I'm recently back from visiting Chicago, a city near and dear to my heart. There is so much to love about the city -- Lake Michigan in the summer, the Midwestern hospitality, the city's love of cured meats ... but I digress. Perhaps the most endearing part of Chicago is being surrounded by the beauty of the Chicago accent. Well, not everyone may find the accent endearing -- I first found myself put off by the accent when a pilates instructor told me to "challenge myself by pulling up on the bar" -- a literal sound minefield for a Chicago speaker. But now, years later I have come to hear the charm in the accent, and I hope that you will too.
Chicago is to my mouth a tough accent to master. Essentially a melting pot of sounds from the city's huge Irish, Polish, Serbian, Croatian, Italian, Ukrainian, and more recently Mexican and Latino populations, Chicago is a sprawling city with very specific North, South, and West Side sounds.
So in this sense, I'm not trying to detail a specific speaker, but rather a combination of sounds that I hear in most all contemporary speakers of the accent. Older residents or more stereotyped speakers may have other variations to their speech, particularly when it comes to turning a "th" into a "t" or "d".
Interesting to note that I have many Chicago friends who have modified their accent to sound more General American. However, after a few rounds of drinks those hidden Chicago sounds do start re-appearing!
So without further ado, the Chicago accent ...
1. Nasalization is Your Friend: If there is one thing to master when doing a Chicago accent, it's the accent's unique way of peppering nasalization throughout speech, particularly in words that end in "n" or "m" such as man, can, and, ham, etc. The real key to nailing a Chicago accent is finding the perfect balance of nasalization for the speaker.
2. Embrace the R: particularly at the ends of words such as far, bar, car, care, dare, and share! In Chicago a little R never hurt anyone's tongue, so don't be afraid to really engage the back of the tongue. This is similar to the General American sound, but don't be afraid to be even more R-generous than when speaking in GenAm accent. Think "Hard R!"
3. Tighten Up Loose Diphthongs: such as the sound found in "find" and "time". Instead of allowing your tongue to glide through the vowel sound, I feel the back of my mouth constricting a bit over the sound in order to get the desired Chicago "I".
4. Remember: "Flat is flat": Stepping off of the plane and into O'Hare airport, I was surrounded by Chicagoans looking for their "bags". Or "begs", rather. While they weren't completely saying "begs", there is certainly a flattening of the /ae/ sound in words such as have, had, flag, marry, etc. So flatten out that sound found in the word "flat".
5. Let Your Lips Kiss the "O": as in the words go, no, & Chicago. This is definitely a more "pure" "o" sound than say, in a General American accent, but don't go too hard on this sound, lest you want to end up farther north in Minnesota, Michigan, or Wisconsin. For this sound, I let my lips pure slightly to form the sound.
Bonus. "But Wait, How Do I Pronounce 'Chicago'?": Ah, my friend, this is harder than you think it would be. In contemporary, younger, educated speakers I typically hear "Chicago" pronounced with a middle vowel of "ah", as in FATHER, which is pretty much General American. Still, there are native speakers who may pronounce the city with some lip rounding over that "ah" turning it into a sort of "aw", although not to the extent of a New Yorker or Bostonian. Personally, I've heard this more in the Western suburbs (but that's just my experience). And finally, there are even native speakers who would pronounce the middle sound with a flattened "aa" (/a/). I found this more on the North Side, but again, only in my experience, as this is not a hard-and-fast rule. So there is no "right way" to pronounce the name of the city. My advice is to really research the character and make choices from there.
Other Thoughts: For many of the sounds above, it's imperative to embrace the Midwestern friendliness and give a little smile! Lip spreading is key to mastering the Chicago accent, and can help you shape the sounds.
And finally, perhaps the best Saturday Night Live Ode to Chicago (& yes, I've been to Ditka's):