The prestigious Litmore Academy has sent its students on an extended field trip to Chicago. Among them are students Arisa, Gabby, and Brandon. Arisa- sweet, demure, shy, and lonely- is best friends with Gabby, one of the more well-known, garrulous, and fashion-conscious girls at Litmore. Lacking confidence in her- self, Arisa prefers staying in with a good book, but Gabby will have none of it and drags her out on the town. Which is where she bumps into Brandon, the cutest and most popular guy in school. Suddenly, the Windy City is blowing the winds of change...and romance...Arisa's way. Will she embrace them?