Please tell us where you live.

That would probably help, right? Haha We are in the northwest suburbs of Chicago.

Contact your local office of the University of Illinois Cooperative Extension Service about having a good reliable soil test for soil pH and major nutrients. Since UI does not do soil testing you will need to look at the labs they suggest. Then, using these simple soil tests, take a good in depth look at the soil you have to determine what else needs be done.
1) Soil test for organic matter. From that soil sample put enough of the rest to make a 4 inch level in a clear 1 quart jar, with a tight fitting lid. Fill that jar with water and replace the lid, tightly. Shake the jar vigorously and then let it stand for 24 hours. Your soil will settle out according to soil particle size and weight. For example, a good loam will have about 1-3/4 inch (about 45%) of sand on the bottom. about 1 inch (about 25%) of silt next, about 1 inch (25%) of clay above that, and about 1/4 inch (about 5%) of organic matter on the top.

2) Drainage. Dig a hole 1 foot square and 1 foot deep and fill that with water. After that water drains away refill the hole with more water and time how long it takes that to drain away. Anything less than 2 hours and your soil drainsâ too quickly and needs more organic matter to slow that drainage down. Anything over 6 hours and the soil drains too slowly and needs lots of organic matter to speed it up.

3) Tilth. Take a handful of your slightly damp soil and squeeze it tightly. When the pressure is released the soil should hold together in that clump, but when poked with a finger that clump should fall apart.

4) Smell. What does your soil smell like? A pleasant, rich earthy odor? Putrid, offensive, repugnant odor? The more organic matter in your soil the more active the soil bacteria will be and the nicer your soil will smell.

5) Life. How many earthworms per shovel full were there? 5 or more indicates a pretty healthy soil. Fewer than 5, according to the Natural Resources Conservation Service, indicates a soil that is not healthy.

Here is a link that might be useful: UI CES

I would not wait to plant, at least plant something to see how it does and get the soil working. You might be surprised.

Guessing you have clayish soil there in IL. What did you put down for mulch? It was a good idea in my opinion for a lot of reasons. If it's something durable like wood chips it will take a fairly long time for that to break down into the soil, so you'd have to rake it back to till in compost in the spring. If it's compostable mulch, like leaves, grass clippings etc., you might be able to dig it in in the spring and plant. If you can't 'fix' the whole place at once, start small and expand later. Mulches can enrich the soil as the microbes break them down and worms till in the organic matter.

You might want to get a soil test on a composite sample of untreated soil to see what you have. Your local ag extension office will offer that as kimmsr suggested.

I lived in DeKalb for a couple years, the soil was like black gold and I'd give anything for a truckload of that. :-]

Put pencil to paper

roundup and two weeks later roto till

plant and start amending this fall with organic matter

compo7, why wait until fall to add organic matter?

tox, I believe that Dekalb co. Illinois has been rated #1 for growing field crops, and Tipton co. Indiana has sometimes been rated #2. I am a county east of Tipton.

Thanks to everyone for all of your input! I still have time to decide, I'm sure everyone knows Chicago's been hit by a wave of cold and snow storms. I'm thinking your suggestions are great, I'll try to get some soil testing done, but start with some compostable mulch in the beginning of spring and plant some flowers and see how they do (thrive or die). Hoping I can get all the crazy weeds under control this spring, they were very rampant (think of thistle weeds taller than 5ft) when we moved in!