- Skyscrapers and speakeasies
- City life
- Lakes, lunching and lounging
Confident cloud-poking architecture, world-class shopping and a vibrant foodie scene make the Windy City trip-worthy.
The combination of glossy steel masterpieces and sprawling shoreline is simply seductive. A typical day will have you spinning the racks at the finest boutiques on the Magnificent Mile (a ritzy stretch of Michigan Avenue), cruising along the shores of Lake Michigan and tucking into gastronomic dish at a Michelin-starred restaurant in the chichi Gold Coast neighbourhood. Somehow Illinois’ biggest, brashest city manages to be cosmopolitan without being overwhelming. Rumour has it that some of the culinary world’s best and brightest use Chicago as their test kitchen before launching on a larger scale. Chef side-projects and specialty spin-offs of all flavours are the order du jour, such as Graham Eliot’s gourmet sandwich shop, Grant Achatz’s molecular gastronomic masterpieces at Alinea and TV personality Rick Bayless' streetfood-inspired Xoco. From all of the Michelin love annually bestowed on Chicago’s foodie illuminati, it seems their experiments are paying off.
The birthplace of the skyscraper – the first being the Home Insurance Building constructed in 1885 – Chicago has a riveting architectural history. Learn about the Wrigley Building, Tribune Tower and Willis Tower (formerly the Sears Tower) on an hour-long architecture cruise leaving from Ogden Slip at the Navy Pier (+1 800 595 7437; navypier.com). Study 40 steely constructions as you cruise the Chicago River, with an energetic guide in tow.
- You can easily flag metered taxis on the street; ask if they accept credit cards as not all do. You can hire a limo or car through Metropolitan Limousine (+1 800 437 1700 ; metropolitanlimo.com).
- Tipping culture
- Service charge is not usually included in restaurants and cafes unless you are dining with a large party. Doubling the tax is one way to ensure that you leave an ample tip.
- Siesta and fiesta
- Weekday evenings typically tend to wrap up on the earlier side around midnight, but weekends are fair game. Chicagoans start with happy hour around 530pm before dinner between 630pm and 8pm. The financial district is a ghost town after 530pm, but there are plenty of lounges and bars scattered around the city for the night owl. The Gold Coast and River North neighbourhoods, which are comparable to New York’s TriBeCa and the Lower East Side have chill low-lit lounges and bars.
- Packing tips
- They don’t call this place the Windy City for nothing. If you visit in winter make sure to bundle up and don’t forget the face cream – the whipping breeze coming off the lake can be harsh on your skin. In the summer, don’t forget your beach gear so you can flock to the shores of Lake Michigan like the locals do.
- Recommended reads
- Frank Lloyd Wright’s autobiography or commentary on his work such as The Architecture of Frank Lloyd Wright: A Complete Catalog by William Allin Storrer; Saul Bellow’s Adventures of Augie March; The Time Traveler’s Wife by Audrey Niffenegger.
- Regional specialities
- Deep-dish pizza is an institution. Try Pizano’s (+1 312 751 1766; pizanoschicago.com) on State Street, which serves calorific, but delicious pizza pies with butter-infused crust, tangy tomato sauce and bubbling mozzarella cheese. For a fully loaded Chicago-style dog and snarky service, head to The Weiners Circle (+1 773 447 7444), a hot dog stand in Lincoln Park. The surly staff are known for their sassy comebacks, so keep it simple and order your dog with ‘the works.’
- Time zone
- Central Standard; Time GMT -6
- Dialling codes
- US country code: +1; area codes for Chicago: 312, 773
- Do go/don't go
- The winter months of December to February are tourist-deterringly chilly, so if you can face the cold and just want to bounce from cosy bar to restaurant, make the most of the quiet. In summer (around July and August), the temperature is more cooperative, allowing for trips to the beach, breezy bike rides and sunshine strolls around the city. Unless you can really hold your Guinness, get out of Dodge on 17 March, when the St Patrick’s Day Parade snakes drunkenly through the city.
Don't go home without...
Strolling to Millennium Park to check out Cloud Gate, the enormous silver spherical sculpture by Anish Kapoor.