Center – and preferably over a whisky with a rasher of smokey bacon standing in it.

But to get to the 360˚ Observation Deck for that sublime drink, a stroll down Magnificent Mile, aka Michigan Avenue, requires enough time to take advantage of the shopping on offer. The street is wide and flowers and trees are planted down the centre taking the edges off an otherwise business-like road lined with towering buildings and importance.

First-time visitors to Chicago should start, wearing good shopping shoes, where the Chicago River runs under N Michigan Avenue and stroll parallel to the lake, browsing (and purchasing) as you go.

You’ll find malls and street front stores, and you’ll also find Garrett Popcorn. Don’t be fooled thinking popcorn is just for the cinema! Garrett is an institution and their genius combination of cheese and caramel corn mixed into one big bag or bucket will leave your tastebuds in a state of astonishment. It really is so good that people get it freighted to them all over the world and international stores have popped open in Hong Kong, Japan, Korea, Malaysia, Singapore, Taiwan, Thailand and the UAE. If they open in New Zealand our waistlines will be ruined.

Chicago is famous for many things, but one is food. And specifically their unique style of deep dish pizza. This is where the rivalry with New York knows no bounds as the latter swear that pizza should have a thin, crispy crust and Chicagoans prefer to consume their entire daily intake of calories on a single slice of deep dish pizza. Deep dish pizza is great! It’s made back to front like a big tomatoey pie with the cheese on first and each slice is at least three centimetres thick. But talk to any local about their favourite pizza joint and you’ll get as many different answers, however a few that always make the list are Giordanos, Lou Malnati’s and Pequod.

Chicago also has culture and sculpture in spades and allowing time to walk through the ten-hectare Millennium Park is a must. This is where outdoor concerts and public events are held and the famous stainless steel “bean” is located. Officially named Cloud Gate, you’ll want to get your camera out and experiment with the reflections, before walking as close as you dare to the spitting fountains, then, if it’s cold enough in November, donning your ice skates for a twirl.

A great way to quickly get to know Chicago, or any city for that matter, is to take a tour. They have everything from food tours to gangster tours, architecture river cruises to walking tours for free with local volunteers as part of the Chicago Greeters program. Or buy a CityPASS and you’ll save over 50% on five top attractions.

But as the Kiwis who are lucky enough to be at Soldier Field will attest, there’s nothing quite like a live sports game in America. Watching Americans watching sport is a sport in itself! Wrigley Field is the famous baseball ground and home of the Cubs, the Blackhawks ice hockey team play at the United Center and the Bears football team play at Soldier Field.

But to see only all these sights and sites in the Loop (downtown) is merely to scratch a tiny corner of this great town. Once you leave you’re sure to be promising to return.

Have you ever been to Chicago? What were your highlights? Let us know in the comments below.