If you feel like a trip to New York City and you've already experienced the undoubted delights of the Big Apple, I'd recommend that you pass it up and go the extra airmiles, opting instead for Chicago. There are several good reasons to do this. First, it's a lot cheaper; Chicago is one of the least expensive big cities to live in and you'll find your dirham will stretch a lot further here. Second, the people are much friendlier. New Yorkers, like Londoners, are not intrinsically colder than other citizens, they just live in an alienating metropolis that makes them blasé. While Chicago has the benefits of a big city, it's somehow kept a more relaxed and human touch, giving it the feel of a place much smaller. Third, that non-metropolitan vibe gives an experience still quintessentially American, rather than global. Chicago is also at least as easy on the eye; it's skyscrapers and architecture are as spectacular as New York's, although not as claustrophobic. Its neighbourhoods - at least the ones you'll be staying in or visiting - are much prettier, and at least as safe. At this point I should admit to a certain bias. My wife hails from Chicago, and I have lived here, on and off, for six years. I've taught creative writing to its university students and found the inspiration for a short story from my collection If You Liked School, You'll Love Work in the city. And, yes, I love it. Too long passed over between New York and LA, America's "Second City" is also its best kept secret, and Chicagoans, on the whole, are pretty damned happy with that. One important caveat: Chicago hibernates roughly between Halloween and St Patrick's Day, when the river is dyed green and the city springs to life. But it gets so cold in the winter that the energy companies are forbidden by law to switch off the heating between Christmas and early March. The Midwest has roughly the same climate as Siberia; warm, hot summers, yes, but deadly winters, compounded by an Arctic wind chill blasting across Lake Michigan, hitting the city at gale force and burying it in snowdrifts. So it's primarily a spring-to-autumn tourist season. Chicago is basically two cities, or possibly three; its North Side and South Side, with a sprawling, emergent western sector with a growing latino influence. The South Side is traditionally poorer; largely a combination of tough old Irish and Italian neighbourhoods, and both middle-class African-American neighbourhoods and others that are viciously deprived African-American ghettos. It has fewer attractions for the tourist, although there are reasons for going there that I'll mention later. The best way to explore the city is on the "El", short for elevated train, which snakes around Chicago's buildings and over its rooftops, affording an unusual but excellent perspective of the city. In Chicago's Centre, known as Downtown, the red line El will take you to the shopper's paradise of the Magnificent Mile, and Marshall Field's, the city's flagship department store, now sadly a branch of Macy's. At the top of Mag Mile is the Water Tower, which is as far as the great Chicago fire got. Spare yourself shoe leather because the best way to see the stunning skyscrapers is by a Chicago Architecture Foundation cruise along the Chicago River. Make sure it's a warm day, so the cool breeze coming off Lake Michigan will provide joy rather than torment. An alternative perspective is offered from the observatory of the John Hancock Center, Chicago's fourth-biggest tower block in the city (the 108-storey Willis Tower, which until recently had been branded the Sears Tower, is the tallest in Chicago and the US). There is a restaurant and a bar there that is a tad more expensive than other places, but not the jaw-dropping rip-off you'd find in equivalent places in NYC or London. Generally, an old blue-collar ethos of fairness and value-for-money seems to underpin Chicago's attitude to commercial transactions. A must-see experience in Downtown is the brilliant Art Institute of Chicago, which sits on Michigan Avenue, on the edge of Grant Park, where President Obama made his victory speech. In the South Side's leafy academic enclave of Hyde Park, is the very impressive Museum of Science and Industry. In a city that isn't particularly child-friendly, kids can enjoy a full day in this labyrinth with plenty of activities to keep them occupied. Perhaps because of its harsh winters, Chicago often seems like one big festival from spring onwards, and it is a serious party town. Avoid Rush Street or Navy Pier and their saccharine, bland tourist charms, and head for the neighbourhoods. This is where you'll find the real spirit of the city. To the west there is Wicker Park, which contains places like the Bottom Lounge, where you can see established and emergent bands. Also, one of my favourite "dive" bars, Nick's Beer Garden, which stays open late. A rule of thumb for party heads is that most bars close at 2am, but the late establishments serve till 4am. A buzzing North Side neighbourhood is Lincoln Park, spiritual home of the famous "trixies", Chicago's toy-dog-walking, expensively sportswear-attired princesses, discerned by their trademark ponytails. The city has a plethora of fervently supported, yet often underachieving professional sports franchises. The Chicago Bulls, all-conquering in the Michael Jordan-era 1980s, share the United Center with the Blackhawks, the emergent force in North American ice hockey. The Bears football team play largely in the winter at Soldier Field, though, as you can imagine, this is an experience for only the seriously committed. It's baseball, though, that defines the cultural schism in the city - North Side versus South Side. The North Side-based Cubs are the establishment team, playing at Wrigley Field, the best old ballpark in the world. They have turned their home district, Wrigleyville, (named after the chewing gum dynasty) into one of the biggest party zones in the western world. Frat boys, office girls, suburbanites and tourists pour into this area full of bars and eateries, which often feels a bit like Cancun during Spring Break. Rival White Sox fans, and I'm one of them, will argue that the "loveable losers" (the Cubs have not won a World Series since 1906) have no substance, and for a real baseball experience, it's essential to take the El down to the South Side to US Cellular Field, a modern, high-tech ballpark, and watch the 2005 World Champions strut their stuff. It's one of the world's most fascinating sporting divides, and every visitor to the city should experience it. The big singles bar that is the Bleachers at Wrigley Field is best appreciated on a Thursday or Friday afternoon, when the office workers bunk off and romance - flirting often seem as much on the agenda as baseball and beer. Rather, the Sox come into their own on a warm evening where every home run is greeted with a fireworks extravaganza. If the baseball gets too much, you can repair to that bunker of wit and camaraderie that is "the Cell's" Bullpen Bar, one of my favourite spots in Chicago. Chicago boasts a couple of great racetracks at Arlington and Hawthorne, both excellent days out, and not to be missed is an hour-long drive down historic Route 66 to the industrial town of Joliet, Illinois, for the team demolition derby, a slice of America at its most down-to-earth. I've a soft spot for Chicago bars, as I met my wife in one of them. While the dive bars are great for atmosphere, there are also some sophisticated places; the plush Drake Hotel is one of my favourite spots. Such socialising though, should be done in conjunction with other nocturnal activities and the chief one in Chicago is music. It comes at you from everywhere; the ubiquitous neighbourhood festivals and the bars and clubs. If your tastes are traditional, go to Buddy Guy's Legends or Kingston Mines for blues, the Green Mill for jazz (you can also take an Al Capone tour at this old-timey joint that used to be one of the kingpin's hangouts) are essential venues. The best place to see a rock'n'roll band in Chicago is at Joe Shanahan's legendary Metro, opposite the Cubs' stadium. Chicago is also the home of comedy improv. The Second City, made famous by the Belushi clan, is the best known, though my personal favourite is the Improv Olympic on Clark Street. Local writers Bill Hillman (an ex-Golden Gloves boxing champion) and DonDe Grazia, (a former wrestler), run the Windy City Story Slam, an event which has achieved cult status as the happening cultural night out in town. Growing out of the city's literary and improv traditions, there is an amazing open-mic session where people just get up and rap out their tales. Brilliance and chaos meet at a literary event with a difference, where plenty testosterone, and often no short measures of oestrogen, are flying around. Theatreland in Downtown boasts the usual big musical standards, but more rewarding treasures are on offer at the local companies, which are usually based in the North Side. The Steppenwolf Theater Company, formed by, amongst others, the actors John Malkovich and Gary Sinise, is one to check out, as is the iconoclastic Blue Man Group. The restaurants range from high end to small neighbourhood joints (ignore the fast food chains) and are invariably of the highest quality and great value for money. Steaks and pizzas you expect to be good, but every block on Chicago's North Side seems to have a quality sushi or Asian fusion place. Also, and this came as a surprise to me, Chicago has the best Mexican restaurants in the US outside of California. Try Lazo's, a 24-hour joint where a mariachi band plays the night away, and if you've room for desert, Margie's Candies, across the road, will woo even those who don't have a sweet tooth. There are some great old American diners, the Melrose on Broadway being my personal favourite. If you're a bit more health-conscious, the Chicago Diner on Halstead is a vegan's paradise. All this eating and drinking is big fun, but a little challenging on the waistline. You might want to take a run along Lake Shore Drive or check out one of the city's plentiful gyms. The only real choice here is Quads on Broadway. In the heart of Cubs' territory, this South Side outpost is ran by White Sox fanatic Dave DeYoung. I go to gyms all over world, and Quads is simply the best one I've ever used. A very large and well laid out space on two floors, plus a third-floor boxing room, Quads somehow manages to feel intimate and attracts all sorts, from serious athletes and bodybuilders - local, national and international sports celebrities grace the walls with their testimonies - to the badly out-of-shape and everything in between. Crucially, it's excellent value, and you can pay daily, weekly or monthly, cutting down on the hassle and sense of rip-off travellers experience. There's stacks of equipment, so no matter how busy it is you can always get the weights, cardio machines or mat space you need, and at any time. A real institution, and one who's reputation goes way beyond the borders of the Windy City. Lake Michigan functions as an inland sea, and like all the coolest cities; Edinburgh, Sydney, Mumbai and Rio, Chicago has urban beaches. When it's stiflingly hot, it's always cooler by the Lake and looking out onto its still blue waters from the sand, you could be in San-Tropez. To get the best out of Chicago, pick up a copy of the free listings magazine, the Chicago Reader, which is the city's Village Voice. It's available from neighbourhood shops, supermarkets, and news-stands. Part of the heart and soul of Chicago, it provides often scathing criticism of Mayor Daley's political machine, which enjoys monolithic power in the city. I personally think that Mayor Richard M Daley is an excellent mayor who has done great things for Chicago, but every dynasty needs somebody to challenge it, and the plucky Reader generally does this better than the two newspapers, The Chicago Tribune and Chicago Sun-Times. Down the Mag Mile or in Lincoln Park, you can find just about as much metropolitan chic in this grand city as you can in New York and LA, and at a lot less cost. If you want something more besides, like warm, adventurous, can-do people, hearty food and darkly-lit joints where you can sit with strangers and put the world to rights, while the music plays on - in other words, a taste of the real urban America - then Chicago is the place for you.