Yeah I live just outside Chicago in NW Indiana and it really doesnt get hilly until you get into my area and beyond. This is a pretty fair representation. Though to be far you probably should have removed Navy Pier and the Water utility (I belive thats what they do at the other one) pier.
The "Asian" architecture ruins the alleged "pub" for me. Typically you picture a pub being a small business inside a larger, possibly even 1x1 tile building. But maybe you guys have three story pubs in Great Britain ;-)