I'm sure you know that most tomatoes you can buy in the average grocery store or fruit market have been bred to turn red when exposed to ethylene gas and to ship well, rather than for flavor.
There was a book earlier this year called Tomatoland which describes how and why commercially grown tomatoes have come to be the flavorless wonders they are today.
Many modern hybrids for the home grower have been developed for traits other than flavor--like short growing cycles, appearance, heat or disease tolerance, compact growth habit, etc.
Lots of the old heirloom varieties are extremely flavorful and are often quite tender-skinned. Many of them are downright unattractive, as they are prone to conditions modern varieties are bred to avoid.
I see that you live in "Chicagoland." If you live in the city, the farmers' market on Armitage east of Halsted on Saturdays has a farmer who grows and sells at least a dozen heirloom varieties at prices that are much more reasonable than I've found for fresh tomatoes at any of the other farmers' markets I've been to in the city. I've been on a quest for years to find tomatoes that taste like the tomatoes we grew at home when I was a kid and most of his varieties are wonderful. This year I got a community garden plot with a friend and we're trying to grow a few heirlooms but unfortunately the heat this year has caused a couple of the old varieties to drop their blossoms without setting fruit. It makes me want to weep every time I think about it.