Green’s Dictionary of Slang

artful, knowing; usu. as chickaleary cove, an artful, knowing, ‘clever’ fellow.

[1849		‘The Chickaleery Cove’ in Lacy’s Acting Edition of Plays [etc] 17: I’m a cheeky, leery cove, and make one, two, three].
1853		Morn. Post 30 Mar. 3/1: I’m a chick-a-leary cove / And she loves me too.
c.1864		A. Stephens ‘The Chickaleary Cove’ 🎵 I’m a Chickaleary bloke, with my vun-two-three— / Vitechapel was the village I was born in; / To catch me on the hop / Or on my tibby drop / You must vake up very early in the morning!
1877		Freeman’s Jrnl 19 Apr. 6/4: They are singing the ‘Chick O’Leary Cove at Weston’s Music Hall’.
1882		G.A. Sala in Living London (1883) June 242: The attributes of ‘Coster Joe’ and ‘Chickaleary Cove’.
1890		Sporting Times 22 Mar. 2/2: The bar appeared to be in charge of a chickaleary youth of uncertain age.
1892		in Punch 26 Nov. 252: With his thumb ’ooked orful hartful, and his chickaleary smile.
1893		Daily News 6 Apr. in Ware (1909) 72/2: The barrowman’s one aim and ambition is to be chickaleary.
1901		A. Binstead More Gal’s Gossip 149: When, in ‘a chickaleary tone,’ as you put it, you greeted your host with, ‘What-ho! This is where I draws the line at goin’ a-bird’s-nestin’!
1908		Wodehouse ‘The Guardian’ in Politeness of Princes [ebook] [T]he bit where Bob Whittaker beats the Eyetalian Gondoleery Cove.