Good stuff. Can you try #19 with a red star in place of the flag. Include silver into the scheme and use your Chicago font from #18, but all upper case. Also wondering what it would look like with CHICAGO in Blue Highway Lincocut.
Could you try outlining Chicago in two different ways on #23, one using black and one with red? And perhaps the same for #29, making Chicago silver and outlining it in both black and red?
Very good, thank you. Could we try it with Riot in the foreground on #33? Maybe move Chicago up just a touch so it's still overlapping, but not as much?