If you’ve got a substantial budget, this is where you should be staying. The service is impeccable and they have a team of administrative assistants in the business centre that will take dictation, research things for you, organise your diary – in fact, anything you might need while in the city can be sorted out from this hotel. You also get to use their amazing spa facilities, which cover the top two floors of the building.
There’s an athletic club at the Hilton at O’Hare airport which offers day membership for about $10, and has a pool, sauna and gym – worth bearing in mind if you arrive at the airport to find a long delay on your flight.
Hilton at O’Hare airport
If you’ve got something to celebrate and feel like splashing out, the 23-course tasting menu at Alinea in the Lincoln Park area is a must. It’s an eye-popping $195 at first glance, but with the exchange rate as it is, it does represent excellent value. Everything is exquisitely presented and tastes wonderful.
Spend about an hour getting a real sense of Chicago's layout and history by cruising the rivers on an architectural boat ride. Make sure it is an authorised and well-reviewed outfit.
While the airport’s accessibility is stellar, its usability is anything but. It has 168 gates, a sprawling mass of barely intelligible corridors, abysmal shopping, hugely long security queues and – worst of all – almost inevitable delays. My advice? Make absolutely sure you buy a fully flexible, premium class ticket – this will enable you to use the security fast track, the premium lounges and, even better, change your flight at short notice. Or avoid O’Hare altogether. If you’re flying within the US, try to fly into Midway or Rockford – they’re much smaller and significantly less hasslesome.
The closest Chicago comes to boutique chic is the W Lakeshore hotel and The James. The acceptable face of the Sheraton Group, the uber-hip W chain has a strong following among businessmen looking for something a little wacky after a hard day’s work with fellow suits. As you enter this particular W outpost, you’ll be greeted by blaring house music, hot staff and a not-so-subtle barrage of fluorescent lighting. It might sound a touch ghastly but it’s actually a magnificent hotel centrepiece and, cleverly, the owners have complemented the insolent noise downstairs with splendid silence upstairs.
The rooms are quiet, rich in minimalist, understated luxury with fabulous views of Chicago’s ultimate attraction – Lake Michigan. The Extreme Wow Suite, all 1,100 square feet of it, is a great way of blowing your budget.
There are plenty of taxis outside the airports and, for those who were brought up watching 'To The Manor Born', you can book a limo to whisk you to your 5-star hotel suite in comfort (as in most US cities, Carey are the best provider). But public transport is probably your best ticket. Chicago is in fact, very unusually for the US, thoroughly served by public networks of buses and trains. The El Al, a rather spiffing elevated train, is the quickest and cheapest mode of transportation between O’Hare, Midway and The Loop.
If you’re after old-world charm, I can strongly recommend The Peninsula or the Four Seasons. The Peninsula is located in the middle of Chicago’s magnificent mile of department stores and designer boutiques, has a fabulously grand lobby and is home to Shanghai Terrace – arguably Chicago’s finest Chinese restaurant. The lobby lounge is lit by twenty-foot-high windows, and the bar, in contrast, is intimate and low-lit, with a roaring fireplace and a surprisingly hip crowd. Despite its excessively grand décor, I’ve always found it very difficult to leave the Four Seasons – the CEO hotel of choice. The service is friendly, super-competent and never intrusive; the views spectacular – of the Michigans (Avenue and Lake); and the pampering genuinely top-notch.
The New American food at Seasons is delicious and you can easily lose a week at the extraordinary spa and pool. Every bit as impressive as its New York sibling, the Chicago Seasons happens to be cheaper, too.
The Peninsula Chicago 108 East Superior Street (at North Michigan Avenue), Chicago, Illinois 60611, USA Tel: (1-312) 337 2888Fax: (1-312) 751 2888 chicago.peninsula.com
Four Seasons120 East Delaware Place, Chicago, Illinois, U.S.A. 60611-1428 Tel: 1 (312) 280-8800 Fax: 1 (312) 280-1748
Charlie Trotter’s on West Armitage is very expensive but also worth it: the epitome of New American gastronomy, punters are consistently dazzled by the freshness of the ingredients, the innovation of the daily changing menu, the exceptional wine cellar and the courteous and knowledgeable staff. It’s a touch over-formal but, after a few bottles, you’ll forget the stuffiness.
A tip: for the ultimate, sublime experience, get a reservation at the kitchen table. Also formal but utterly magical is TRU in Streeterville. A rather unique combination of gallery and eatery, this hip establishment houses two of Chicago’s most eminent chefs (Rick Tramanto and Gale Gand), sommelier Scott Tyree’s 1,400-bottle wine selection and an original Andy Warhol. From the moment you enter through the deliciously decadent black drapes, you’ll be stunned. Try the caviar, kobe beef and truffle-garnished scallops for a lasting memory. And don’t forget to wear a (louche) jacket.
Charlie Trotter's, 816 West Armitage Chicago, Illinois 60614 Tel: 773 248-6228
If you’re looking for food with a view, try The Signature Room at the John Hancock Centre. With better views than the building’s observation deck, this is Chicago’s brunch centre. The prices are reasonable and you’re guaranteed to wow your colleagues/clients. The service can be a little variable – it took the waitress 15 minutes to find me a fork – but the weekend live jazz more than makes up for the occasional shoddiness.
The Signature Room at the 95th® 875 N. Michigan Ave. Chicago, IL 60611 Tel: 312.787.9596
For something completely different, try X/O in Boys Town. This ultra cool spot dishes a delightful variety of creative eclectic small plates – including tapas with a twist – and offers some of the city’s best cocktails. The champagne concoctions and martinis are as spectacular as the atmosphere – fuelled by a DJ with a Hoxton haircut at weekends. If you can, try to sit on the patio.
3441 N Halsted Street Chicago, IL 60613 Tel:(773) 348-9696
Fancy a boogie? Sound Bar and Enclave are your passes to the best late-night hedonism Chicago has to offer. The former has two levels and is invariably packed: downstairs plays hip-hop music and upstairs grooves to an unrelenting house beat. You can engineer your very own oasis of calm, though, by booking a table in the VIP room. The drinks are phenomenally cheap, you get waitress service and the chance to retreat if the music becomes too much or the people too raucous. Not the best club in the world, but a good laugh nonetheless. Altogether better is Enclave. This upscale location has undergone a full year of renovation: new floors, new (clean) bathrooms, new furnishings, impeccably styled bar areas, etc. And it’s been worth it. This is now the premier dance spot in Illinois, with beautiful people to match. Get a table in the circular, curtain-swathed VIP area and forget all about work.
If you’re looking for a post-dinner drink or two, the J Bar at The James is a good place to start. In harmony with the rest of the hotel, it’s sleek, sophisticated and very cool. The barmen fashion martinis with olive lollipops (so you can look like Kojak for the night) and the waiters provide appetizers from David Burke’s in-house restaurant. If you get there early enough, you might also get a seat on the attractive low-slung banquettes.
James Hotel55 East Ontario, Chicago, Illinois, 60611Website: jameshotels.com/chicago
Sears Tower remains the tallest building in the Western hemisphere and, as such, is worth a gander. Soldier Field, home of the Chicago Bears football team, is a local Mecca and if you can, catch a game while you’re there. Or, in the summer, Lake Michigan has to be destination numero uno: lie on the man made beach, play volleyball, swim or, if you’re into touristy attractions, hit Navy Pier and its 50 acres of parks, promenades, gardens, shops, eateries and more.
If you're in the mood for a bit of culture, Chicago’s Museum of Contemporary Art (MCA) is worth a visit. One of the largest facilities devoted to modern art in the US, the MCA offers exhibitions of (they claim) “the most thought-provoking art created since 1945”. The MCA documents contemporary visual culture through painting, sculpture, photography, video and film, and performance. It’s easy to get to, has a passable restaurant, a fab 300-seat theatre, and a terraced sculpture garden with a great view of Lake Michigan.
220 East Chicago Avenue, Chicago, IL 60611 Tel: 312.280.2660Website: mcachicago.org
The Magnificent Mile on Michigan Avenue is a remarkable homage to consumerism. With four enormous malls and a host of favourite designers – from Gucci to Prada and Levi’s to Ralph Lauren – it’s the ultimate “one-stop-shop”: you can find the perfect birthday, anniversary or Christmas presents here. And there’s shopping outside the Mile, too – in the shape of some fabulous little specialist boutiques. Try Sam & Willy’s for everything a dog could want; or the H.I.M men’s clothing boutique; or Unique So Chique Tea & Chocolat for a glittering array of bath and body products, cards and stationery.
BMI fly direct to Chicago from Manchester. Don't forget regional airports when flying abroad - when you take into account heavier congestion around the London airports, it may prove to be quicker to fly from the regions.
The Art Institute of Chicago is well worth a visit. The arts are not usually my thing, but the collection here is very varied and packed with works from numerous well-known artists. As a relative novice when it comes to art appreciation, the audioguide proved a real boon for getting the most out of the visit. The building is light and airy, and situated in a wonderful spot on the shores of Lake Michigan.
Art Institute of Chicago111 South Michigan AvenueChicago+1 (312) 443-3600www.artic.eduNearest metro stations: Van Buren/Millennium
Make sure you catch a morning flight to Chicago - you'll arrive in time to catch an afternoon architecture tour of the city, by river boat. Chicago's the home of the skyscraper, and you get some awesome views of some of the world's first, and finest, tall buildings from the river. From Trump Tower to the Wrigley dynasty's HQ, you'll feel like you know the city a lot better at the end of the tour. The guides are great - typically friendly mid-Westerners keen to share their enthusiasm for one of the world's great cities.
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