As a native (US) English speaker, I would say that the best translation for the Czech sentence is exactly what is shown at the top of the discussion: "What is that city like?"
Note the potential for confusion between the words "jak" and "jaky," the first meaning "how" and the second meaning "what" (or "what kind of," or "what is X like," depending on the context). Some translations here:
I'm curious, though, whether "What kind of city is it" would be accepted. Might try it if I see this again.
Better way to catch the reasoning of the phrase: jaky/jaka/jake all end up being a "how", or a "what kind" into the English translation. If you see "jake je to mesto", you can safely replace "jake" with "how". Afterwards, it's natural: "how is that city". Adding "like" to it follows naturally, since you are not asking about the current state of said city, but about its innate qualities: green, small, active etc. Nevertheless, jake -> how is the key here. It also works with "what kind": "what kind is that city" -> "what kind of city is that". Again, you'll get the innate qualities: large, busy, sleepy.