Essential guide to Chicago

The new, independent Elysian (11 East Walton Street, 646 1300, www.elysianhotels.com, from $US360) combines exceptional service that isn't gratingly tip-oriented with smart accommodation. In-suite fireplaces and ultra-controllable mood lighting are just hors d'oeuvres. The Trump International Hotel (401 North Wabash Avenue, 588 8000, www.trumpchicagohotel.com, from $US445) screams "status": the enormous rooms have TVs in the bathroom mirrors, proper kitchen facilities and floor-to-ceiling windows. Meanwhile, the Peninsula (108 East Superior Street, 337 2888, www.peninsula.com, from $US575) is a sprawling expanse of marble; it's the sort of place where everything is just so, Mikimoto pearls are on display and a man is employed to push the revolving door for you.

Chicago hotels almost always quote prices without sales tax. Prepare to add 15.39 per cent to any price listed above.

* add +1 to call from Australia (see panel below).

SHOP + PLAY

To market

Chicago isn't much of a market city but the Randolph Street Market (1350 West Randolph Street, www.randolphstreetmarket.com) hosts regular events on the last weekend of the month between May and September. The popular Antique Market (www.chicagoantiquemarket.com) will run alongside the Indie Designer Market (www.indiedesignermarket.com), for example — handy for those who like to pick up their old clocks and new threads at the same time. For food, the Green City Market (www.chicagogreencitymarket.com) runs between 8am and 1pm every Wednesday and Saturday. In summer, it takes place outdoors at the southern end of Lincoln Park. In winter, it moves inside the Peggy Notebaert Nature Museum (2430 North Cannon Drive).

Go shop

The stretch of North Michigan Avenue between the Chicago River and Water Tower Place isn't known as the Magnificent Mile for nothing. It's home to just about every high temple of consumerism you can think of, including massive Disney, Apple, Cartier and Saks Fifth Avenue stores. For something a little less corporate, the Wicker Park area has a number of cool, indie clothing and accessories outlets, plus specialist bookstores and record stores. The junction of Damen, North and Milwaukee avenues is the best area. For gifts, the Chicago Architecture Foundation's shop (224 South Michigan Avenue) is fantastic — expect everything from The Scream ice-cube makers to skyscraper Lego.

Live music

Chicago is the birthplace of the electric blues and the spirit of Muddy Waters is still channelled at a number of clubs across the city. Buddy Guy's Legends (700 South Wabash Avenue, 427 1190, www.buddyguys.com) pulls in some of the biggest names and Guy himself takes to the stage every now and then. For jazz, the amazing wood-panelled Green Mill (4802 North Broadway Avenue, 773 878 5552*, www.greenmilljazz.com) has the atmosphere, as well as high-quality musicians and a reverent audience. If indie rock is more your thing, then The Empty Bottle (1035 North Western Avenue, 773 276 3600*, www.emptybottle.com) is the top spot.

Nightclubs

Chicago also gave the world house music and Spy Bar (646 North Franklin Street, 337 2191, www.spybarchicago.com) does it beautifully. It has less attitude (particularly from the door staff) than many of its rivals and consistently pulls in big-name DJs. The Funky Buddha Lounge (728 West Grand Avenue, 666 1695, www.funkybuddha.com) concentrates on hip-hop and reggae and you'll share the dance floor with a pleasingly mixed crowd. Meanwhile, the music policy at the Debonair Social Club (1575 North Milwaukee Avenue, 773 227 7990*, www.debonairsocialclub.com) veers all over the place but the party vibe, video art and cool lighting effects make it a fun hangout.

SEE + DO

Icons

The Chicago skyline is arguably the most incredible on Earth and while the skyscrapers are probably best explored from the ground, two of the city's most famous buildings have observation decks. The one at the John Hancock Centre (875 North Michigan Avenue, 751 3681, www.hancockobservatory.com, $US15) offers better perspectives than its higher rival at the Willis Tower (formerly the Sears Tower, pictured below, 233 South Wacker Drive, 866 512 6326*, www.theskydeck.com, $US15.95). Distorted views are also reflected in Anish Kapoor's Cloud Gate sculpture, one of the big-draw artworks in the superb Millennium Park. Less swanky and modern, but equally loved, is Chicago's elevated train network, the El. Take a ride.

Culture

Chicago has a number of legendary comedy clubs. The daddy — which boasts alumni such as Tina Fey and Steve Carell — is the Second City (1616 North Wells Street, 337 3992, www.secondcity.com). Visit for improv showdowns and revues. It's not all about the laughs, however; the city has a world-class theatre scene, too. The Steppenwolf Theatre Company (1650 North Halsted Street, 335 1650, www.steppenwolf.org) has an impeccable pedigree — this is where John Malkovich and Gary Sinise, for example, came through the ranks — plus a good mix of old favourites and challenging contemporary productions. For art, a number of good commercial galleries congregate around West Superior Street in the River North district.

Footwork

Many of Chicago's top attractions — such as The Field Museum, Adler Planetarium and Shedd Aquarium — are on the south side of Grant Park. If coming from the city, there's an obvious and enjoyable walking route to them through Millennium and Grant parks. Further north, try heading through upmarket Lincoln Park, then keep on going towards Canada along the Lake Shore Trail, which hugs Lake Michigan. For a guided walk, the Chicago Architecture Foundation (922 3432, caf.architecture.org) organises traipses through the skyscrapers, pointing out design flourishes and bits of history that you probably wouldn't otherwise notice.

Follow the leader

The Chicago Architecture Foundation also offers $US32 cruises along the Chicago River that explain the story behind the city's most impressive buildings. To come to grips with the city beyond the obvious highlights, Chicago Neighbourhood Tours (742 1190, www.chicagoneighborhoodtours.com, $US30) offers guided ventures into areas of the city, sampling everything from churches and cemeteries to murals and Mexican bakeries. To uncover the city Chicago's powers would like you to forget about, try the Untouchable Tour (773 881 1195*, www.gangstertour.com, $US28). It's a comedy romp through the key spots of the Al Capone gangland era.

EAT + DRINK

Cafe culture

The West Egg Cafe (620 North Fairbanks Court, 280 8366) will do your eggs any way you can imagine — and plenty that you can't. Gourmet pancakes, waffles, salads, sandwiches and juices are also for those who just can't decide. The Wicker Park neighbourhood is the best bet for cafe-based mooching, however. Rodan (1530 North Milwaukee Avenue, 276 7036, www.rodanchicago.com) is a little too cool for school but the stylishly minimalist decor, small plate dishes and good coffee work. Across the road, the Earwax Cafe (1561 North Milwaukee Avenue, 773 772 4019*) has a grungier vibe — expect circus murals on the walls and freak-show paintings to go with your herbal tea or fruit smoothie.

Snack attack

The seventh-floor food court in Macy's Department Store might not seem a particularly fruitful hunting ground but that's where to find Frontera Fresco (111 North State Street, 781 4884). It's the ready-to-go offshoot of celebrity chef Rick Bayless's Frontera restaurant and does mean quesadillas, huaraches and tortas. Meanwhile, the canteen-style cafeteria at gourmet food store Fox and Obel (401 East Illinois Street, 410 7301, www.fox-obel.com) serves soups and boxed meals of a fittingly high standard. For the sweet tooth, Canady le Chocolatier (824 South Wabash Avenue, 212 1270) glitters with diet-threateningly good chocolates, gelati, cakes and cookies.

Top of the town

Alinea (1723 North Halsted Street, 867 0110, www.alinea-restaurant.com) is frequently rated one of the best restaurants in the world. Its molecular-gastronomy pioneer, Grant Achatz, is often compared with Spanish super-chef, Ferran Adria, and tables need reserving well in advance. If you can't get in, try Charlie Trotter's (816 West Armitage Avenue, 773 248 6228, www.charlietrotters.com), where the $US165 grand tasting menu delves through the finest ingredients from across the world. Spiaggia (980 North Michigan Avenue, 280 2750, www.spiaggiarestaurant.com) meanwhile, does an unquestionably classy take on fine Italian cuisine. It's an Obama favourite when the president is in town.

By the glass

The dark but wonderful Clark Street Ale House (742 North Clark Street, 642 9253) is the perfect place for sitting at the bar, ploughing through the enormous selection of beers on tap and chatting to your new friend on the stool next to you. If you prefer to experiment with wine rather than beer, the Bin Wine Cafe (1559 North Milwaukee Avenue, 486 2233, www.binwinecafe.com) in Wicker Park offers themed "flights" of wine — four generous tastings of deliberately matched wines to sample in order. For cocktails, C-View on the 29th-floor rooftop at the Affinia Hotel (166 East Superior Street, 523 0923, www.affinia.com) conjures a laid-back vibe with great views.

Hot tip

While the Loop — as downtown Chicago is invariably known — has most of the stunning architecture, the city's personality comes from its distinctive neighbourhoods. You can experience a very different feel just by moving a few blocks along and there are a few intriguing ethnic enclaves. Ukrainian Village, Little Italy and Chinatown speak for themselves; Pilsen has an artsy Mexican vibe and Andersonville has maintained its Swedish heart.

Getting there

The cheapest flights to Chicago involve changing planes in Los Angeles. Return fares can be found for about $1500 upwards and it's worth shopping around with such carriers as United (www.united.com), V Australia (www.vaustralia.com.au) and Qantas (www.qantas.com.au) for the best price.

Visas and currency

Australians don't need a visa to enter the US but it is mandatory to go through the Electronic System for Travel Authorisation. You can fill in the paperwork at https://esta.cbp.dhs.gov and hand over the requisite $14 at least 72 hours before travel or they're probably not going to let you in. Currency is the US dollar — $US1 = 99.7¢.

Calling Chicago

Add +1 (the international code) then 312 (the Chicago dialling code) to any of the seven-digit numbers listed above if calling from Australia. For those numbers marked with an asterisk, just add +1.

More information

www.explorechicago.org.

The writer was a guest of the City of Chicago.