Ask an Angeleno and ask a New Yorker and you’ll get two totally different answers. That’s why we picked one city that knows about cold: Chicago. Then we came up with a scale – brisk, biting and bleak – and checked in with our friends at the weather app Swackett to give precise meanings to these not-so-scientific terms (more on that in the 'How it works' tab). So you'll get the best deal when the forecast in Chicago hits bleak – whether you live in Seattle or St Louis.

Check out our weekly brisk, biting, bleak pricing forecast. We’ll update the rates – based on Chicago’s weather – every Monday at 10am EST. Here’s hoping Chicago freezes over.

• Flight + hotel bookings are non-cancellable, non-refundable and non-changeable
• All travel bookings based on availability and subject to black-out dates
• Flight + hotel promotion valid only for residents of the United States
• Book by March 31 2015, stay by May 22 2015
• Flight component must be operated by American Airlines, not an affiliate airline or a codeshare partner
• Flight + hotel pricing based on Chicago forecasts provided by Swackett and published on this page every Monday morning EST through March 31 2015
• Flight + hotel pricing is applicable on the day of booking, not on the day of the enquiry or travel i.e. book on Bleak day for Bleak pricing
• Flight + hotel bookings can only be submitted via enquiry form and must be confirmed by a Smith24 agent
• Costs for checked baggage are not included in the flight + hotel quotes provided
• Name changes to individual flight bookings are not permitted after ticketing
• Aadvantage mileage accrual is permitted on select fares -- Aadvantage rules and restrictions apply
• Upgrades will be allowed according to the terms of the American Airlines Aadvantage program

Above freezing is almost balmy by Chicago standards, but it’s still not bikini weather. When the mercury hovers above 32º, you can flee New York (for example) on a Saturday morning, spend two days splashing at Metropolitan by Como, Miami Beach and still make it to work on Monday for just $1,510 (regularly $1,636) for two, including flights. 

Is that ice on the Bean? In these conditions not even a 110-ton sculpture can evade the chill. You, on the other hand, can skip town. When Chicago freezes, flights from NYC, plus a two-night stay at Metropolitan by Como, Miami Beach will run just $1,458 (compared to $1,636) for two. 

Bleak has never been so upbeat. That’s because negative temps make for our most aggressive, pack-your-bags-now rates. Hightail it from NYC to Miami for the whole weekend and luxuriate at Metropolitan by Como, Miami Beach for only $1,402 (compared to $1,636) for two, including flights. The money you save could make a nice addition to your spa fund.  

Trailblazing travellers looking for the latest should head to Thompson Miami Beach. This newbie, which just opened in November, has mid-century-meets-art-deco decor and a Mid-Beach address. Stay in an ocean-view room with a private balcony and sample the fare at Seagrape, the hotel’s Florida-centric brasserie from James Beard-awarded chef Michelle Bernstein. Then, report back to all your friends and fellow trendsetters.     

Relax. That’s the idea, right? This ocean-side spa sanctuary is just the place to do it. Unwind with signature massages, hydrotherapy and free daily yoga. But just because these digs are downward dog-friendly doesn’t mean you have to stick to coconut water. The hotel’s gin bar, which has over 30 artisanal varieties, provides the right amount of revelry. 

There’s a reason supermodels, actors and fashion designers flock to Soho Beach House. The place oozes style. Rooms are outfitted in worn leather armchairs, antique wardrobes and mirrored bar cabinets. Then there’s the members-only Club Bar (hotel guests get access, don’t worry), which takes its design cues from old-school Havana. And did we mention there’s a photo booth on the grounds? C’mon, you’re never too cool for a photo booth.     

Explore ancient Mayan ruins, stroll hand-in-hand through pristinely-preserved colonial plazas or contemplate the sparkling ocean from your beachfront hammock. Mexico – spanning the tranquilo Riviera Maya and Tulum to the artist outpost of San Miguel de Allende and a surf and spa hideaway in Los Cabos – entices sun-seekers of every sort. 

The exotic locales of Belize, Guatemala, Panama and Costa Rica may seem a tad off-the-well-trodden path – but who needs a crowd, anyway? With kitted-out treehouses, chic eco-suites in the jungle and private beachy bungalows, there's no skimping on secluded hideaways where you can relax, be pampered and soak up the sol in Central America. 

Lush rainforests, coral-fringed isles and sapphire sea views for miles, it's no wonder the jet-set flock like rare birds to the charasmatic Caribbean. A colourful swirl of influences and cultures, you can trot out your best French in St Barts and St Martin, practice your Spanish in the Dominican Republic or pick up on the patois in Jamaica, mon – all while perfecting that winter tan. 

Don your most glamourous shades and head West, sun-worshippers to the Pacific Coasts of California and Hawaii. The Golden State is a diverse playground with the arid Palm Spring desert to swimming pools and movie stars of Los Angeles and waveriders of San Diego and Santa Barbara. Or, say Aloha to surf, sand and yes, unlimited sunshine, in Honolulu.