THERE HAS BEEN a mistake. I shouldn't be here at all. I'm looking down the length of North Michigan Avenue, known as the Magnificent Mile, a compact concentration of department stores and designer houses, and I'm thinking this is all wasted on me.

For serious shoppers this is retail heaven: Chicago is fast becoming the first choice of Irish people planning shopping expeditions to the US. My mission is to shop for Ireland on this boulevard of bargain dreams, but I suspect I may not be up to the task.

I consider myself a bit of a metrosexual, reasonably familiar with the menswear section at Brown Thomas, but we're talking major-league shopping here.

"Why are they sending you?" asked Herself a few days previously. "They should send an expert - like me."

But, for better or worse, here I am in downtown Chicago, and the stores beckon to me with their promise of retail bliss and designer nirvana. Where do I start? Well, how about from the top?

The attraction of Chicago as an alternative shopping destination is apparent when you realise how easy it is to navigate the Magnificent Mile.

Although you can wear out your Manolos hoofing around Manhattan in search of the perfect pair of shoes, here you can practically glide up and down North Michigan Avenue, slipping in and out of the stores with cushion-soled ease.

Just in case you're suffering from New York withdrawals, the city's big department stores - Bloomingdale's, Macy's and Saks Fifth Avenue - all have branches here. There's even a Tiffany Co to soothe your inner Audrey Hepburn.

Most of the big design houses are here, too, including Hugo Boss, Prada, Burberry, Armani, Louis Vuitton, MaxMara, Zegna and - my favourite - Kenneth Cole. I picked up a nice wallet on sale. Talk about the last of the big spenders.

The Magnificent Mile is also dotted with shopping malls, from the 900 Shops at 900 Michigan Ave - billing itself as "above Magnificent" - to Westfield North Bridge at 520 North Michigan. Water Tower Place, across from Chicago's legendary Water Tower, is particularly impressive, with its eight-level atrium and fountains dancing alongside the escalators.

While the Magnificent Mile is dead handy - like O'Connell Street but without the pound shops - you're not going to find anything that you can't find in any other shopping capital. If you want something unique and individual, you'll have to get off Michigan and head for Chicago's boutique districts.

If you're only in town for a day or so, you may not have time to ferret out all the hot fashion houses. What you need is your own local guide, a style Sherpa who can help you negotiate the tricky terrain and hunt down those must-have items. So I signed up for a guided shopping tour of Chicago's neighbourhoods, led by stylist and shopping expert Danielle Lutz.

Imagine having your own Carrie Bradshaw to bring you to all the best boutiques and show you the best stuff on offer. Meeting up with Lutz and her clients at the appointed place, I feel as if I've just walked on to the set of Sex and the City. I'm the only bloke on the tour; this is tailored for serious shoppers, and serious shoppers tend to be female. If there's such a thing as a thoroughbred shopper, then Lutz is the real deal.

A former advertising executive, Lutz saw an opportunity to turn her vast knowledge of Chicago's boutiques and her expert eye for clothes into a profitable business. chicagoshopwalk.com has only been going for just over a year, but it's already striding ahead of the posse.

Today we're pounding the pavements of Bucktown, a pleasant, bohemian district just to the northwest of downtown Chicago. We meet at Café de Luca, on North Damen Avenue, where Lutz and the ladies discuss brands, styles, cuts and colours over a latte.

We hit the streets and head for the first boutique, and it's just like the TV show - high-heeled feet clacking purposefully along the sidewalk, designer handbags swinging nonchalantly, hair swishing back as the ladies stride out in search of some hot couture. And a big awkward Irishman shuffling behind in his sneakers and jeans.

We head into the first boutique on the trail, and the ladies make a beeline for the rails, expertly flicking through the clothes and chattering excitedly. I'm standing around self-consciously, trying not to look like a shoplifter, or a perv.

One bemused shop assistant asks suspiciously if she can help me. "Yes, please help me," I want to say. "I came on this shopping trip by accident. Can you arrange for my wife to be here instead of me?" Instead I murmur: "It's okay, I'm just the bodyguard."

When you sign up with Lutz you get not only the benefit of her expertise but also a discount at each boutique you visit. She'll even organise champagne and canapes - essential fuel for shoppers on the go. A two-hour tour costs $41 (€28), which could be a bargain if you want to maximise your shopping time and get straight to the fashion motherlode. But the real cost can be as much or as little as you like - few of Lutz's clients leave the boutiques empty-handed.

This summer Lutz has seen more European visitors signing up for the shopwalk tour.

I did manage to come away with one purchase - a pair of trendy FitFlops for the real shopaholic in my life. Next time around I'll just send Herself on the tour. Not even Carrie Bradshaw will be able to keep up.

• Kevin Courtney was a guest of Gochicago.com

How to get there, plus where to stay while you are on your US shopping trip

New York

• Three airlines fly to New York, Aer Lingus (www.aerlingus.com) and Delta (www.delta.com) to JFK, and Continental (www. continental.com) to Newark.

• Fares with Aer Lingus start at €410 in November, including taxes and surcharges. Continental and Delta have fares of €522, including taxes and surcharges. All fares are based on midweek departures.

• Holiday Inn Midtown (440 West, 57th Street, 00-1-212- 5818100, www.icohotelsgroup. com) is a good location for getting around the city. Lastminute.com has three nights and flights from €866 per person sharing.

• The Pennsylvania (401 Seventh Avenue, 00-1-212- 7365000, www.hotelpenn. com) may not be the fanciest hotel in New York, but you can't beat the location for hauling the shopping back from Macy's. Check 1800hotels.ie for four nights' accommodation from €324 per person sharing. It also has the Marriott Financial Center (85 West Street at Albany, 001-212-3854900, www.marriott.com), which is ideal for Century 21 and the Wall Street area, from €469 per person sharing.

• Uptown, our favourite hotel, Fitzpatrick's Hotel Grand Central (141 East 44th Street, 1850-644464, www. fitzpatrickshotels.com), is throwing in tickets for the Empire State Building with four nights for €569pps.

• If you want to get away from the mad buzz, the Hotel Beacon, on the Upper West Side (2130 Broadway at 75th Street, 00-1-212-7871100, www.beaconhotel.com), is a great option. Only three blocks from an express subway and handy for the theatre district, Lincoln Center and Central Park, it is in a friendly neighbourhood with trendy diners and restaurants. Its two-room suites are ideal for families.

• American Holidays (www. americanholidays.ie) might have the ultimate in a girls' trip to New York: it will throw in a Sex and the Citytour with your three-night package staying at the Edison Hotel (228 West 47th Street, 00-1-212- 8405000, www.edisonhotel nyc.com), from €668 per girl sharing.

Boston

• Return flights with Aer Lingus from €466, including taxes and surcharges.

• The January sales begin on December 26th. You could be there for six nights, staying at the Hilton from €889pps with www.touramerica.ie.

• Spoil yourself at the Sheraton Braintree (37 Forbes Road, Braintree, 00-1-781- 8480600, www.starwood.com) for €716pps with www.lastminute.com.

• Shopping quads (rooms for four people sharing) at the Nine Zero Hotel, near Quincy Market (90 Tremont Street, 00-1-617-7725800, www.nine zero.com, for €218pps with www.1800hotels.ie.

• For shopping on Newbury Street, you cannot beat Jurys Boston Hotel (350 Stuart Street, Back Bay, 00-1-617- 2667200, www.jurysdoyle. com/ boston) for calm - and it's within staggering distance when you desperately need to drop off those shopping bags.

Chicago

• Fares with Aer Lingus start at €515, including taxes and charges. American Airlines (www.aa.com) also flies from Dublin, with fares from €529, including taxes and charges.

• Lastminute.com has the four-star Swissôtel (323 East Wacker Drive, 00-1-312- 5650565, www.swissotel chicago.com) from €722pps.

• 1800hotels.ie has a four-night deal at Essex House (800 South Michigan Avenue, 00-1-312-9392800, www.essex inn.com), from €191pps.

• On the Magnificent Mile, 1800hotels.ie has four nights at the four-star Sheraton (301 East North Water Street, 00-1-312-4641000, www. sheratonchicago.com) from €299pps.

Philadelphia

• The City of Brotherly Love is a great place to shop, especially as it imposes no taxes on clothing. US Airways (www. usairways.com) flies every day from Dublin, with fares from €534, including taxes and charges.

• The Marriott (1201 Market Street, 00-1-215-6252900, www.marriott.com) is offering three nights from €586 through www.lastminute.com.

• Great value for friends sharing, quad rooms for four nights cost from €69pps at the Holiday Inn Historic (400 Arch Street, 00-1-215- 9238660, www.ichotelsgroup. com) with www.1800hotels.ie.

• The downtown Best Western (501 North 22nd Street, www.bestwestern pa.com/philadelphia-hotels) has a three-night package from www.americanholidays.ie, from €563pps.

San Francisco

• The west coast may seem a long way to go for a shopping break, but San Francisco is a lovely city.

• Fares with Aer Lingus start at €634, including taxes and charges.

• Touramerica.ie is offering five nights in San Francisco, staying at the Holiday Inn, from €765pps.

Orlando

• Great shopping in the sunshine state. Touramerica.ie has seven nights at the Quality Inn, with US Airways flights, from €779pps, for travel in October.

Joan Scales