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Chicago: What to Do in the Windy City

The so-called Windy City may often lose out to its big sister NYC in the city break stakes, but this Midwestern town has plenty to offer the traveller. From skyscrapers and art deco architecture to sublime eateries and hip bars, you’ll never have time to cross everything off your to-do list. 

By day, see and learn lots on a highly recommended architectural boat tour, or visit the Willis Tower for a stomach-churning view through a glass cube 110 storeys up; alternatively, visit the John Hancock Center downtown for equally awe-inspiring views. Try to time your visit with dusk to see sunset and the twinkly lights coming on all over town.

Art galleries abound. If you only have time to visit one, make it the Art Institute of Chicago where the numerous exhibitions could keep you occupied for an entire day (handy if that notorious wind is blowing outside), and you can have your own "Ferris Bueller's Day Off" moment. If the weather is fine, be sure to explore the surrounding park and take a photo of yourself mirrored in Cloud Gate, Anish Kapoor's wonderful giant polished "bean" sculpture.

For shopping, Michigan Avenue's Magnificent Mile offers plenty to give your credit card a workout, from department store staples such as Bloomingdale’s and Macy’s to independent stores and chic boutiques.

If you want to catch some sport, there is an abundance of animal-themed teams to cheer on. Check out the listings at Wrigley Field for a Chicago Cubs baseball game (you can also check out the White Sox at Soldier Field); see the Chicago Bears football team at the recently renovated Soldier Field; or the Chicago Bulls basketball team and the Chicago Blackhawks hockey team at the United Centre.

When your tum starts rumbling, you’ll be spoiled for choice with the vast array of eateries on offer. Head to West Randolph Street for the latest crop of buzzy dining spots -- just make sure you book a table three months ahead if you want to dine at one of the hippest new openings. Alternatively, settle for some of the famous Garrett’s popcorn -- the sweet and savoury combo sounds revolting but is as addictive as anything you’ll be offered on the slightly seedier street corners. 

If you’re looking to stay up late, there is a host of options, from late-night drinking dens and underground jazz haunts to blues bars and top-notch comedy venues. Best of all, the manageable size of the city makes most things walkable, so you can explore on foot to work off all those cocktails and dinners! 

Click here for our latest crop of Chicago hotel deals, or here for entertainment, restaurant and spa offers.

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Tips by

Deal Expert, London
Friday, 10 May 2013
See more Tips from
Amy Lindsay