Even though walking through campus will be a pain once the snow hits, at least we have the content feeling of being merry in our hometowns for break! I live in Crown Point, IN, I love being home for the winter. There's a lot of nostalgia to being back with your family during a really cheery time of year. I'm also lucky enough to live relatively close to Chicago, and get to experience the magic of one of the best cities during Christmas time.
I could go on and on about the holiday's and not just because I can completely slack off from school (thanks to the end of the first semester). I thoroughly enjoy going into the city during winter despite how unbelievably cold the wind chill can be. I think it's just the feeling of being completely happy and content with the holiday season, and being able to experience that bliss in Chicago. My personal favorite, but my fiancé's worst nightmare, is skating in Millennium Park. It is probably the most stereotypical thing to do in the winter, it is a necessity if you're visiting the city. If you're a thrill seeker though, definitely go check out the ice skating opportunity at the John Hancock Observatory, it currently has the highest ice skating rink in the world!
I could also go on and on about where to eat in the city when you visit, but I will always choose pizza (Gino's east or Lou Malnati's). I could also tell you that you should also go visit the lights at Lincoln Park Zoo. It's definitely something to 'ooh' and 'ahh' at. Macy's on State Street is also a good way to kill time before grabbing your dinner. You can check out their amazing window displays along with checking out some restaurants (you can never eat too much during the holidays).
If I'm not stereotypical enough already, if you end up going into Chicago with your significant other, definitely try out a carriage ride! I have personally yet to do it, but everyone says it's great at night with all of the lights around town. That leads me into another great point: check out the Christmas tree in Millennium Park because it's so gorgeous.
You can also go check out all the museums and their Christmas themed exhibits, walk around the lake when it's iced over (it's so cool looking), and you can also go to Navy Pier! If you're of age and go to IU you should also go to Kirkwood bar (it's where all the IU people meet up) a great tribute to a great university!
If you decide to not go to the city around Christmas time, you can definitely still find joy in your hometown. I know that Crown Point will always be a comfort during the holidays, and you can't beat coming home from school to spend a much needed break with friends and family!