This article is not meant to be an exhaustive exploration of mapping app accuracy, but purely some anecdotal observations that map errors exist all over the place.
Given the press and discussions about the Apple's new mapping app in iOS 6 and Apple's CEO recommending people use Bing Maps among others, I, of course, fired up my Bing Maps app on a friend's iPhone 5 and started panning around my neighborhood.
While the Bing Maps app is arguably the best and most mature iOS 6 mapping app right now, I still managed to immediately spot some errant labels: "Magnificent Mile" on Navy Pier, and "River East" on the Jardine Water Filtration Plant just to the north.
I think tourists and Chicagoans alike will surely agree that Navy Pier is indeed quite splendid, but the name Magnificent Mile is commonly reserved for that stretch of retail along Michigan Ave from the river up to about Oak St. Such upscale places as Tiffany & Co., Bloomingdale's, Nordstrom, Burberry, Escada, Coach, and Ermenegildo Zegna all pitch their storefronts along the Magnificent Mile. There's even an Apple Store!
MapPoint gets it correct. Although it doesn't have Magnificent Mile as a place or neighborhood, it does have three hotels with Magnificent Mile in the name. River East is centered on the area highlighted in yellow and you can see the piers on the right.
Regarding River East, first I wanted to look up the neighborhood boundaries, and to Bing Maps credit, the site "City-Data" does in fact include the Water Filtration Plant in their boundaries for River East. (!?)
This is clearly bogus however. The River East complex (which includes the River East Center condos and AMC River East 21) and the River East Arts Center are all outside City Data's boundaries to the south. And City-Data's boundaries don't even have River East along the river.
Again, MapPoint gets it correct. In a business search, it identifies nine locations including a gym, florist, etc. all along the river roughly bounded by Columbus and Lake Shore drives (and not including the Jardine Water Filtration Plant or Navy Pier).
So what does this tell you? Should you junk your mobile device and lug around a laptop with MapPoint installed? Well, no, but when the Intel Windows 8 tablets come out, MapPoint is an excellent and accurate source of "off-line" maps, and is a very capable business data visualizer to boot!