Da Chicago inflection is often imitated but just about never properly annunciated. Here is my small breakdown of how to talk like dem guys in Chicago, ovah by dere.
ANNUNCIATE"S"s are generally hissed or prolonged, especially at the end of words.
"Gesssssh, dissss knucklehead again." or even "Da busssdrivah taken dat asssss to ssschoo."
Over emphasize all "D"s at the start of words, and while you are at it take every "TH" and switch it to a "D". Like, " Oh ya, u'se talkin about d'ose ddudesss ovah by d'ere.
There: D'ere
Those: D'ose
and so on...
The true keey to talking like a Chicagoian is knowing how vowels are pronounced.
Basically every vowel turns into an "A" however there are three "A" sounds in the Chicago vernacular Think of the words Cot, Cat, and Caught; they all sound the same but are pronounced differently "Cahht" "Caaaat" & "Cawt".
If you ever find yourself stalling and confused on how to say something just turn all the vowels in the word to flat "a"s. This isn't proper Chicagoese but it's close.
COMMON TERMSAf:
of
Ahlla:
All of, not to be confused with Allah.
AL-OH:
Hello; especially when answering a phone. "Al-Oh diss is Pequod's, whaaaat caneye get fahya"
Braaat:
Bratwurst
Brewski:
Beer. Actually almost anything can have a -ski suffix. It's a joke based on a time when Chicago had more Polish citizens than any city in Poland, even Warsaw! Here's a decent example of abusing the -ski "Aye broski, grab dem keyskies for da carski and we'll goski."
Cahmbo:
italian beef sandwhich and italian sausage sandwhich combined to create 1 mighty chicago-sammich.
Canna:
Can of. "yo pass me a canna oldssshtyle"
Cuppa Too-Tree:
A couple, two or three; a few
Chicaaaago Dahg:
All beef hotdog on steamed poppyseed bun.
Chicago Style
Means "the works" or "everything"; yellow mustard, bright green relish, onions, tomato wedges, pickle spear, sport peppers and celery salt.
Da Wahrks:
See above "Chicago Style"
Dahg:
how to pronounce "hotdog". "We'll take 2 Chicaaago Dahgs withda werks."
Didkah:
Mike Ditka, greatest coach of all time. "okay how abawt Didkah vs. 12 Mexicans with da Swine Flu?"
Goes:
Said or Say. "I goes, "Aye ef u brah!". and den he goes, "no, ef U, braaaah!"
Guys:
Group of people regardles of gender. "Use guys go find da line fo da ladies room, imma piss right 'ere.
Flip-a-bitch:
U-Turn
imma:
I am about to.
Jeetyet:
Did you eat yet
Jewels:
Jewel grocery store
Ketchup:
For french-fries and children.
Knucklehead:
Simalar to shit-head, with the difference being their stupidity generally starts fights.
Ovah by Dere:
A location. "U'se know UIC, right? Well use take Taylor west 'bout too-tree blocks and it'll be ovah by Dere."
Pahp/pap:
Softdrink. Chicagoians don't drink cola or soda, they drink pop, yet they pronounce it "pap" or "pahp", when eating chicago deep-dish, the pop of choice is Grape.
Relish:
Chooped up neon green pickles. Classic Chicago Dogs have bright green relish. Other relish is used at times, but then the dog is not authentic. Fluky's is the originator of the relish.
Rahsen's:
S. Rosensbun. Bun of choice for hotdogs is S. Rosens, also pronounced with an "a", "Where are yah Rahsen's located?"
Sammich:
Sandwich.
Sassage:
Sausage
"Snaaap":
Snap. It is extremely cool to speak about the sound a Chicago dawg makes when yo bite into it. "aye gawddaaamn right, I love d'at snaaap sound from my dawg"
Tree:
Three. The number between two and four.
U'se:
You all, or y'all. As in "Where u'se bastards goin?"
Viennaaa:
Vieana dog of choice. it's made in the city. You don't buy another cities dog, as of recent a company called "Red Hot Chicago" has hit the market.
Yeaaah-sure-guy:
Time to shut up. This is a new classification of a word. Not a noun, verb, or whatever, it's an interuption. "Yeah-sure-guy" is often said when a bitch is talking that is in need of taking a seat. "Yeah-sure-guy" sounds the best when pronouncing as one syllable.
I'm sure I missed a ton so feel free to add your own.