The Zen one

PARK HYATT

To be precise, Zen and the art of having your whims met before you’ve whimmed them. Rooms are crisp and modern but ooze tranquil calm. You might be tempted to sit crosslegged on the floor, but the designer furniture or windowside bench will soon seduce you. Modern elements include free WiFi, whizzy entertainment systems (including a hook-up for your iPod), electric blinds and a plethora of switches and dimmers to play with. And the beds are enormous. Get a room on the eastern side for views that extend over the Water Tower, one of the few buildings to survive the great Chicago fire of 1871, and beyond to glimpses of glistening Lake Michigan. In a city that can feel a bit old-fashioned, this hotel stands out for its modern luxury. It even had a scent expert come in and design nice smells for the rooms.

00 1 312 335 1234, parkchicago.hyatt.com; doubles from £217

The classic one

THE DRAKE

A grandiose foyer, a cello’s liquid tones drifting down the stairs, galactic chandeliers, an angel on the ceiling, and oodles of brass and gold. This is one of the oldest hotels in Chicago, established in the 1920s, and while it’s changed hands a zillion times, white-glove service has been a constant. All rooms have views of a Lake Michigan beach or the glitzy Magnificent Mile designer drag. It’s an excellent location. Solid, timeless charm and plump comforts adorn the rooms, and they have attracted the likes of the Queen, Princess Diana, Margaret Thatcher and a string of presidents. Some of the other guests are the best attraction, from poodle-toting New York darlings to this week’s pop tarts. Scenes from Risky Business and My Best Friend’s Wedding were shot here. A Chicago institution.

00 1 312 787 2200, www.thedrakehotel.com; doubles from £79

The bargain one

THE SENECA

Being in this hotel is like watching a movie on VHS – it’s all a bit dated, and some of the finer details have gone missing. But, amazingly, it’s bargain-bin cheap and bang in the middle of Chicago’s ritzy bits. The strutting darlings perusing nearby boutiques would be mortified to know that such old-fashioned value exists on their patch. Cheapskates, on the other hand, will rejoice in the fact that it hasn’t been renovated in approximately for ever and yet still passes the “Would you let your mum stay here?” test. Some rooms are a bit like small apartments, with kitchenettes, and come complete with a certain homely charm. All in all, it’s as comfortable and as fashionable as your favourite hand-me-down cardigan, and you won’t have to rummage around in dark suburbs to find it.

00 1 312 787 8900, www.senecahotel.com; doubles from £58

The hip one

THE JAMES

Not quite two years old, The James is still basking in the white-hot affection of Chicago’s hipster crowd. There are bowls of water and dog biscuits by the door for fashion-accessory pooches (or local mongrels that get in quick while the smartly dressed doorman isn’t watching), not to mention gourmet bones and cat cuisine on the menu. Tuna tartare, anyone? Beautiful people mill around in reception, looking at each other looking wonderful. If you’re lucky enough to be able to get a room, it will be delirious with crisp and artsy design-mag adornments and built-in furniture. And if you can’t find the minibar among all that, you can pop into the adjacent Jbar for a cocktail. Hotel guests get VIP treatment – just the place to kick back with rock stars and celebrities and the dogs that follow them home.

00 1 312 337 1000, www.jameshotels.com; doubles from £150

The homely one

THE TALBOTT

The owners of this anglophile triumph are Chicago socialites who pop over to the Old Country from time to time and bring back a passion for country-manor hospitality. There are working fireplaces in the foyer, along with chesterfield-style sofas, fox-hunt pictures and a veritable orchestra of brass bugles scattered about. Rooms are also upper-crust comfy, with large beds, plump furnishings, brass fittings and solid wooden furniture. While the look is ye olde tweedy, everything else is very modern. Service is have-a-good-day American; mod cons include free WiFi throughout, little glowing “privacy” signs outside the doors, operated from inside the rooms, and doorbells for those who wish to ignore them. If only they’d add a nice hotel hunting dog, everything would be simply spiffing.

00 1 312 944 4970, www.thetalbott.com; doubles from £80

Travel brief

Virgin Atlantic (0870 380 2007, www.virgin-atlantic. com), British Airways (0870 850 9850, www.ba.com), American Airlines (020 7365 0777, www.american airlines.co.uk) and United Airlines (0845 844 4777, www.unitedairlines.co.uk) all fly from Heathrow to Chicago O’Hare airport; BMI (0870 607 0555, www.flybmi.com) and American also fly nonstop from Manchester. Prices start at about £400. O’Hare airport is 17 miles from the city centre. The quickest and most reliable way into town is on the Blue Line “L” train, which takes 45 minutes and costs 90p, one-way.

Andrew Quested stayed as a guest of the Park Hyatt

Times recommends

• Travel advice: what to do if your flight is disrupted
• Top 10 unmissable events in 2010
• Seven spa breaks for January