Green’s Dictionary of Slang

whirl n.

1. (US) a chance, an opportunity, a ‘go’.

[US]A.H. Lewis Boss 195: Every year it contributes to our various campaigns, say fifty thousand dollars a whirl.
[US]C.E. Mulford Bar-20 xi: Reckon I’ll hit th’ tiger a whirl.
[US]W.R. Burnett Iron Man 68: He was going to knock Coke flat in two rounds so he’d be sure to get a whirl at Mike Shay.
[US]Ragen & Finston World’s Toughest Prison 822: whirl – A trial or attempt; a ‘go’ at a crime.
[US]S.L. Hills Tragic Magic 197: Had many a whirl / with plenty of girls.

2. an outing (lit. or fig.).

D. Runyon ‘A Divorce Problem’ in Oregon Dly Jrnl (Portland, OR) 1 Sept. 7/1: She knows that I’ve worked a lifetime, and how I’m wantin’ my whirl.
[UK]Hall & Niles One Man’s War (1929) 295: One Cockney said [...] if he went out with the old ’oman and the little nippers and took ’em for a whirl over a ’oliday, he’d save nothing that week and go without his fags.

In phrases

do one’s whirl (v.)

(US) to serve a sentence in prison.

[US]Times (Wash., DC) 22 Aug. 15/6: I meets a boy in blue. I told him how it wuz, and got a wallop with the bat. He drove me over to the Irish clubhouse, and the whole thing fixed me up fer a month in the summer cottage. I couldn’t dig up, so I had to do my whirl.
give something a whirl (v.) (also give it a whirl, ...twirl, take a whirl)

(orig. US) to try something out.

[US]G. Devol Forty Years a Gambler 198: We will give him a whirl. How will we play him?
[US]S. Ford Torchy 140: ‘Seein’ it’s you,’ says I, ‘I’ll give it a whirl.’.
[UK]Wodehouse Damsel in Distress (1961) 104: ‘Well, it’s worth trying,’ said Reggie. ‘I’ll give it a whirl. Toodleoo!’.
[UK]Wodehouse Inimitable Jeeves 78: Going to give the nibs there the once-over [...] before taking a whirl at the Diplomatic Service.
[US]J. Lait Gangster Girl 42: I’m for givin’ it a twirl.
[US]H. Wilson ‘I Was King of the Safecrackers’ in Hamilton Men of the Und. 136: They agreed to give it a whirl.
[US]J. Weidman Price Is Right 9: Wapping asked them if they would allow him to take a whirl at a comic strip.
[US]P. Highsmith Two Faces of January (1988) 104: How exciting. Why don’t we give it a whirl tonight?
[UK]F. Norman Dead Butler Caper 145: ‘Let’s give it a whirl,’ I agreed.
[US]C. Hiaasen Skin Tight 48: Aw, let me give it a whirl.
[UK]Guardian G2 3 Aug. 3: But Mackay had noted something; he gave Lynam a whirl.
[NZ] McGill Reed Dict. of N.Z. Sl.