UPchicago Bar Crawl: Old Town

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We are on a mission to perfect the art of the neighborhood bar crawl… and I’m not gonna lie, I think we may have accomplished our goal with this one. Good beer, good pub food, so-bad-it’s-good karaoke, and one member mysteriously disappearing mid-crawl? Yep, we’ve officially done it. Old Town is, quite possibly, the ideal neighborhood for a bar crawl. Sure, there are renowned comedy stages in the area like Second City and Zanies. But if you really want to laugh, try watching the UPchicago staff sing Stevie Nicks tunes at the last bar of the crawl circa 3am. Now THAT is comedy.

Old Town is one of the most historic neighborhoods in Chicago, having gone through many a transformation over the years. One thing that has remained throughout the changes, though, are the plethora of local watering holes… perfect for our purposes. One needn’t stumble more than a few yards before running into a welcoming bar where the taps are flowing. Our first stop? A pub that’s had its doors open since the ’60s, and is known for naked celebrity portraits on the walls. Here we go again…

Old Town Ale House — Taylor Wolfe
219 W. North Avenue

A vintage juke box, second hand furniture and that certain “bar funk” scent only associated with good times. What more could a dive bar connoisseur like myself ask for? How about raunchy drawings of partially nude political figures all over the walls? Yes please! This my friends, describes one of Chicago’s most notable hole-in-the-wall’s, Old Town Ale House.

Old Town Ale House is about as unpretentious as it gets, so unpretentious in fact, they don’t even accept plastic. Make sure to bring your cash money to ensure you don’t miss out on any of the booze filled fun sure to be had at this specific watering hole. The beer list is simple, as are the regulars that fill the bar daily. The staff is friendly and easy going and the drinks are fairly priced. They don’t serve food, but offer bar snacks instead. Do like we did and post up at a table with some good friends, good beer, and watch as the graphic wall art turns funnier with each drink you put down.

Wells on Wells — Erin Nederbo
1617 N. Wells Street

Wells on Wells was a fairly low-key bar, with two flat screens, plenty of tables and a proudly displayed Iowa Hawkeyes flag. On the night of our bar crawl, their special included 1/2 price appetizers. Naturally, this was excuse enough to indulge in some steak nachos, pretzel roll bites and cheese dip, and pita and spinach dip. All delicious and all very reasonably priced.

Also during our bar crawl, their draft pints, excluding Guinness, were $3.50. As it should be, with a name like Wells on Wells, their selection of beer on tap went beyond Old Style and Bud Light and including some Magic Hat and other options.The bar has a small patio in front as well as a sizable beer garden in the back that’s filled with canopied seating areas and benches. Downside: no Malort and a single stall ladies bathroom.

Declans Irish Pub — Gene Wagendorf III
1240 N. Wells Street

Declan’s, home to Old Town boozers and University of Oklahoma fans since 1972, was one of the friendlier bars on our Old Town crawl. Quiet on a weeknight, our group was able to grab a table and enjoy conversation without screaming into each others’ ears. The 140-year old mahogany bar was as gorgeous as advertised, and was backed by a solid selection of Irish whiskies, as well as a giant Gatorade cooler filled with vodka lemonade.

Looking back, I wish we had tried some of the food (I hear the fish & chips are great), but all I felt like ingesting at the time was whatever beer was on special and a couple shots of Jager. I blame Andrew.

Though I don’t feel moved to call Declan’s a destination bar, you could do far worse for a watering hole in the area. Beverages were decently priced and our server was prompt and had a good sense of humor, something that’s borderline requisite for dealing with this group of alcoholic rejects (read: the wonderful UPChicago staff).

Old Town Pub — Andrew Hertzberg
1339 N. Wells Street

Down the stairs and out of the rain we went, as we entered another speakeasyesque joint in Old Town. The Old Town Pub doesn’t have the crude, yet alluring paintings that Old Town Ale House does, but that’s not to say it doesn’t have a charm of its own. The underground lairish style feels classic, the wooden walls are welcoming and unpretentious. Likewise, there is a small little outdoor patio on Wells St., but was closed due to the inclimate weather of the evening.

Drinks were par for the course, but I was glad to find a Kronenbourg 1664 to pair with our Jameson shots (in lieu of an inexplicably absent Malort).  Since we had just eaten at Wells on Wells, we didn’t try any of the house specialty pizzas. As opposed to traditional Chicago style, the Pub does thin crust, covering most conventional toppings (Hawaiian, BBQ Chicken, Margherita, etc.), but what looks most interesting are the Mac & Cheese and Baked Potato pizzas. Might be worth a return visit to check those out.

The rains had attempted but failed to deter our bar crawl, but the near empty joint means they may have succeeded otherwise. That or the place is falling behind in a competitive neighborhood. That’s not to say the chill joint doesn’t have its place though. Our extended little group was able to sit at a table and all talk together, and lack of other patrons meant service was spot on. If only they had Malort…

Burton Place — Tessa McLean
1447 N. Wells Street

This small 4am dive bar is the perfect way to end an evening in Old Town. You’re to the point where the taste of your beverage doesn’t really matter, you just need a place to hang out, a friendly bartender, and maybe a spot to belt out some karaoke? While karaoke only happens on Tuesdays, every other night of the week this place is a great spot to check out no matter what time of the day.

The downstairs consists of one large rectangular bar where most patrons belly up. There’s a table or two up front and a darts board on the far wall. The place is generally very dark and has several old TVs hanging around the perimeter. For more space or simply a change of scenery, try the upstairs, which features pool tables and a party room. Music is supplied by a decent jukebox.

Grab some grub from their full menu of decent bar food or get your munchies on late night with some cheese fries. Like we did, as it was the last stop on the Old Town bar crawl. While Molly serenaded us with Stevie Nicks and Andrew stuffed his face, we said goodnight…at least until we realized we were missing a member of the crawl who I’ll choose not to name. A search ensued. Cheers, Burton Place. Thanks for the nightcap.

About UPchicago Team

Urban Philosophy is a way of thinking that you develop when you’re a true city person. Whether you’ve spent your whole life living in Manhattan, or you just moved from small-town Iowa to the city of Chicago, the longer you stay, the more you come to understand what it means to live in a city. Our Urban Philosophy is that no matter who you are, where you are from, and what your likes and dislikes may be, there’s something for everyone in city life.

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