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My kind of town


Chicago, the USA's third-largest city, is where skyscrapers were born. It's home to deep-dish pizza, Barack Obama, jazz, the blues, the finest Impressionist collection outside Paris and 24 public beaches along 26 miles of Lake Michigan shoreline. By Mike Gerrard



Trump International Hotel
If you recoil at the name of Trump, a stay in the laid-back luxury of the tasteful Trump Hotel in Chicago might give you second thoughts. Its Michelin-rated restaurant with stunning floor-to-ceiling windows and the Rebar lounge bar with equally impressive city views are just two highlights.; 401 N. Wabash Avenue.


Palmer House Hotel
In business since 1873, a stay here is steeped in history and grand design. Expect to see architecture tour groups standing open-mouthed in the lobby, though a recent modernising make-over keeps it current as well as classy;; 17 East Monroe Street.




David Burke's Primehouse
This is no ordinary steakhouse. Chef David Burke is so into steak that he owns his own prize bull, and the restaurant has an ageing room on the premises. His 75-day Ribeye was voted Best Steak Ever by the TV Food Network'.; 616 N Rush St.


Gino's East
My number one stop for the city's signature deep-dish pizza is Gino's East on Superior, whose graffiti-covered walls were so essential to the place that when they moved location a few years ago, they took the walls with them. Decidedly delicious deep-dish;; 162 E. Superior St.




Billy Goat Tavern
Every city has its version of the Billy Goat Tavern, a dive bar where politicians and journalists drink together (it's close to the Chicago Tribune building). It was called the Lincoln Tavern till a billy goat fell off a passing truck, wandered in, and was adopted.; 430 N. Michigan Ave.


Dry Hop Brewers
Chicago's having a craft beer boom and one of the best new brewpubs is DryHop in Lakeview. They love to experiment and brewed 60 different beers the first 10 months they were open. How about a hibiscus and orange schwarzbier? Great bar food too.; 3155 N Broadway St.


The Signature Lounge
It costs $18 to visit the John Hancock Observatory, now confusingly renamed 360 Chicago, but for $14.50 you can sip a Skyscraper Cocktail in the 95th-floor Signature Lounge and still get those genuinely breathtaking Chicago skyline views;, 875 N. Michigan Ave.




Arts and Artisans
This Chicago arts and crafts specialist has four locations in the city where you'll find exquisite jewellery, ceramics, glasswork, wooden carvings, vases, clothes, accessories and all manner of other gorgeous things from over 400 American craftspeople and 50 jewellery designers;, 321 N. Michigan Ave.




Bike and Roll Chicago
Do what the locals do and enjoy that lengthy lakefront. You can walk or jog but lots of people ride bikes to take them out to the beaches along the 18 miles (29 kms) of car-free bike paths. Bike and Roll Chicago does bike tours but also has four rental locations along the lakefront;


Buddy Guy's Legends
Buddy Guy is a legend and at his blues club he showcases other blues greats and up-and-coming local musicians. Stars like Van Morrison, The Rolling Stones, Bo Diddley and Willie Dixon have all graced the stage. You cannot visit Chicago without hearing some live blues and this is the place;; 754 S. Wabash Ave.


Velvet Lounge
One of the best jazz lounges in the Windy City was opened by local sax player Fred Anderson and though he died in 2010, his legacy lives on. Check the calendar, though, as they also have comedy and hip hop nights.; 67 E Cermak Rd.




Absolutely Chicago Segway
People don't expect a big city to have so much waterfront and a great way to explore Chicago is on a Segway Tour that takes you along the shoreline of Lake Michigan and through the city's lakeside parks. Absolutely Chicago Segway has other fun options too, like haunted tours and gangster tours;


Chicago Architecture Foundation Tours
The name may not be snappy but everyone I've told to go on one of the Architecture Foundation's tours has loved them. Walking tours take you into hotel and office lobbies but best of all are the Chicago River boat tours for an overview of the city's fascinating history and best buildings;


Chicago Detours
Amanda Scotese runs tours that are definitely different. Her Historic Pub Crawl covers the city's best bars, while her Jazz, Blues and Beyond Tours take you into hardware stores with hidden music stages and will have you learning harmonica from a Chicago blues musician who hops aboard the bus;


Art Institute of Chicago
Don't miss the Magritte exhibition at the city's most famous museum. Magritte: The Mystery of the Ordinary, 1926–1938 runs until October 13 and is the first major museum show to focus on the artist's most profoundly inventive and experimental years, featuring over 100 paintings, collages, drawings, and objects, along with a selection of photographs, periodicals, and early commercial work;

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