A FlyerTalk Posting Legend
Join Date: Sep 2009
Location: Minneapolis: DL DM charter 2.3MM
Programs: A3*Gold, SPG Plat, HyattDiamond, MarriottPP, LHW exAccess, ICI, Raffles Amb, NW PE MM, TWA Gold MM
Posts: 100,407
If you take the train, wouldn't more time be required to get to T5? Even before the move, it was a hike from the ORD train stop to the DL check in counters and security checkpoints.
My vote is that OP would need to be incredibly lucky for this to work, assuming that the flight is on time.