I'll snip this down to the parts I want to address.

1. Grachki (grach'-key): Chicagoese for "garage key" as in, "Yo, Theresa, waja do wit da grachki? How my supposta cut da grass if I don't git intada grach?"

Although the / k / of "key" does devoice the / j / of "garage," there is transitory voicing on the latter.

Herb:  One of the most widely taught myths of English phonology is that we have a contrast between voiced and voiceless in stops and fricatives (collapsing stops and affricates for convenience).  There are, however, a fair number of careful phonetic studies, including one I published in Word in 2003, that demonstrate that the contrast is really not one of voicing but one of consonant strength.  Fortis (strong) stops are aspirated initially in stressed syllables and may be glottalized in final position.  Fortis stops and fricatives also have longer duration than lenis consonants.  Lenis (weak) stops and fricatives are voiced between voiced segments including vowels, liquids (/r/ and /l/), and nasals.  Adjacent to a voiceless glottal state, which includes utterance initial and final positions, lenes are voiceless or may, as Melvin points out, show transitional voicing, voiced next to the voiced sound and voiceless next to the voiceless.  The consonants we're talking about are the class called obstruents, and English has no distinctively voiced obstruents, only conditioned voicing.  In fact, the voicing contrast is entirely redundant in English.

8. Kaminski Park : The mispronounced name of the ballpark where the Chicago White Sox (da Sox) play baseball. Comiskey Park was renamed U.S. Cellular Field (da Cell).

I have not heard this, or noticed this, myself, but I have no reason to doubt its existence.

Herb:  This nasal spreading happens because the syllable-initial nasal nasalizes the vowel, and a timing phenomenon can lead to an epenthetic nasal before the /s/.  It can happen even before an nasalized syllable, as in the fairly common pronunciation "ompen" for "open."

9. Frunchroom: As in, "Get outta da frunchroom wit dose muddy shoes."  It's not the "parlor." It's not the "living room." In the land of the bungalow, it's the "frunchroom," a named derived, linguists believe, from "front room."
 
Commentary on this "ch" will appear in note B below. Yes, it is from "Front Room," because the latter is what standard native speakers in Chicago also call what others call the "parlor" or "living room."
Note B:  /tr/ and /dr/ clusters before stressed, upper vowels /iy/ and /uw/ are heavily palatalized among many speakers, particularly males. In fact, there are male speakers who heavily palatalize /str/ under the same conditions, but I don't think the latter occurs in Chicago only.

Herb:  Palatalization actually fluctuates with retroflexion as the assimilatory mechanism.  You can also hear "structure" or "strong" with mid and low vowels respectively, at least in my Inland Northern speech, with a "hushed" /s/.  What happens is that the /s/ and /t/ anticipate the retroflexion of the /r/ and are pronounced with the tongue tip curled up slightly.  This gesture causes a different phonetic effect from palatalization.  You may be able to detect this if you contrast "shred" with "shed."  If you have a retroflexed /s/ in "shred," you'll hear a lower pitched oral turbulence caused by the fricative than with the palate-alveolar /S/ in "shed."  The palatal articulation pretty much fills up the oral cavity with the tongue and results in a very high pitched F2 resonance, the formant that most clearly reflects oral cavity size.  Retroflexion, because of the curled tongue, has a large oral cavity causing a lower pitched resonance.

17. Pop: A soft drink. Don't say "soda" in this town. "Do ya wanna canna pop?"

Herb:  Check the Dictionary of American Regional English (DARE) for extensive geographical treatment of terms for carbonated soft drinks. 
 
20. "Jeetyet?": Translates to, "Did you  eat yet?"  

you can find "pop" for "soft drink" and the collapsed "Did you eat yet?" in many upstate New York cities.

Herb:  Actually it's even more wide spread than that.  English speakers regularly palatalize /d/ before /y/, as in "did you" or "eat yet."
 
26. Expressways: The Interstates in the immediate Chicagoland area are usually known just by their 'name' and not their Interstate number: the Dan Ryan ("da Ryan"), the Stevenson, the Kennedy (da "Kennedy"), the Eisenhower (da "Ike"), and the Edens (just "Edens" but Da Edens" is acceptable).

Absolutely, on target, and that is the way all the traffic reporters on local television and radio refer to them.

Herb:  For years and years, no self-respecting Chicago Democrat called it the Eisenhower.  It's the Congress. 
 
Note C. This note addresses

                        "mare"in comment                                            3
                        "dror" in comment                                             24

Chicagoese indeed uses a single syllable where many others use two:

"drawer"            /drohr/
"mayor"             /mehr/
"prayer"             /prehr/

Herb:  Those varieties of English that have two syllables in words like these generally get the second by making the /r/ syllabic.  Final /r/ has the effect of laxing the preceding vowel, /ei/ to /E/, for example, so if the final /r/ is not syllabic but is rather that syllable coda, the vowel will lax.  I think the trigger is whether or not the /r/ is syllabic.

Herb

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