After visiting a few good candidates in the downtown area, I found a membership rep that was (“willing to play ball”).

The gym was already having a “special” (aren’t they always?) and had dropped the initiation fee down to $99. I hate initiation fees almost as badly as I hate rent deposits. I let a few days pass, and the rep followed up with me. I told him how much I liked the gym, but that I was looking at several others. I offered to pay for the entire year upfront (they required a one-year contract anyway) if he could eliminate the initiation fee. Although he couldn’t technically eliminate it, he was able to cook the books to give me the same effect.

The end result? I ended up paying $150 less than if I had taken the existing offer. Not bad for a few minutes of conversation and a chance to practice my weak negotiating skills.

On top of that, I was able to get a “matinee” membership, thanks to my flexible work schedule. The only restriction is that I can’t enter the gym on Mon-Fri between 4:30 and 7:00 pm, which I couldn’t care less about. That alone saved me over $300 on the yearly fee.

A nice gym in downtown Chicago for less than $50 a month. Grand total savings: $450.