Race Options

I went ahead and spelled out dates, place, and cost (if there's more than one it's because it gets more expensive the longer you wait to register). I put them in order of dates. I checked out the one in CA that you said is your favorite-it is hilly and 90% unpaved trails, but their recommendation is to walk the uphills and jog downhill and flat areas. It looks gorgeous! I'll add pros and cons soon.

***edit: I've added approx flight costs based on a kayak search. Looks like it'll almost definitely be in the $300-$450 range no matter where we go.

***edit 2: I've added pros/cons for each

I think my top 3 are 1) Wildcat Canyon, 2) Windsor Green 3) Pensacola
Crescent City Classic
New Orleans, Louisiana 
April 7
$25/$30/$35
http://www.ccc10k.com/site3.php
$380 ORD to MSY
$400 CVG to MSY
Pros: fun city, new place, relatively inexpensive
Cons: early date

The 38th Annual Fiesta  10k/5k
Pensacola, Florida
Saturday, May  5
$??
$390 ORD to PNS
$410 CVG to PNS
http://www.pensacolarunners.com/?p=PRA_Events
Pros: beach vacation, more likely to have family support, see Jonna
Cons: not much info re: race, lame website

The Colorado Marathon
Fort Collins, Colorado
Sunday, May 6
$45
$400 ORD to CYS (hard to get to ft Collins-no major airport nearby)
$520 CVG to CYS
or
$300 ORD to DEN
$440 CVG to DEN
http://www.thecoloradomarathon.com/
Pros: downhill run, cool city, beautiful views, BIG event
Cons: hard to find lodging? No nearby airport, altitude?, katie's already been

Wildcat Canyon 10k
El Sobrante, California (30 min from SanFrancisco)
Saturday, May 19
$34/$39/$44
$360 ORD to SFO
$400 CVG to SFO
http://brazenracing.com/wildcat.html
Pros: gorgeous views, fun vacation spot, wine country
Cons: hilly/trails-may have to walk some of it (could be a pro), less family support 

Windsor Green 10k
Windsor, California (in Sonoma county 65 miles north of SanFrancisco)
Sunday, May 20
$40/$50/$60/$70
$360 ORD to SFO
$400 CVG to SFO 
http://www.windsorgreenhalfmarathon.com/home.htm
Pros: beautiful views, in wine country
Cons: farther away from San Francisco (a bit of a drive once arrive at airport), less family support