American Airlines has a low $126.20 round trip fare between San Francisco SFO and Chicago ORD for departures from late September into November. These are nonstop flights, mostly Tuesday, Wednesday and Saturday.
Of course you can fly one-way for only $63.10 in either direction.
This route is challenging Frontier Airlines $49 one-way fares between San Francisco and Chicago.
Los Angeles, where Frontier has fairly wide open $39 one-way fares, has one-way LAX-ORD for $40.10 for the first three Wednesdays of November, but the round trip fares are generally higher, if originating at LAX. If starting in Chicago you can fly ORD-SFO-ORD for $80 round trip leaving Tuesday and returning Wednesday during the first weeks of November. Saturdays are $79 one way for a few dates.
American Airlines Chicago ORD – Los Angeles LAX
$80.20 Tuesday, November 3 – Wednesday, November 11
Flight Miles = 3,489 miles in economy O class.
American Airlines San Francisco SFO – Chicago ORD
$126.20 Saturday October 3 – Saturday October 10
Flight Miles = 3,692 miles in economy O class.
American Airlines San Francisco SFO – Chicago ORD
$126.20 Friday November 6 – Saturday November 7
Flight Miles = 3,692 miles in economy O class.