When you live in Chicago, sometimes you wonder how the city ever got the nickname "the city that works." We have two recent governors who served prison terms (one still serving), parking is ridiculously expensive, we make national headlines for violent crime and traffic stinks.
But when you need a taxi in Chicago, in most key neighborhoods, you just put your arm up. And even in the suburbs, or outlying neighborhoods, you can call a cab company, and a taxi comes, generally right on time.
Surprisingly, this isn't true in every major city. San Francisco, in many respects, is a much hipper city than Chicago. It's a cool coastal location that's the most expensive place to live in the country and a technology hub. It seems pretty sophisticated until you decide you are sick of riding the Muni (their excellent mass transit system that includes the city's famous cable cars).
It's nearly impossible, aside from very occasional taxi stands, to simply hop into a cab. And hailing a cab just isn't done in San Francisco. More frustratingly, when you call a taxi dispatcher, or use one of those new, cool taxi/limo mobile apps, there is still no guarantee that a cab will come. They'll take your reservation, but 15 minutes later you may get nothing more than an automated call, or text message, informing you that no cab or town car is coming. One town car driver was kind enough the last time I was in San Francisco to call me personally to let me know he'd rejected the reservation to pick me up.
"Huh!?" I asked.
"I'm not going to pick you up," he said plainly.
This is an open secret among San Franciscans. As a result, they are extremely helpful to all visitors riding on the Muni. They'll help you pick the best stops, or make transfers, or even handle luggage--a true testament to the good heart of the city. But it's also because they know the Muni is kind of the only way to go in town. Ask and they'll tell you--taxis don't always come, and they're hard to come by.
And that's one way Chicago, a city with many flaws of it's own, truly works in comparison.