Unfortunately it is possible. I booked a flight ORD-HEL-BRU with a 40 minute connection. I was hoping to miss it, next flight to Brussels was 7-8 hours later and I wanted to see downtown. Made it so quickly I'm not sure they were even boarding the Brussels flight when I got to the gate.

My research in advance did show lots of delays on the ORD-HEL route, so maybe I just got unlucky.