Dive Right In

From time to time, Maureen and I talk about traveling, and all the wonderful places we plan to go.  Ok, so we talk about it quite often.  We had our honeymoon trip to Ireland, and this December we are going back for my mom and dad’s 50th anniversary.  We are also trying to figure out if we can do a layover in Madrid either before or after the Emerald Isle.  We have talked about trips to France, Germany, Italy and Greece just to name a few.  But seeing as a winning lottery ticket has yet to cross our path, it may be years before we see all the places we want, so in the interim we try to find our own little adventures right here in the city of Chicago.  This past Friday night, it was The Best Dive Bars in Chicago Pub Tour put on by the good folks over at The Chicago Historical Museum.

The Chicago History Museum Best Dive Bars in Chicago Trolley Tour

It is a trolley tour that lasts about three hours, with four stops along the way.  Between stops, the guides provide information about the history of each dive, and general information about Prohibition and Chicago history in general.  Unfortunately, the half hour time allowed at each stop gives you just a taste of each bar, but I guess that was the intent of the tour to begin with.

In my opinion, the only true Dive on the tour was the very first stop, so I am going to save that one for last.  Our tour ended at an interesting but way too overcrowded place called Old Town Ale House.  It is probably a lot more of a dive on the week nights, but considering the place was packed before we arrived, the addition of our thirty drunken trolley mates added a few too many bodies to the mix inside the small space.  A long favorite of Second City alum, the colorful artwork and dark atmosphere really define the joint as a dive, but it’s popularity as a dive really precludes it from being a dive at all.

Maureen and I with our Trolley mates Mike and Jamie at the Old Town Ale House. 219 W. North Avenue, Chicago.

Richard's Bar at 491 N. Milwaukee. Bring your sunglasses if you plan to stay here.

Working backwards, our third stop of the night was a place called Richard’s Bar at 491 N. Milwaukee.  An Italian themed dive, that is brightly lit and serves 75 cent hard-boiled eggs to their late night clientele.  In complete contrast to what 1s generally considered a standard criteria for most dive bars, Richard’s lighting choice is to keep the place fully lit at all times.  As a result, Richards was also the cleanest of the dives we attended, even though the air quality inside the bar was reminiscent of days long gone by.  Without giving too much away, let’s just say there is not a crowd located outside the front door of Richard’s like there is in most other drinking establishments in the great city of Chicago.

The easiest way to describe our second stop of the night is to flash back to another Chicago classic.  Just think Bob’s Country Bunker.  You know, that place were Jake and Elwood played both types of music, Country and Western.  The largest of the dives, it was already set up for the music later that night, and the only thing missing was the chicken wire around the stage.  It was sparsely populated when we got there, with just a few colorful after work locals to add some flair, but as we departed, the later crowd was starting to arrive.  The high light of Carol’s is the steel front door.  I am not sure if it was designed to keep people out, or to keep them in.

The steel door of Carol's Pub, located at 4659 N. Clark Street.

A real find, and a real Dive. Rose's Lounge at 2656 N. Lincoln.

Saving the best for last was not on the agenda for this trolley tour, because in my opinion, the best dive bar we were shown that night was our very first stop.  Almost invisibly located at 2656 N. Lincoln Avenue is the small doorway to Rose’s Lounge.  To start, it is a Lounge.  That alone should qualify it as a dive, but even better still is that passing through the red and white door is like taking a step back in time.  The wood paneling and couches are reminiscent of your grandmother’s living room, or a basement rec room circa 1972.  Rose has decorated her establishment with almost every knick knack she has ever gotten, and when a string of Christmas lights around the bar burns out, a new strand is added without ever taking down the old.  Rose herself is slow-moving, so order two drinks at a time.  And don’t expect a large variety.  Tap beer will be Miller Lite or Old Style, both at $2 a frosty mug, but odds are if you order the Miller you are still getting the Old Style anyway.

My favorite barkeeper of the night, Rose at Rose's Lounge.

The Chicago History Museum Pub Crawls have been a popular tour since 2007, and there is a tour to meet most people’s taste.  It is a lot to cram into a three-hour tour, but much like Gilligan himself, it is something you can get lost in.  If you find a stop along the way, you can always stay, or just take notes and return later.  I had never been to any of the stops before, and I will likely not return to half of them, but the chances are pretty good I will find my way back to Rose’s Lounge again.  There was so much to see, and just not enough time.

Anyone planning a trip there, make sure to give me a call!