I haven't tried that one but as was previously posted you have to take into account the fact that your southbound could be significantly late.
I tried the Wolverine 350 to Detroit and the 355 Wolverine back- I failed and spent the night in Windsor ON gambling, (with my wife's sarcastic approval- "I told you so...."). Turns out they are the same train: 350 turns in Pontiac for 355. I didn't realize this at the time but we were 15 minutes ahead, yes ahead, into Kalamazoo. A freight derailed ahead of us so they terminated the train Dearborn and bussed us to Detroit. When I tried to get a refund the agent told me that the bus could take me right back to Dearborn where 355 would start that day back to Chicago. In the end he took pity on me and changed me to 351 the AM Wolverine for the next day.
For my next trick: I took the, (reasonably), new 381 Carl Sandburg to Galesburg. It was late about 35 minutes. Inbound #4 the Southwest Chief, was not. I ended up with about 30 minutes to spend in Galesburg. That was a good day! (smirk)
Oh yea, I actually tried this one twice. The first time our P42 #128 died near Aurora, (BNSF/Metra). We sat for about 30 minutes until a yard job pushed us in to the Metra station. Fortunately I was able to secure a full refund and buy a Metra ticket home.
Keep researching- I do it all the time and bring a credit card, just in case.