What we like (16): Simplicity, font, scale, focus on "photo safaris" as opposed to "Chicago", idea of photos forming the compass outline
What we don't like (16): The compass. For some reason, this isn't resonating with us. We feel it's not representing the 3 main ideas we're trying to convey: photography (although the boxes forming the compass could represent photos), adventure / fun (although we do think it represents travel), education. The main reason, we think, is because you think of a compass when you need to find your way or when you are lost and we'd rather try to convey more of a fun, photography-focused idea. Also, the use of blue with the compass idea doesn't feel as strong to us as some of the other designs.
What we like (17): This feels like Chicago (reminds us of Chicago Cubs) which would resonate in the local market, simplicity
What we don't like (17): This one may not produce feelings of photography, adventure/fun, or education outside of the Chicago market. The outline makes me think of a compass (but I'm focused on this logo redesign) but we feel other people may just view it as a spiked outline without any context of what it could represent. Does the negative space in this one represent anything? It reminds me of what a lighthouse viewed from the sky may look like. We were just wondering if you had a specific reason for creating that negative space or if it represented anything to you.
What we like (18): Emphasis on photography. Anyone who knows about photography would understand the symbol represents aperture. Font.
What we don't like (18): Color: This combination doesn't resonate with us (sorry we can't be more specific on why... we just don't like it but can't seem to identify the reasons for it). The aperture symbol: Although this conveys the idea of photography, we feel it's a little bit too literal.
We really appreciate you submitting your ideas to the contest! (We hope we're not being too harsh or critical about anything; we're trying to be as clear and concise as possible about what we like and don't like to help everyone!)