Sorry about your tomatoes. I have not grown too many in containers but the ones I did grow did not produce much. I suggest buying some that are especially suited for container growing instead of the larger varieties.

otomatoo - Sorry to hear about your problems there in "Chi-town". If you don't mind, I'd like to try and help. I need to ask some questions. I raise everything in 18 gallon containers and this year have harvested more than 90 pounds of tomatoes from my 19 "buckets". And the harvest of the "heavy beefsteak types is just getting started.

How large is the container?
How much direct sunlight each day?
What kind of "dirt" - Potting Soil or Potting Mix or ?????
What kind of plant - variety name?
How tall?
How much water each day?
Have you fertilized since planting?
Can you post a picture?

Even if you decide not to grow in containers again, let the rest of us learn from your experience.

I'm in Chicago also. My plants are doing fine in containers but the conditions are perfect for the dreaded spidermite. You might want to check your leaves under a loop or magnifying glass and see if you have these critters all over like I do.