Chicago Destination Guide

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Everything is big in Chicago, from towering skyscrapers to voluminous Lake Michigan and the city's wildly diverse range of entertainment. Unofficial capital of the Midwest and regarded as the 'second city' of the United States, this bustling metropolis has the capacity to overwhelm. The best response is to simply breathe in, steel yourself and experience Chicago tourism like a local – with a hot dog in hand and a spring in your step. From the soaring Willis Tower to The Loop and historic Wrigley Field, a trip to Chicago is bound to leave a lasting impression.

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Chicago's bustling city centre is clustered around The Loop and the adjacent Near North and Near South neighbourhoods. Many of the city's most popular attractions are based in these three neighbourhoods, including the Art Institute of Chicago – home to Edward Hopper's Nighthawks and Willis Tower, which was once the tallest building in the world. Outside of The Loop, many of the most popular things to do in Chicago can be found in the suburbs. The well heeled North Side is home to lively pubs and clubs, the West Side is a trendy hipster enclave while the South Side is where you'll find Chinatown and some of the best food in the city.

Eat and Drink

Diet-conscious diners beware, Chicago meal portions are huge! If you're looking to partake in some gastronomic gluttony you can't turn down a genuine Chicago hot dog with all the trimmings, while another local favourite is an authentic Italian beef sandwich. The South Side is the best place to sample the fried chicken brought to the city by the thousands of African American migrants who migrated north during the 20th Century. Don't forget some of the best restaurants in Chicago are actually out in the suburbs. The same goes for the city's bars, the best of which are clustered around bohemian Wicker Park and nearby Logan Square and Bucktown.

Where to Stay

Chicago hotels are predictably diverse in range and number. Many visitors aim to stay near the Magnificent Mile, the major thoroughfare which runs through The Loop and into the upscale Gold Coast neighbourhood and takes in portions of the picturesque Chicago River. There are fewer options on the Near North Side, however bargains can still be found around the outskirts of The Loop for those determined to hunt one down. Numerous hotels are located far out on the northwestern edge of the city near O'Hare International Airport. However, they're well worth avoiding unless you want to endure an almost hour-long train ride into the city.


Most visitors come to Chicago to admire its stunning architecture and experience its lively cultural and entertainment scenes. However, Chicago shopping is just as first-rate and the best place to start is on The Magnificent Mile. Many of the city's most popular shops are located along this mile-long stretch of Michigan Avenue, while just around the corner is the similarly trendy Oak Street. Macy's flagship Midwest store is on State Street in The Loop but if brand names don't interest you, simply head out to Lincoln Park, Lakeview or Wicker Park to experience some of 'the Windy City's' best boutique shopping.

Chicago like a Local

When the Chicago weather warms it means only one thing: baseball season. No trip to sports-mad Chicago is complete without soaking in the summer sights and sounds at the ballpark. The city's beloved Chicago Cubs are based on the North Side and play out of historic Wrigley Field – one of world sport's most famous venues. The South Side is home to the equally popular Chicago White Sox. Their US Cellular Field home is a modern stadium but the Sox have plenty of history, having played in the city since 1900. Even if you can't get tickets it's worth heading out to the bars and clubs around the respective grounds simply to soak up the party atmosphere.