New Orleans by a mile. Bourbon, Tchoupitoulas, Royal, Burgundy and dozens of others are not only famous but require someone to know about history to give the correct pronunciation. Street names are lesson in American, French, and Spanish history in that city.
Madison, Wi has downtown streets named for early American historical figures. Names such as Washington are too ordinary and don’t give away the scheme. It’s the other historic figures whose names are largely overlooked such as Pinckney, Baldwin, Doty, or Bassett that fill out the street grid. Many were delegates to the Constitutional Convention and/or signed the Declaration of Independence.
As much as I hate to say it, it’s probably Salt Lake City. When you are given an address you can actually find where it is you want to go. You don’t have to “know” the city.
It doesn’t qualify as a major city but many of the streets in my old hometown of Plattsburgh, NY have women’s names. There’s Catherine Street, Cornelia Street, Margaret Street, Lorraine Street, Elizabeth Street, Helen Street, Caroline Street, Grace Avenue, Sally Avenue, Sandra Avenue, Sharon Avenue, Erin Avenue, and Marcy Lane.
The south side of Plattsburgh is the location of the old military base (Army, Navy, and finally Air Force). The streets in that area are named after states: New York Road, Arizona Avenue, Idaho Avenue, Nevada Oval, Montana Drive, Mississippi Street, Massachusetts Street, Maine Road, Kentucky Street, Louisiana Avenue, Connecticut Avenue, Iowa Circle, Illinois Drive, Indiana Drive, Kansas Avenue, Ohio Avenue, and Tennessee Road.
And there’s a little street called Ag Way because everyone loves a good farming pun.