For a city/commuter an internal hub was my choice (nexus 8 speed) and it’s worked very well for my needs. For foul weather it would be even better!

The Linus Dutchi 8 is a little more than you want to spend (end of year prices could be better) but it’s a very well made bike ….the dealer locator shows a number of dealers in Chicago. You might look at one and see what you think.