What about going to a competitive city that will guarantee a routing through say ORD or DFW? I played around with a few queries on ITA and it looks like it's pretty trivial to do 4 segments on a saturday for low $200's AI ($50-55 / segment). Not great but you only need 13 segments so you could do this twice for less than $450 and then do a third run but squeeze in an extra hop in some fashion, like a STL-DFW-ORD-MKE-ORD-STL.

I only tried Aug 7 and just spent a few minutes on it so I bet you could find some better deals and routings out there, particularly later in the year.


St Louis, MO to Milwaukee, WI: 324 miles 3 hrs 25 min
American Airlines Flight AA1137 on a MD-80 (jet) in coach class
Departs St Louis, MO (STL) Sat, Aug 7 6:00a 1 hr 10 min
Arrives Chicago, IL (ORD) 7:10a
Layover in Chicago 1 hr 30 min
American Airlines Flight AA5002 on an Embraer ERJ-140 (jet) in coach class
(operated by CHAUTAUQUA AS AMERICAN CONNECTION)
(food for purchase)
Departs Chicago, IL (ORD) Sat, Aug 7 8:40a 45 min
Arrives Milwaukee, WI (MKE) 9:25a

Milwaukee, WI to St Louis, MO: 324 miles 3 hrs 30 min
American Airlines Flight AA5005 on an Embraer ERJ-140 (jet) in coach class
(operated by CHAUTAUQUA AS AMERICAN CONNECTION)
(food for purchase)
Departs Milwaukee, WI (MKE) Sat, Aug 7 12:30p 50 min
Arrives Chicago, IL (ORD) 1:20p
Layover in Chicago 1 hr 40 min
American Airlines Flight AA329 on a MD-80 (jet) in coach class
Departs Chicago, IL (ORD) Sat, Aug 7 3:00p 1 hr 0 min
Arrives St Louis, MO (STL) 4:00p