I've had seven flats in the last ten years. Once, I tried to call roadside assistance because it was supposed to be free, but they said they were going to take an hour and a half to get to me so I just changed the tire myself. Useless, and I was in Chicago too, you'd think in a large city they'd be quicker (it was a weekend non-rush hour before you ask).
7 flats that is crazy. I've had 3 flats in the last 45+ years and none in the last 20 years and average 20k miles/yr!
And that's even more than my rode touring bike