Romantic breaks: Chicago

Rebecca Twomey

If you want sparkle sunbathe in LA, if it's style you're after get shopping in New York but for soul head straight to Chicago. Away from the glitz and glamour of the country's coastlines lies middle-America's Chicago, the city that channels an authentic gorgeousness combined with an attitude that doesn't need to try to be cool.

True to the American dream, Chicago strives for success, pouring all its profits back into the city, supporting young entrepreneurs and encouraging local business that results in countless shops, restaurants and clubs owned by trend-savvy 20-somethings and not personality-void chains. This only adds to the city's allure - small vintage shops are a ten-minute taxi ride from huge department stores and the people put passion into their jobs.

Don't expect the locals to be fazed by that fact you're British, but do expect them to start talking to you in the street and help you with your bags. Surprising stuff, considering it's the third largest city in the states and one you'll be itching to explore...

Handbag's compass to the city:

What to do
Before you do anything else (including buying a guidebook) book a Chicago Greeter tour. This incredible insight to the city is entirely free and uniquely tailored to what you want to discover. Expert volunteers from the tourist office show you Chicago themed to your interests be it fashion or food, architecture or adventure. Not only will you get to grips with the workings of the city but you'll also get a free one-day travel pass. Handbag naturally went for the fashion tour and met with young designers supported by and working in the offices of Macy's then headed round beautiful boutiques off the beaten path before having lunch in a typical American cafe.

For the rest of your stay continue to indulge in being a tourist and trap yourself in the four main districts that each spill over with personality.

The Loop
Downtown, also know as the Loop, has a showering of department stores and scattering of skyscrapers that are unassuming even though the Willis tower, formerly and more famously known as Sears Tower, is the tallest building in the states. Test your vertigo here and be transported to the top of the building where, after a brief video on the history of the city and its construction, you'll be standing on a Perspex balcony, named the sky deck where you can see what it looks like to peer down 1,450 feet standing on a plastic box.

Armed with your credit card make sure you mark out some serious time to wonder Michigan Avenue. Trust us, it isn't known as the Magnificent Mile for nothing. With American classics, Bloomingdales, Macy's and the barganista's fave, Forever XXI framing the street, you'll max out your card in minutes. Put your flats on and ditch your man if he's not the shopping sort and make your way to Oak Street that's home to designer shops including Jimmy Choo and Chanel.

Hold hands as you take a stroll around Millennium Park and hit the Art Institute of Chicago, here hangs paintings from the 19^th century alongside modern installations.

Lincoln Park
If you're a sunny season visitor, Lincoln Park Zoo is a predominately outdoor attraction and is free, but animal activists may want to stay away, unlike British zoos, you can get a little too close to the inhabitants and the enclosures can seem a little small.

For a sweet treat pop into Vosges Chocolat shop who will provide you with chocolate and wine pairings and enough sugary stuff to boost up you energy to do a few laps of Lincoln Park that runs parallel to Lake Michigan and boasts pretty views.

And if you failed to find a bag on Michigan Avenue, unlikely, but if you need an excuse to splurge on another 1154 Lill Studio is a special shop that lets you design your own bag - chose your preferred style - tote, clutch, shopper etc then customize it as you choose.

Wicker Park
The arts crowd resides in the cultured cave of streets that is Wicker Park, littered with vintage shops, cool brands, tiny art galleries with pop art and music shops - hardly surprising for the city that started house music. Once you've scoured the rails of the countless little shops head to Akira, like an enormous dressing up box this hugely successful store (started by a group of Chicago friends) sells everything from the one-off pretty pieces to wardrobe basics and in a range of prices - bargain and bank-busting.

Southport
For yummy mummy-ville head to Southport - it's picture-book America with wide streets that seem to go on for eternity with no traffic and lots of small stores. Worth stopping in is Candyality, a retro sweet shop stocking every sweet imaginable in the most random of combinations - chocolate-covered gummy bears, the inside of butterfingers and Friends fave, tootsie rolls. The clothes shops are all boutiques and can be pricey but good for window shopping.

Where to eat
Along with the rest of the states, portion sizes in Chicago are button-popping worthy, and nowhere is this more true than at Giordano's pizzeria. Deep dish pizza was born in the city so is loved by the locals which means you'll usually have to wait an hour for a table, but if you want to sample something typically Chicago then it's worth it. The stuffed pizza pies on offer are gigantic - trust us you'll only manage one slice of melted cheese magic but you'll get a doggy bag to take home.

No trip would be complete without a lunch at authentic American 50s diner Ed Debevic's. Don your prom dress and pumps, get a booth and live out your Grease fantasy by ordering burger and fries served in a basket to the backdrop of old school tunes. The staff take the unusual stance of insulting their customers, dancing on the tables and providing entertainment while you eat.

If you're after dinner for two, just by Lake Michigan is Sixteen, housed in the Trump hotel, the restaurant offers fine dining with delicious finesse. Go for the tasting menu of eight different courses that are all equally decadent and drool-worthy.

Downtown you'll find Café des Architects a less formal restaurant that shuns typically American food in favour of more elegant European dishes in sleek surroundings.

Where to drink
Chicago locals are so passionate about their city they'll do pretty much anything to help you discover its hidden treasures, which is exactly how we found the secret watering hole that is Violet Hour. While on the hunt for a chic bar, people pointed us to a ‘hidden door', once in you'll fight your way through heavy drapes and enter into a candle-lit bar. The chairs face each other so you can only see the person you're with and have ridiculously high backs, perfect for a romantic evening for two. It's anti-trends so your mobile is banned and you'll only find the bar's signature cocktails on the menu.

If it's a stunning setting and dramatic views you want with your drinks then take the lift up to the 96th floor of the John Hancock building where the Signature Room resides. As you drink in views of the city you can enjoy a tipple or two, but make sure you go mid week in the early afternoon as on the weekends it can get ridiculously busy.

Where to stay
Chicago has no shortage of cool and chic hotels, it's most elaborate is Trump hotel where you can lavish luxury on yourself and your man even if it's for one night. The incredible attention you receive from the staff plus a superb room with floor-to-ceiling windows that frame the city's sights immaculately are well worth spending out for. The best bit by far is the bath that's a mini-swimming pool with a television built into the mirror. Trust us, you'll never want to leave your room. For a romantic retreat the newly built Elysian hotel has chic trimmings carefully carved out and is seconds away from the shops of the Loop. For a more modest hotel, stay at the Fairmont it's centrally located and has two great restaurants plus a gorgeous spa that you mustn't miss out on visiting.

What to pack
It's not known as the windy city for nothing, in the winter months temperatures can shoot down as low as -13 degrees, and the icy wind can burn around your lips which means standing still isn't an option. Comfy flat boots are a must for the day time but bring your heels for the evenings as you hop from cab to club. All indoor areas are toasty warm so every time you enter a building you'll be thawed out quickly, which is why packing loads of layers is a must.

Useful information
Most people in Chicago drive, so asking about public transport or directions should be left to the hotel concierge, the El train stops can be a bit far away from each other but armed with a map you won't miss much. Taxis can get pricey over a few days stay so get a $20 week's CTA pass that'll get you on buses and trains around the centre. And always carry a wad of $1 notes for tipping, as with the rest of the USA, Chicago is mad for it.