Perhaps a better comparison to Quantrill in terms of bloody ruthlessness would be John Brown, since both men were active in the same regional conflict. Brown's abolitionist buddies in the northeast, of course, undertook some dirty political and electoral tricks of their own, in an effort to tip the election in Kansas to the anti-slavery side.
An 1850s version of Chicago politics probably would include the arming, provisioning and transporting of "new voters" to any place (like Lecompton, Kansas, for example) where an agenda must be advanced by any means necessary.
I think that it was the pro-slavery side that was sending men from Missouri across the border into Kansas to vote that caused Congress to refuse the first Kansas constitution. The Northerners who settled there, had in fact settled there permanently.