Guide to Chicago

Exploring the Windy City’s diverse neighbourhoods, from the Gold Coast to Magnificent Mile, is key to discovering what makes Chicago tick. (Please, don’t call it Chi-town.) Doug O’Neill helps you prepare for the perfect blend of sophisticated culture and Midwestern hospitality

STAY

Panoramic views & posh rooms are the stuff of Chicago hotels

ROOMS WITH A VIEW OR TWO

Bedding down for the night in a Mies van der Rohe building is part of The Langham allure. Rooms offer panoramic views of Lake Michigan and the Chicago River and there’s that 20-metre swimming pool. From US$383. langhamhotels.com

BOOK-LOVER’S DREAM Staying in the Author Suite on the 46 th floor of the Four Seasons Chicago means you have the hotel’s extensive literary collection all to yourself. The award-winning Allium Restaurant & Bar promises fine lobster nachos and a Chicago Dog “with house-made everything.” From US$358. fourseasons.com/Chicago

PORTABLE VIP Through the Keys to the City program, guests at the Peninsula Chicago get special access to VIP lounges in the city, personal tours of the Michelin-starred Grace Restaurant and are fast-tracked through museums and gallery lineups. From US$535. chicago.peninsula.com

EVERYTHING OLD IS NEW AGAIN Thanks to a $100-million renovation, the 434-room Ritz- Carlton Chicago has swapped its traditional design for a more modern vibe. Great views of the pier from the Rooftop at Torali bar or from a treadmill in the fitness centre. From US$329. ritzcarlton.com

MAKE IT A SPA DAY After a day spent touring the Windy City, spoil yourself with the Waldorf Cleanse in the spa at the Waldorf Astoria Chicago. Well-appointed rooms on the northwest corner of the hotel overlook the iconic Gold Coast neighbourhood. From US$375. waldorfastoriachicagohotel.com

EAT

Deep dish pizza is a must, but so are the award-winning eateries.

OH, FOR THE LOVE OF GOAT! Top Chef winner Stephanie Izard, who’s behind a trio of successful Chicago restaurants, serves up sophisticated takes on traditional diner food at Little Goat Diner. The Goat Almighty Burger includes pickled jalapenos and piri piri. Her other two restaurants are Girl & The Goat and Duck Duck Goat. stephanieizard.com

FROM A SOW’S EAR James Beard award-winner Jimmy Bannos, owner of The Purple Pig, has a thing for pork. Try the pork saltimbocca with prosciutto and honey or the sweet and crunchy pig’s ears. thepurplepigchicago.com

MICHELIN-STARRED DINING Chicagoans who’ve patronized Grant Achatz’s three-Michelin-starred Alinea now line up for the chef’s themed tasting menu at his latest eatery, Next. Insider tip: The prix-fixe menu costs less on weeknights. nextrestaurant.com

NO-FRILLS THRILLS BYOB. Minimalist setting. No coat check. The cooks at Michael Carlson’s 26-seat Schwa Restaurant serve your food. The menu changes every six weeks, but almost always includes the popular parsnip custard with candied sweetbreads. Book ahead. schwarestaurant.com

THE ART OF DONUT-MAKING How about a Whiskey Caramel Old Fashioned with Pecans? The Doughnut Vault specializes in artisanal donuts at its two locations (North Franklin and North Canal). doughnutvault.com

PREVIOUS PAGE: Chicago’s skyline reflected in the Cloud Gate sculpture by Sir Anish Kapoor. THIS SPREAD CLOCKWISE FROM TOP LEFT: The lobby of the Waldorf Astoria Chicago; dining at The Peninsula Chicago; the crunchy pig’s ear with fried egg by Haas and Haas; mille-feuille with caviar by Allen Hemberger; the terrace of Doughnut Vault; the lobby of the Langham Chicago.

THIS SPREAD CLOCKWISE FROM TOP LEFT: The interior of Violet Hour; a selection of cocktails from Scofflaw Bar; Carbon & Carbide Building (now Hard Rock Hotel Chicago); the essential Chicago Architecture Foundation River Cruise; the Jay Pritzker Music Pavilion; Chicago’s famed elevated trains; mixing the Juliet & Romeo cocktail at the Violet Hour.

DRINK

Chicago mixologists think outside the glass

A CHOCOLATE CHIP COOKIE WITH THAT COCKTAIL? Gin-infused cocktails rule at the Victorian-style Scofflaw Bar in Logan Square. Complimentary chocolate chip cookies are served at midnight. scofflawchicago.com

CREATIVE COCKTAILS IN FULTON MARKET If you’re thirsty and peckish in Fulton Market, The Aviary serves a five- or seven-course cocktail-and-food tasting menu that should satisfy both needs. Try the Scots Pine, a blend of yuzu citrus juice, elderflower and tequila. theaviary.com

BEHIND THE FAÇADE The James Beard award-winning Violet Hour Bar is dedicated to artisanal cocktails. Consider the Eeyore Requiem: campari, vermouth, Beefeater gin, Cynar, Fernet Branca and orange bitters. No cell phone use inside the lounge. theviolethour.com

WHEN THE SUN GOES DOWN Enjoy the sunset, drink-in-hand, at the Signature Lounge at the 96 th where a sprig of rosemary packs a wallop in the apple-spiced martini. signatureroom.com

SEE & DO

Impressionists, improv, innovative theatre & more

THE RIGHT CRUISE Riverboat cruises are plentiful. However, Chicago Architecture Foundation’s tours are led by specially trained docents who are well-versed in the architectural wonders along the Chicago River. architecture.org/experience-ca

HEIGHTS OF FANCY Catching the view from the Skydeck atop the 412-metre Willis Tower is a rite of passage for firsttime visitors to Chicago. Insider tip: arrive just before dusk to glimpse the cityscape at night. theskydeck.com

THEY’RE FUNNY THAT WAY Tina Fey and Steve Carell crafted their improv at the Second City Comedy Club in Chicago. For great sketch comedy, book tickets for Mondays at 8pm or weekends at 4pm. secondcity.com

GET YOUR GAME ON Wrigley Field encapsulates more than 100 years of baseball history. Remember that tours held on gamedays do not include a Club House visit. mlb.com/cubs/ballpark/tours

PLAN YOUR ART ATTACK! The Art Institute of Chicago is mammoth. If strapped for time, head directly to the Impressionist galleries. Expect fewer lineups at lunchtime and early afternoon. artic.edu

NOW FOR SOMETHING COMPLETELY DIFFERENT The Neo-Futurists have been performing fast-clipped experimental theatre since 1988. In their Too Much Light Makes the Baby Go Blind, the troupe performs 30 plays in 60 minutes. Oh, and your ticket price is determined by a throw of the dice. neofuturists.or