Since I posted, things have changed a bit. The routing can be a simple SFO-ORD-BOS-SFO routing. But they need about 12 hrs in ORD. There'll be four people traveling - two paid and two on an award. Domestic saver award because the two on award are tight on cash (students) but have 60k miles each.

If a 12 hr stop in ORD is not permissible under the rules, i can try convincing them to take an award SFO-ORD-SFO and pay for the ORD-BOS-ORD RT.

Ideally i would advice them to avoid ORD on the return if at all possible.

Travel time is in the last week of June, first two weeks of july. typical summer travel. probably higher fares because of summer travel too.