I must be missing something because I think it's (ignoring the fare, as you said) a plain old round trip because the point of origin is the same and the final destination is the same. I don't think the fact that there's a connection in ORD in both directions matters because it's just a connection.

I have one for you, tvl4free. I did this business trip itinerary in October and had an argument about ticketing with the company travel agent:

Oct 15: HNL-SFO (UA)
Oct 18: SFO-ORD-BOS (UA)
Oct 19: BOS-LGA (DL Shuttle)
Oct 22: JFK-SFO (UA)
Oct 23: SFO-LAS (UA Shuttle)
Oct 26: LAS-SFO (UA Shuttle)
Oct 28: SFO-HNL (UA)

What types of tickets was this trip? I thought (and priced it out this way) that I should have used an open jaw between HNL-BOS and JFK-HNL, with free stopovers in SFO. Then one-way DL shuttle ticket and a separate "inner" r/t between SFO-LAS. I priced the entire thing out at around 1600, before the company discount.

Company travel agent said I needed three separate "trips" because my way wasn't legal.

r/t HNL-SFO
open jaw SFO-ORD-BOS JFK-SFO (plus oneway DL shuttle)
r/t SFO-LAS

Her way priced out almost $300 more before discounts.

I think she was clueless because I was able to price it out my way on united.com.

Since it was company travel, rather than argue, I just accepted her way, but I think she wasted $300 of the companies money.

-David