Recommendations for 2.1 speakers, budget $500

if you ever plan to upgrade to 5.1 or 7.1 in the future, you should invest in a receiver

as for speakers.. there's a lot of good ones in the <$500 range

unless the speakers have built in amps (i.e. "active" speakers) then you will need to provide some form of amplification.

I would grab an inexpensive used receiver off craigslist, and then get a sub and a nice pair of bookshelf speakers. Any requirements in terms of size (e.g. tower vs bookshelf vs small satellite) or aesthetics (black vs wood color) etc?

Those Energy Minis don't look bad but I think you can do better than that pioneer receiver. You can find pretty good receivers on craigslist for around $100, just keep looking. I live around Chicago too, and I look at the Craigslist electronics section every few days for the northwest suburbs to see if there are any steals, and I usually see some great deals for receivers and amps. Subwoofers can eat up a lot of your budget fast, so what you might consider is getting full range speakers for now, with the option of getting a sub later if you decide the bass isn't enough for you.

Here are some options for full range speakers which I think look good in your price range:
BIC Acoustech PL-76
BIC Acoustech PL-89
Infinity Primus p362
EMP Impression E5ti towers
Elemental Designs A6-6T6 tower speakers
TSC TST2 towers

There are some good speaker/sub combos that might fall on your budget though. Some subs you should check out are the BIC Acoustech H100 and the Hsu Research STF1 (there's a pretty good sale on that one right now). Some decent and inexpensive bookshelf speakers which could go well with those are the Hsu HB-1s, The SVS SBS speakers, the Tweakcity WAFs, the TSC TSBL 6.5s, and the Infinity Primus P162.

Those speakers in the 2nd link were Energy RC-10's not RC minis so that was a pretty good deal!

You should check out a place called Saturday Audio which is in Chicago. They have deals on PSB speakers which you can get in light colors like maple.
http://saturdayaudio.com/
http://saturdayaudio.com/picturepage...9-2009.htm#B15

You should be able to get 2 bookshelf speakers there for $300 and then find a decent receiver or craigslist for cheap.