There are only a few things to remember when you choose new images for your website.
Be authentic. Use images that speak about you, your brand, and your community. Try to avoid stereotypical images of Chicago. Instead, focus on the Community Areas, Neighborhoods and Landmarks that resonate with your target audience.
Your visitors are tired of cliche stock images that are too often seen in multiple places on the web. The last thing you want is an image that is also featured as a blog post and slider image on 10 other websites.
Here are a few great examples of images for a new website, or a redesign of an existing one.