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Hip, sophisticated and full of colors, a visit to Chicago, also known as ‘the Windy City’ will be cherished for a lifetime. Browse the amazing museums and art galleries. Visit exciting historic and cultural attractions. Go shopping, chill out in cool cafes and dine in award winning restaurants. Chicago is an amazing destination to enjoy a vacation full of romance and fun. Save more on airline tickets by booking cheap Chicago City flights on OneTravel. We offer exclusive deals on top airlines including AirTran Airways, Delta Air Lines and United Airlines. The average flight time from Boston, MA to Chicago, IL is around four hours, including layover time.