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It’s not clear from the story if this was a travelling companion or a stranger asked for directions.
Sorry, a stranger.

A complete and utter stranger.
If the first I’d have told them you’ll make your own way and see who gets there first.
Indeed.

If the second I’d have left them to their own devices.
In future, I may well do this.

After asking a rhetorical question (as to whether they believed Google maps, or the evidence of their eyes) I did tell them to suit themselves and withdrew from the exchange.
 
persisted in citing Google maps, adamantly insisting that this was correct, rather than listening to (having initially sought advice and answers) responses based on what eyes observed (what you could, and would see, in terms of desired destinations, at the following bus-stop), or what long lived experience had dictated how one could best interpret one's environment.

I live in a city a lot of tourists visit. I encounter similar behavior not infrequently. It's really strange; if you're so convinced your phone is correct, why did you ask me for advice? And people have to be pretty motivated to stop me. I don't look very approachable to strangers (even charity muggers tend to avoid me, ha!), walk at a brisk pace, and don't offer to help confused tourists on my own.

I'll be traveling to Chicago in two weeks, and will be utilizing the public transit quite a bit I presume. When I do, I definitely won't be relying on a GPS. I'll look at Apple Maps to see where the place is and which stops to get off at, but that's it. If I know which stops to get off at, I can use an official transit map to find the most efficient way to get there.

As a former resident of Chicago and frequent El rider, I'd say GPS can be useful when exiting an El stop. There aren't a lot of physical features (such as a mountain visible from everywhere or an isolated tall building) to help orient yourself, especially when leaving stops that are underground or don't have a view of the lake or river. On the other hand, most of the streets adhere to a grid system and street names stay consistent for miles and miles.
 
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