Obama's former home town has got everything you would expect from a metropolis and more. Some people would say it's like a mini New York, but more compact. Avoid booking your cheap flight to Chicago in the winter as temperatures can drop to a toe numbing minus 20 Celsius. Summers can be sweltering hot, but there is always the option to jump in Lake Michigan to cool off. There are many beaches along the shores. Try Oak Street Beach for a refreshing dip in the lake.The windy city has many historic neighbourhoods that are worth exploring on foot. Take a walk through Hyde Park, which is the area where the Obamas used to live before they moved into the White House. It's got a lively student vibe as it's home of the University of Chicago. Which means there is a wide variety of cheap eats and bars and cafes. Bucktown is another quaint area where you can easily spend an entire afternoon browsing the many independent shops. Prefer the high street brands? Try the shops on Michigan Avenue. For a bird's eye view of Chicago take the lift up to the observatory deck in the Hancock Tower. It may not be the tallest building in town, but it certainly has the best view. You can't visit Chicago without having tried the original deep pan pizza, which was invented here. Order one at Gino's East, an all time favourite even among Chicagoans.