It's hard to say if raising your rent is possible or not without knowing specifics about the property and what you're currently getting.
As far as Hyde Park goes, the rental market appears to remain strong, and the residential real estate values are holding up well given the overall market conditions in Chicago. This is likely due to the fact that Hyde Park did not experience the same rapid appreciation as the surrounding areas. That said, we are seeing moderate price declines over the past year.
From May 1-August 30, 2008, Twenty 3BR/2Bath Units sold. The average closed price was 278,906. The average list was 292,810. Market time averaged 164 days.
For May 1, 2009 - Today, Six 3BR/2Bath units have sold, with Three closings. The average closed price is $277,333. The average list is $286,500. Market time is difficult to determine currently as the sample size (3 closings) is unreliable compared to last years volume. Should have a better idea of Market Time at the end of August.
Needless to say, there are many fewer buyers out there this year. The ones that are recognize Hyde Park as a value and are willing to pay very close to last years price. Hyde Park also has a very low foreclosure rate when compared to the city, which would indicate that on average there are less sellers in distress and prices will be supported when this is the case.
Hope this helps, feel free to contact me with any questions.