Chicago
Chicago

istock / Agnieszka Gaul
Chicago is one of those enigmatic cities that’s home to myriad distinct cultures and communities, but somehow maintains its own unmistakable identity. It’s more than the windy city grit or the unique challenge of being a Cubs fan. With its galleries, theatres and jazz lounges, Chicagoland is the beating heart of culture between the coasts, but you’ll still find touches of Midwestern modesty. As long as you don’t start talking sports, that is.
Hotels

The Wit
The Blackstone
636 S. Michigan Ave., Chicago, 800-468-3571, blackstonerenaissance.comPast and present are equal partners in casual sophistication at this recently restored historic hotel. Rich wood panelling, marble details and grand crystal lighting evoke its 1910 provenance, while pop-inspired palettes, mid-century furnishings and local contemporary art quietly modernize. Absorb superior views of Lake Michigan and neighbouring Grant Park from a plush leather lounger in a generously spacious room.
Hotel Burnham
1 W. Washington St., Chicago, 877-294-9712, burnhamhotel.comIf you’ve ever fantasized about going back in time – to, say, the ornate, metal-filigreed 1890s – without giving up modern luxuries like in-room spa service, American café classics on call and easy access to some of the world’s best retail, consider checking into Hotel Burnham (situated in one of Chicago’s oldest and most beautifully preserved skyscrapers, the Reliance Building).
The Wit
201 N. State St., Chicago, 312-467-0200, thewithotel.comDowntown Chicago’s newest statement piece looks, feels and smells (with its signature building-wide diffused aroma) like “The Future of Hotels.” It might seem as though it’s trying too hard – the neon green zigzagged façade, the HD movie theatre, the multimedia library, the trendy rooftop club (named, seemingly with a straight face, Roof) – but it works.
The Dana Hotel and Spa
660 N. State St., Chicago, 888-301-3262, danahotelandspa.comThe Dana blends laid-back, earthy style with luxurious flourishes. Its serene rooms –featuring floor-to-ceiling vistas – feel like mini-spas, with plank wood flooring and sea-coloured walk-in rain showers. The Zen vibes extend to the indoor/outdoor Vertigo Sky Lounge and the in-house restaurant Aja, where sharing custom-spiced Asian dishes is encouraged.
The James
55 E. Ontario St., Chicago, 877-526-3755, jameshotels.comThis modern boutique spot is stylish without sacrificing comfort – your stay is like being invited to house-sit for your most fashionable friend. Fresh flowers, art and design books, in-room café tables with cushy seating and bathrooms stocked with Kiehl’s products are just a few of the better-than-home homey touches. Reserve a complimentary bike for a cruise around the Loop.
The Elysian
11 E. Walton St., Chicago, 800-500-8511, elysianhotels.comThis new hyper-luxe boutique property in the posh, lakefront Gold Coast is out to set a new bar for opulence. Think polished silver, white marble tubs, fine Italian linens and in-room fireplaces. Think two in-house restaurants – Balsan and Ria – that were generating excited chatter among critics months before they opened and luxury retail on the premises (Marc Jacobs has signed a lease). Think about booking far in advance.
Amalfi Hotel Chicago
20 W. Kinzie St., Chicago, 877-262-5341, amalfihotelchicago.comAn attractive and modern River North property, the Amalfi stands out with a super-attentive staff (they call their concierges “experience designers”) and boutique touches like coffee and sweets on every floor.
Sofitel Chicago Water Tower
20 E. Chestnut St., Chicago, 800-763-4835, sofitel.comA dazzling 415-room glass tower designed by Jean-Paul Viguier, the Sofitel Chicago Water Tower offers a modern French retreat within steps of the Magnificent Mile.
Food & Drink

Jeff Kauck
Nightwood
2119 S. Halsted St., Chicago, 312-526-3385, nightwoodrestaurant.comThe proprietors of the beloved (and still thriving) Lula Cafe recently opened their next cult favourite in Pilsen, the city’s of-the-moment neighbourhood. The menu changes daily – handwritten selections depend on what’s fresh and locally available – but you can count on a perfect wood-grilled cheeseburger or spit-roasted chicken any day of the week.
Terzo Piano
159 E. Monroe St., Chicago, 312-443-8650, terzopianochicago.comTerzo Piano and its home, the stunning new Modern Wing of the Art Institute, have an important thing in common: They both offer accessible encounters with the transcendental. Terzo’s artistry is in its fine-dining-calibre pasta dishes, prepared at a reasonable price by Beard Award-winning chef Tony Mantuano.
The Publican
837 W. Fulton Market, Chicago, 312-733-9555,, thepublicanrestaurant.comThe Publican is Chicago’s much-lauded contribution to the artisanal meat craze. If impeccably prepared pork rinds, charcuterie plates or sweetbreads aren’t your thing, the painstakingly curated craft beer list alone is a reason to visit.
Xoco
449 N. Clark St.,, 312-334-3688, rickbayless.comThe latest venture of Chicago’s own Top Chef Masters winner, Rick Bayless, is an upscale take on Mexican street food. Opt for a breakfast of all-butter conchas or egg tortas to beat the crowds or stop for a mid-afternoon snack of churros and house-made Mexican hot chocolate. Bayless makes regular appearances (and poses for pictures).
David Burke’s Primehouse
616 N. Rush St., Chicago, 312-660-6000, jameshotels.comA stay in the stockyard city is never complete without a steak. David Burke shakes things up with prime New York cuts from pasture-raised beef, aged in-house. Seafood options like pan-roasted red snapper and surf-and-turf dumplings also stand out. For those with big appetites, the signature “Slice of Prime” s’mores cake will guarantee a happy food coma.
Avenues
108 E. Superior St., Chicago, 312-573-6695, peninsula.comWhile this may be a white-tablecloth establishment known for its faultless service and location in one of downtown’s most exceptional hotels (The Peninsula), it still has a sense of fun: Bar seats in the “exhibition kitchen” provide front-row views of the preparation of four-star eight- and 15-course contemporary American menus.
Blackbird
619 W. Randolph St., Chicago, 312-715-0708, blackbirdrestaurant.comYou might as well go for broke with chef Paul Kahan’s divine, hit-every-note tasting menu: Foie gras torchon with quince, poached lobster, slow-roasted Carolina squab, prime beef short rib with sesame gnocchi and chocolate pavé with pomegranate are just some of the highlights from its 10 courses.
Spring
2039 W. North Ave.,, 773-395-7100, springrestaurant.netLight, Asian-influenced seafood starters and entrées (try the skate wing with cilantro-chili pesto) and outstanding vegetarian mains (like the salsify and caramelized-onion ravioli) make this a local favourite. A great date practically plans itself: Spring is only a few short blocks from nationally praised craft-cocktail lounge The Violet Hour.
Belly Shack
1912 N. Western Ave., Chicago, 773-252-1414, bellyshack.comDirectly under the Blue Line tracks of the El, this newly launched neighbourhood spot unites Chinese and Puerto Rican flavours in unexpected sandwich creations. Asian meatballs are packed with mint rice noodles in a satisfying flatbread pita, while huckleberry lime compote tops coconut milk “soft serve.” Curious, true, but their menu says it best: “U KUD LIK DIS.”
Hot Doug’s
3324 N. California Ave.,, 773-279-9550, hotdougs.comChicagoans sacrifice Saturday-afternoon hours, standing in the ice cold, to get into this down-to-earth joint. They wait for the best hotdogs in town – from the classic Chicago-style dog to inventive gourmet treats like foie gras and Sauternes duck sausage. Doug, owner and encased-meat mastermind, takes every order and is a helluva guy. Out of the way, but worth the trek.
Activities

istock / Patrick Warneka
Millennium Park
Located between Michigan Avenue and Chicago Harbor, Millennium Park is more an open-air museum than a green space, with its in situ sculptures, temporary works of art and outdoor amphitheatre designed by Frank Gehry. Whatever the occasion – attending a free concert, watching the distortions of the city’s skyscrapers in Anish Kapoor’s Cloud Gate or cooling off in the Jaume Plensa-designed fountain – a detour through Millennium Park is the best place to discover Chicago’s public art.
The Art Institute of Chicago – The Modern Wing
111 S. Michigan Ave., Chicago, 312-443-3600, artic.eduA 190-metre-long pedestrian bridge over Millennium Park leads visitors to the Modern Wing, where they can discover the Art Institute of Chicago’s collection of modern art in a newly opened space designed by Renzo Piano. The minimalist design contrasts with the more imposing Beaux Arts-style main wing. Home to a collection that includes works by Jeff Wall, On Kawara, Felix Gonzales-Torres and Carl Andre, the Modern Wing is a must-see for art lovers.
Museum of Contemporary Art
220 E. Chicago Ave., Chicago, 312-280-2660, mcachicago.orgWith avant-garde temporary exhibitions, a widely varied program including performances and an array of conferences on contemporary art, the MCA is more cultural hub than museum. Case in point: The first Friday of every month, the MCA is the destination for the city’s artistic intelligentsia, with a themed happy hour boasting a full bar, complimentary hors d’oeuvres by Wolfgang Puck, local DJs, creative spaces and the world’s only “iMac G5 digital dating bar” (whatever that is).
Wright20
1440 W. Hubbard, Chicago, 312-563-0020, wright20.comWright20 is an entirely new kind of auction house. In addition to the possibility of bidding on a work by Damien Hirst or a piece of furniture signed by Charles and Ray Eames, a visit to the adjoining gallery during the days leading up to an auction is a gives you the chance to soak up never-before-seen works from private collections.
Bucktown & Wicker Park
From the intersection of Damen, North and Milwaukee avenues, an assortment of trendy restaurants, boutiques, galleries and high-end apartments radiates from Wicker Park all the way to Bucktown. The area’s motley community, made up of students, artists and trendy young people, takes full advantage of the neighbourhood’s diverse offerings: You can pick up the latest Marc Jacobs creation or hunt for bargains in second-hand stores before heading to Spring for some foie gras gyoza or to Bluebird for Belgian-style braised rabbit.
Getting Around Chicago

From the ionic "L" trains to the masses of travellers passing through O'Hare, transportation defines Chicago. Since its early years as the America's stockyard city, both life and commerce here have been shaped by the city's unique position as a national hub for moving people and goods, be it by rail, road, water or air. Chicago is the only city in North America where six major railroads meet and nine interstates run through its suburbs. Its port is the most important on the great lakes and its airports is among the world's busiest. Truly, the crossroads of the continent are in Chicago.
Getting from the Airport
O'Hare is 27km from The Loop (the downtown core) and Midway is about half that distance. Chances are you'll be arriving at the much larger international hub, O'Hare, but transportation into the city is still pretty easy. Though cabs are plentiful, there are no flat rates – expect to spend about $35 to $40 to get into the city. The blue line of the "L" stops at O'Hare and at peak traffic times it might be the fastest way to get where you're going.
Taxis
Taxis typically aren't hard to come by in Chicago. There are 7,000 of them within the metro area and they're readily hail-able from major thoroughfares. The "flag pull" fee is $2.25, then it's $.20 for each additional 1/9 of a mile. Wait time is $.20 for every 36 seconds.
Public Transportation
The second largest system in the U.S., Chicago's CTA makes getting around on public transit a cheap and easy option. The famous "L" trains are the system's defining feature. The first elevated trains began running in 1892 and have since shaped the evolution of the city as the train's multi-coloured network radiated out from the core. The "L" now services 144 stations 24-hours a day, each one the hub of a neighborhood. The fare is $2.25.












