With Air New Zealand's new service about to head for the Windy City, Greg Fleming lists the must-see attractions.
There's plenty to see — and hear — in a city which was instrumental in the development of jazz, blues, rock n roll, hip-hop (Kanye and Chance the Rapper grew up here) and dance music. Head out to Buddy Guy's Legends club if blues is your thing – the legendary singer-guitarist might show up. For jazz, Andy's or the Green Mill. All offer great talent every night at reasonable prices. The Empty Bottle in Ukrainian Village is the spot to get up close to the latest in alt rock.
Take a guided tour of the legendary Chess Records in South Michigan Ave, where Muddy Waters, Little Walter and Chuck Berry recorded, and which is to reopen as a working recording studio later this year. Rumoured first clients: The Rolling Stones.
Or time your visit for a music event: the Chicago Blues Festival in June, the Jazz Festival or the cutting-edge Lollapalooza rock festival at Grant Park, both in August.
There's plenty to do in the city centre but get out of town and sample the 77 neighbourhoods, each offering a different experience.
Pilsen is a vibrant, mainly Mexican district. As well as some architecture predating the 1871 Great Fire, it offers some of the city's best and most affordable Mexican food and politically driven street art.
If it's trendy stores and independent art galleries you're after, head to Wicker Park/Bucktown.
Explore Hyde Park, an upmarket, lakefront neighbourhood where Barack Obama has a home (although he currently lives in DC), for beautiful parks, museums and amazing Frank Lloyd Wright architecture.
If food's your thing, you've come to the right city. From fine-dining at the three-Michelin star Alinea or Oriole to the many trendy restaurants in Fulton St Market (try Duck Duck Goat) or the best in comfort and fast food (try the barbecue at Smoque), you'll never go hungry, so bring a big appetite.
You can't walk a block without a place offering deep-dish pizza or a classic Chicago hot dog — and don't forget the city's Italian beef sandwiches, the dark horse of the city's classic dishes.
If you're visiting in January, you can enjoy Restaurant Week when hundreds of eateries offer specially priced menus.
But whatever you do, don't put ketchup on your hot dog. Them's the rules.
Baseball, football, basketball and ice hockey are kings in Chicago. Catch a game at Wrigley Field, home of the Cubs baseball team. Even if baseball isn't your game, it's an unforgettable experience.
Soldier Field is home to NFL's Chicago Bears, a team which has a lot to prove after disappointing results in recent years. You can rely on their fans remaining loyal, no matter what.
Here's an example of how seriously Chicagoans take their sports. When the Blackhawks hockey squad's winning puck went missing after their 2010 Stanley Cup win, the Chicago FBI was called in to investigate. And no, it hasn't been seen since.
No other US city offers architecture on such a grand scale. The fire means many buildings date from the late 19th and early 20th centuries, a heady time in design and construction. Result: incredible heritage buildings stand alongside modern skyscrapers; look up from any street in the city centre and you'll be in awe. The best way to experience it is from the water: a cruise along the Chicago River or on Lake Michigan (both run from March to October). Walking architecture tours are also available.
If you're not scared of heights, catch the view from the 103rd floor of the Willis Tower.
6 The people
Chicagoans are a breed apart: loyal, tough, polite, hardworking and fiercely proud of their city.
They like to have fun too. When the Cubs finally won baseball's World Series in 2016, the city partied for days.
And you'll get great service in Chicago. Get used to being addressed as Sir or Ma'am and be ready to laugh; Chicagoans have a great sense of humour. A waiter who delivered room service one night told me it was no surprise the All Blacks lost to Ireland at Soldier Field — "those boys were partying and ordering hamburgers at 3am."
The US' third biggest city offers plenty of retail choices. Macy's, Saks Fifth Avenue, Nordstrom, all the usual suspects are here. If you can't find what you want on Michigan Ave's Magnificent Mile, it's probably not worth having.
Take the time to check out the gorgeous Tiffany vaulted ceiling at Macy's. Less frenetic is Oak St, home to Cos (H&M's high-end sister) and other fashion-forward offerings.
Where to start? There's great comedy (Second City), dance, opera and theatre. Chicago has its own Broadway (and it's a lot cheaper than New York's), with shows playing in five historic downtown theatres.
If more experimental fare is your thing, check out the Steppenwolf Theatre Company or The Yard at Chicago Shakespeare, which you'll find at Navy Pier.
In February, the city's theatres are more accessible than ever with discounted tickets to more than 120 shows.
The Art Institute of Chicago is another must-visit. Its permanent collection includes Picasso, Monet, Seurat, Edward Hopper, Georgia O'Keeffe and Andy Warhol.
9 The Water
Lake Michigan and the Chicago River set this city apart, offering a welcome respite from the energy of the city and a perfect platform to showcase its beauty.
The lake presents an unparalleled shoreline of beaches in the summer, while the river has recently been getting attention from outgoing mayor Rahm Emanuel. The River Walk has been extended, creating a series of connected pathways along its shore, perfect for a relaxing stroll. The more adventurous can sign up for a kayak tour.
10 It's easy to get to
From November 30, Air New Zealand will fly direct three times a week from Auckland, opening America's heartland to Kiwi and Aussie visitors.