Chicago is one of the easiest towns to enjoy! There are so many things to do and see for free, I was surprised we didn't do more.
Recently we traveled to Chicago for my birthday and New Year's Eve. We really enjoyed the atmosphere of the city more than anything else that we took in while we were there.
After searching for the best hotel and the best deal, we ended up staying at the Best Western River North, on Ohio Street. The location was excellent. The indoor pool on the roof had an excellent outdoor gathering area, which would be perfect in the Spring and Summer. The restaurant and bar in the hotel, Pizzaria Ora, had better pizza than the famous Gino's East of Chicago. We experienced both while we were there. And also, the rates at the Best Western, were not ony unbeatable, but they also provided free parking. Considering most hotels charge a minimum of $20 per night, in the city of Chicago, this was another bonus.
The city is definitely a must, for anyone considering New Year's somewhere other than New York. If you get a chance, even if it's not on New Year's, Chicago is a must.
Here is a great article titled How to Visit Chicago on a Budget. I hope you can make it!