These are amateur calculations so there may be a bit of error.
The highest altitude above average terrain you could put an LPFM antenna with 2 watts would be 942 feet.
The highest altitude above average terrain you could put an LPFM antenna with 1 watt would be 1476.
(The rules and regs state that 450 meters is THE MAX! (1476 feet)
The FCC will not license LESS than 1 watt.
When you say 2 watt translator is covering Chicago, you may have to define Chicago (City limits? Suburbs?)
And then, what is coverage? I can listen with my Walkman portable? I can listen at the far reaches if I use my car radio? Or: I can pick up the 2 watts if I have an external antenna up above my roof-top connected to a very sensitive receiver.
I think we are totally talking theory here. I ran a search using the RecNet frequency finder and you are not going to get an LPFM frequency in Chicago. I asked the search to assume they do away with the 3rd adjacent channel problem, and that they assume all the translator invasion frequencies just go away, etc. etc and the computer still said: No, there is NOTHING available in Chicago.
An if you could get a frequency, could an LPFM afford the rent for an antenna on a building at 1450 feet?
The FCC's intention is that the primary coverage area for an LPFM would reach out a MAXIMUM of 5.6km which translates to 3.48 miles.
I was in a town this week that has an LPFM. I wanted to see it but IT IS NOT where the FCC records show it to be. (tsk, tsk, shame, shame) As I drove through and across town, I was able to pick it up on my car radio for about 7 to 8 miles... which means it had an effective range of about 3-1/2 miles.