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We don't preface highways with I in Chicago. We either just use the number (I took 290 to 294 to 88), or we use their name. Sometimes we use a combination (I took the Eisenhower out to the Tri-State and then to 88).

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That works because Chicago is in the north central part of the country, where highway numbers are firmly in the double digits. In the southwest the numbers are often single digit, so it's awkward and confusing to use without a preprended "I-" or "the".

I think it's triple digits that become a mouthful with the "I-" prefix. Double digits sounds best with the "I-", I think.

Triple digits come from being a spur of a two-digit highway incidentally, not to do with region. I-385 is a spur of I-85, etc.

To ultra-pedant it up, generally only odd prefix digits indicate a spur (only connects to the prefixed highway in one spot), where even numbers indicate a bypass or beltway (which intersect the main highway multiple times).

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