Run! It's a gargantuan chihuahua!

Could the dog look happier? Mouth open, tongue out, suggestion of smile? This guy looks lonely.

Outlining everything helps unify the logo, but has turned it into a unified jumble. Maybe "Chicago" is solid?

Can't decide if I like the perspective effect. You've got a lot going on already (different typefaces, mixed case, dog intruding into the type) that it might work better without it.

Marc,

I agree on the facial expression and type outline. Thanks for the input.

t

I would add a serif and make it a capital I. For the outline, just fill in all the holes with black and it will be much clearer.