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The Green Door Tavern in River North (676 N. Orleans, 312-664-5496) manages to walk the balance between classic tavern and tourist trap with aplomb. Housed in a 130-year-old wood frame building built shortly after the Great Chicago Fire (the last building of its kind built that close to the Loop) if you look at it hard enough you'll see that it has a noticeable lean..
The Green Door set up shop in 1921. The centerpiece of its main room is a Brunswick bar, one of the last made by the Chicago-based company before they shifted their focus to producing bowling alleys and pool tables. That bar still has a brass draught fixture and cash register, and is loaded with enough tchotchkes and memorabilia to rival a Bennigan's or T.G.I. Fridays. According to Sean Parnell's excellent write up of Green Door at his Chicago Bar Project website, the bar allegedly survived Prohibition as a speakeasy. one can assume that the six-foot high letters atop the building announcing its presence were not there at the time
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I walk here for lunch every now and then. Its decent enough, but the food is really nothing to write home about. Although the fried portobellos are pretty awesome as an appetizer.
Brunswick used to have a factory right across Huron where some pricey townhouses now stand. The building -- which had long since been converted into art galleries, studios, etc. -- burned down about 15 years ago. The fire consumed a whole city block and threatened to take The Green Door's wood frame building with it. That may be the fire that Sean refers to in his blog.
I've been here before, and while I pass it on the way to work every day, I'm ashamed to admit that I've never, ever noticed the lettering on top of the building.
I'm also in agreement with via_chicago about the fried portobellos. Yum.