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The city that gave us deep dish pizza, skyscrapers, Al Capone and broody back-alley bars for blues and jazz music, Chicago offers more than you ever imagined.   


1. Eat

Deep dish pizza-pies guaranteed to make your doctor wince, the XL pizza was born in Chicago. Famed pizzerias include Gino's East, Lou Malnati's and Giordano's, but cult fave, Pequod’s is your go-to for low-key authenticity. Seven inches of dough and caramelised crusts ensure a knockout experience. Or you could try Anthony Bourdain’s preferred pizzeria, Bonci, hailing from Italy. The pizza’s served in rectangles and sold by weight – just like Naples. 

2. Drink

It’s been 85 years since the end of Prohibition, so drink up! Chicago’s swarming with cool speakeasys, such as Spilt Milk Tavern, a former-pharmacy turned classic corner bar. Then there's Chicago Riverwalk which has been revamped and is now teeming with achingly hip hangouts like City Winery. For cool hangouts, Celeste Chicago on Hubbard Street, covers four floors of eclectic happenings. There’s a 1920s themed bar, live music and a rooftop honky-tonk with Victorian aesthetics. 

3. Shop

Fast fact: Before opening his store in London, Gordon Selfridge (of Selfridges' fame) learned his trade in Chicago. Yup, this city’s a mecca for shopaholics. Magnificent Mile (AKA Mag Mile) lives up to its name, especially if you’re in need of a US shopping spree. Between the upmarket hotels and posh nosh, 460 retailers invite you – and your plastic – through their doors. From upscale shops to luxe fashion outlets, it’s like a mini New York with all the big city goodies, such as Bloomingdale's, Saks Fifth Avenue and Macy's. 

4. Admire

The world’s first skyscraper was built in Chicago (the 10-storey Home Insurance Company on the north-west corner of LaSalle and Adams Street) and it’s a city well regarded for taking architectural risks. After the great fire wiped out 17,500 buildings in 1871, Chicago changed the face of architecture forever. Get lost in the city's streets and absorb its innovative design.

5. Listen

Sure, the blues get bluer the further south you travel, but it was when all said and done, the Mississippi Delta and all those who hitchhiked along it that brought the art form north. Chicago will always be a blues’ town. The legendary Green Mill is where Al Capone sat and absorbed his city’s acoustic talent. Ask about his favourite booth or go in search for tell-tale bullet holes in the wall. From blues to jazz, to swing and rock n’ roll, the live music is legendary.

6. Snack

At the first-ever Nutella Cafe. Loosen your waist belt and gorge on waffles and crepes slathered with this deliciously devilish spread. Open until 9pm (hello dessert!) find it at 189 N Michigan Ave.

7. Find


Take in the magic of the American Girl Store, a doll company, come toy company, come PG pink-flushed wonderland. With two levels of dolls and their accessories, there’s even a hair salon where your kid’s favourite doll can get a brand new do. If dolls aren't your sprogs 'thang', The Field Museum of Natural History is one of the world’s largest and home to a massive Tyrannosaurus rex skeleton named Sue.

8. Learn


Home to both the country’s largest science museum (MSI) and the world’s biggest indoor aquarium (the Shedd) Chicago’s egghead scene is comprehensive. The MSI is hugely interactive and houses a mammoth World War II German submarine. If you’re in the city in January, February or September, these are the months with the most free-admission days. Hurrah! British sculptor Anish Kapoor’s infamous Cloud Gate is the must-see outdoor art installation, and the Art Institute of Chicago is brimming with global art pieces.

9. Transit


Chicago is the second busiest airport in the world. Also making it one of the greatest hubs for getting around – both domestically and internationally. From Chicago you could easily hop to NYC, Boston and Philadelphia, or if you’re Europe bound, how about making Chicago your stopover?

10. See


The city’s world-class theatre scene is both historic and unmissable. With such a prolific background, celebs swarm here to perform, direct or become a founder. Gary Sinise (of "Lutenant Daaaaan!" And Forest Gump fame) is a founder of Lincoln Park’s Steppenwolf Theatre Company, while Ross from Friends – professionally known as David Schwimmer - is the co-founder of the Lookingglass Theatre Company on Magnificent Mile. In 2018 he directed the world premiere of Plantation!

11. History


It wouldn't be proper to visit Chicago and not take a gangster tour. Ask us about daily availability and delve into Chicago's grittier past. 

Let's go to Chicago! These dollar-saving Our USA deals will sort you right out. Better yet, come in-store and chat with one of our friendly travel experts. We love pairing Kiwis with their perfect holidays!



Jump on a direct flight from Auckland to Chicago O’Hare International Airport with Air New Zealand, taking approx. 15 hours northbound, and just over 16 hours southbound.


Mid-spring to mid-autumn (April-October) is the best time to visit. Winters are cold but also magical. When the snow settles and the skyline is aglow with lights you'll want to wrap up warm and venture out for steaming hot chocolate.


O’Hare International Airport. Roughly US$35-40 for a metred taxi to downtown Chicago taking approx. 60-minutes. However, this city’s busy so it can take longer.


The subway is referred to as ‘The L’. Uber is readily available.



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