24 hours in Chicago

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This was published 14 years ago

24 hours in Chicago

Wow factor ... Navy Pier and the city's soaring skyline.

Wow factor ... Navy Pier and the city's soaring skyline.Credit: City of Chicago

There is big, brash Chicago - the soaring architecture, grand boulevards and dazzling location on a glassy lake. Yet to read this city's soul, one must escape downtown for subtler pleasures. The sway of a late-night saxophone. Hoots and heckles at a comedy club. The simple joy of discovering a dive bar, or delicious, dirt-cheap Mexican food on an otherwise ramshackle strip. This sprawling metropolis - America's third-largest - is not the easiest to navigate. But if you get lost, a cheerful midwesterner will help. Avoid the worst of the weather by arriving between April and October.

8am

Roll out of bed and hail a cab to Milk & Honey, in fashionable, grungy Ukrainian Village, for one of Chicago's best breakfasts. Sit outside and watch the city rumble to life as you tuck into buttermilk-granola pancakes or orange brioche french toast. Then work it off by exploring the boutiques and thrift shops along the hipster triangle formed by Milwaukee Avenue, Division and Damen streets.

Milk & Honey, 1920 W Division Street, milkandhoneycafe.com.

10am

Catch the "El" train downtown - so named because of the screeching, Gothic-style elevated track that snakes behind the bedrooms of apartment residents. It's time to get a handle on Chicago's monstrous dimensions by climbing the Sears Tower (recently renamed Willis Tower). An innovation is the "Ledge", a glass balcony that juts unnervingly nearly two metres off the 103rd floor. Say a prayer and tiptoe forward - you'll feel like you're floating. For equally jaw-dropping views but shorter queues, try the John Hancock Centre.

Sears Tower, 233 S Wacker Drive, theskydeck.com. John Hancock Centre, 875 N Michigan Avenue, www.hancock-observatory.com.

11.30am

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Michigan Avenue is Chicago's Champs-Elysees. Treats include Millennium Park and the futuristic steel sculpture known as "the Bean". Dip your toes in the Crown Fountain, another quirky artwork in which the faces of ordinary Chicagoans are projected from two towers as water gushes out. Then head up to the world-renowned Art Institute of Chicago. Time is precious so limit your focus - milk every last drop from the Modern Collection (highlighted by Magritte's Time Transfixed and Picasso's The Old Guitarist) and the Pritzker Galleries, an Impressionist treasure trove. You could spend 24 hours in the art institute alone.

Art Institute of Chicago, open daily, adults $US18, ($19.70) 111 S Michigan Avenue, artic.edu.

2.30pm

Grab a double cheeseburger and side of pickle chips at the Billy Goat Tavern hole-in-the-wall. Then push off the Michigan Avenue Bridge for an architectural boat tour. Chicago's mesmerising and unusual skyline - featuring three of America's five tallest buildings - ascended from a prairie swamp after the 1871 Great Fire. With the city encircled by water, there was nowhere to go but up, and the imagination of architectural visionaries such as Louis Sullivan and Daniel Burnham ensured far more than a drab collection of concrete.

Billy Goat Tavern, 430 N Michigan Avenue, billygoattavern.com. Chicago Architecture Foundation River Cruise, ticket information at architecture.org.

4pm

Stroll down the Magnificent Mile - Chicago's high-end shopping strip - then duck right on Illinois Street until you hit Bobby's Bike Hike. There's no better way to unwind than by cycling Chicago's lakefront. But in which direction? If north, pedal past the tourist amusements at Navy Pier, along Oak Street Beach and up to Wrigley Field, home of the Cubs baseball team.

For dinner, order a deep-dish pizza: a Chicago specialty with steep, buttery crusts cushioning a lather of toppings and cheese. Many swear Lou Malnati's in River North is the best.

An alternative: take the quieter southward trail and cycle to Hyde Park. This is a leafy, mixed-race neighbourhood and home to the beautiful University of Chicago campus and some great bookshops. Gawk at President Obama's house on the corner of 51st Street and Greenwood Avenue.

Then pull into Calypso Cafe for a hearty Caribbean dinner of plantain nachos, seafood cakes and jerk chicken. When you've finished, clamp your bike to the front of a bus for the ride back.

Bobby's Bike Hike, 465 N McClurg Court, bobbysbikehike.com. Lou Malnati's Pizzeria, 439 N Wells Street, loumalnatis.com. Calypso Cafe, 5211 S Harper Avenue, calypsocafechicago.com.

9pm

Throw on a change of clothes and catch the northbound Red Line train to Lawrence. Jazz shows at the legendary Green Mill begin at 9pm, but you'll need to arrive early to guarantee a seat.

It's a dark, intimate, 1920s-style venue that used to be frequented by Al Capone. A few gin martinis and you'll soon be eyeing the dance floor. The Sunday night poetry slams are particularly good sport.

Green Mill Jazz Club, 4802 N Broadway Avenue, greenmilljazz.com.

11.30pm

Finish with a late-night club-hop through Wicker Park's hidden gems, pausing for a hot fudge sundae before Margie's shuts at midnight. Danny's is stylish without being pretentious, with plenty of dimly lit crevices making it perfect for a cuddle or chat. Last stop is the Hideout (open until 2 or 3am), a pumping garage space that spills onto an industrial lot.

Sip your beer out the front and wonder at the skyscraper-silhouetted wasteland - old and new Chicago, all out under the stars - and where you fit among it all.

Margie's Candies, 1960 N Western Avenue, +1 773 384 1035. Danny's Tavern, 1951 W Dickens Avenue, +1 773 489 6457. Hideout, 1354 W Wabansia Avenue, +1 773 227 4433.

United Airlines flies nonstop from Sydney to Los Angeles (13hr 30min), where you change aircraft and clear immigration and customs, then to Chicago (4hr). Melbourne passengers transit in Sydney. The fare is about $1355 low-season return from Melbourne and Sydney, including tax. Australians must apply for US travel authorisation before departure on the secure website https://esta.cbp.dhs.gov.

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