Depending on exactly how you define "distance" and "midwest," you might be interested in the Round-The-Bay race that is held just North of Toledo, OH in mid-June. It's 25-ish miles (don't recall the exact distance), and the start and finish are at the same place - no ground crew needed. Wind over the years has ranged from nonexistent to nuclear - though most years have been quite enjoyable. Great venue, great race, fun people, etc.