UPchicago Bar Crawl: River West

I love my neighborhood. It’s a small and often under-appreciated one. A pocket just over the river from River North and just East of the West Loop, concentrating around the intersection of Grand, Milwaukee, and Halsted. I get more confused faces when I say I live in River West than when I say I love Chicago winters. But the truth is, it’s one of the most accessible neighborhoods in Chicago. Within a matter of 10 minutes on any of the numerous public transportation routes right outside my door, I can be in Lincoln Park, Wicker Park, University Village, Streeterville or the Loop. Give me an extra five and I’ll make it to Logan Square, Pilsen or Boys Town. What’s not to love when you’re first love is exploring this amazing city?

And so after a diligent work meeting, the UPchicago crew decided to get out and explore the neighborhood we were in. River West hosts an eclectic mix of classic Chicago and the new and chic and both are included in our crawl. And when we were introduced to a new UPchicago mascot by the name of Walter, it was all downhill from there…

Red Canary- Jackie Berkery
695 N. Milwaukee

Billing itself as Chicago’s first “gastro-lounge,” you can expect all that goes along with the title. A swanky bar & restaurant with cushy booths and vaulted ceilings, this contemporary River West spot is a nice addition to the neighborhood.

The space is huge, with several rooms, an outdoor section, and a second floor with balconies overlooking the action below. Red accents every wall and furniture and vintage chandeliers are an elegant touch. The garden patio is a hidden oasis with 2,000 square feet of space for dining and cocktails. Vines cover the brick walls and trees shade wicker couches and tables perfect for lounging — definitely a good spot for a warm summer evening.

The drink list includes a decent craft beer selection, a comprehensive wine list, and several creative cocktails. The food menu is short, but satisfying. Try the pulled pork sliders or the roasted chicken with risotto for more conventional tastes, or fried frog legs and barbequed oysters for something a little different. This is also a good place to get a bunch of small plates and share. Service can be a little spotty, but a good creative cocktail can make it all worth it.

De Lux – David Frankel McLean
669 N. Milwaukee

To the unsuspecting this River West bar would seem rather average, which is why it’s downright delightful to see people’s eyes light up when tasting their food.

Delux has just the kind of bar food to cure a hangover. Smothered tots? Yep, they are as good as they sound. One pound of tator tots smothered in homemade cheese sauce, topped with bacon and scallions, and served with a side of homemade ranch. Did you catch all those “homemade” references? Delux shines with its variety of homemade sauces. The menu contains typical bar food done right, and they have great weekday specials including your favorites.

Their list of beer on tap is nothing extensive, but includes Goose Island Matilda, which I think everyone appreciates. They do have a pretty extensive list of bottles, which makes up for a short tap. Take your beer over to the pool table once you’ve chosen or dive into one of their deep comfy booths for TV gazing. In the summer they open a garage door of windows to expose half the place to the open air which creates a delightful breeze even if you’re sitting at the bar. And most of the locals (albeit everyone in this place is local) do sit at the bar. It’s just that sort of place with plenty of single patrons enjoying a beer and a burger before heading home.

Emmit’s Irish Pub – Dan Bush
495 N. Milwaukee

Every strange new country I’ve passed through, regardless of language barrier, has nestled in it a traditional Irish Pub. I’ve had a Guinness in KilKenny’s Pub in Ko Samui, Thailand, and thrown darts at O’Sullivan’s in Buenos Aires, Argentina. There is a recipe for the Irish pub that is contagious to the world. But for me, a Chicago native, Irish pubs are my comfort food.

Emmit’s Irish Pub could very well have been the model for these foreign establishments. On a weekday night the bar services a small older crowd made up of what I imagine to be local policemen and politicians. The walls are littered with Gaelic futbol jerseys and Chicago Fire Department flags, capturing the Irish-American blue collar history of Chicago (the bar is owned by two Chicago Fireman, Kevin Doherty and Ron Halvorsen ). Speaking of history, Emmit’s has quite the colored past. In the 1980’s, the bar was the site of 2 gunned down would-be robbers and Chicago’s abolition of the bar’s “dwarf tossing” (an old Australian pub tradition). What would a historic Chicago pub be without scandal?

Visit Emmit’s on a Friday night and you’d better sharpen your elbows and ruddy up your Irish nose, because the place gets packed with young folk. The juke box carries both traditional Irish music and modern fan favorites (see: Lou Bega’s ‘Mambo #5’). And if you are looking for an authentic Irish Pub for upcoming St. Patrick’s Day, Emmit’s will fill your glass with green beer and your ears with “The Wild Rover”.

Richards – Gene Wagendorf III
491 N. Milwaukee

Even abbreviated bar crawls are trouble. You’d think that by hitting fewer places you’d be inclined to end the night on a more sober plane. Not so. Doesn’t help when you pre-game, and it certainly doesn’t help when you wind up at a place as cool as Richard’s.

It’s a huge cliche to note that walking through the doors of a given establishment is like stepping into a time machine, but sometimes cliches are called for. There’s a reason they’re cliches, after all. Richard’s Bar is such a place. For what is essentially nothing more than a neighborhood taproom the crowd tended to be a little more on the dressed-up side. Having visited on a weeknight I’ll assume everyone had just gotten off work and needed to blow off some steam. You know, relax with good friends, good music, a cigarette and a beer. A cigarette? Yes. Although Chicago’s smoking ban has been keeping smokers shivering in the cold for a few years now, the occasional cigarette and cigar makes an appearance at Richard’s. The bar even stocks an impressive selection of smokes behind the counter, right next to the 75¢ hard-boiled eggs and the beef jerky. Old school. Really though, who could begrudge a man a puff on his stogy while soaking in the sweet sounds of Louis Prima?

Which brings me back to the music. I’m a bit of a dick when it comes to jukeboxes in bar. Much as I love to be able to get lit and punch up Musical Youth’s “Pass the Dutchie” at any given moment, internet jukeboxes make me cringe. A jukebox gives a bar character. The machine at Richard’s epitomizes this. For 5 bucks you can get yourself a full hour of Sinatra, Prima, Sam Cooke, Dean Martin< Otis Redding etc. As I was flipping through albums and punching numbers “That’s Amore” came on. Dan wandered over to say he’d thought about playing it but figured it would be too cheesy. I hadn’t played it either. Someone else had. Of course they had. And everyone enjoyed it. That’s the kind of place Richard’s is.

I have no complaints about this bar. The jerky was zesty. The drinks are cheap, definitely the kind of place you can lose yourself for a while and still have enough money not to piss your mugger off. Hell, something about this place made Peroni palatable. Or maybe that was the company. Hard to have a bad time with a crew that carries finger puppets around, you know, just in case.

Paramount Room – Tessa McLean
415 N. Milwaukee

You really can’t beat a $9 Kobe burger. It’s pretty much unheard of, but I’m not complaining. Paramount Room is one of those places you would probably miss if you didn’t know it was there, but it’s actually a rather large space with good food and drinks to match. In the building of a 100 year old speakeasy, there is lounge seating downstairs as well as more seating upstairs other than the main floor you walk into. With loft ceilings, low lighting, and lots of exposed brick and comfy booths, Paramount Room maintains a level of class without even bordering on pretentious or haughty.

And I’m serious about this $9 Kobe burger. Sure, add-ons may be extra, but most places wouldn’t serve you a kobe burger starting below $18. The poutine loaded on the pork and could have been a meal in itself, it was huge! They also offer better-than-average sandwiches and hand-dipped fish and chips. Their beer list is extensive, with the tap changing often and featuring unique local brews. Your server or bartender should be able to elaborate on the beers, and even tell you about some featured brews not on the regular menu. They also have a nice cocktail menu and I always appreciate a $5 beer and shot special. How can that ever be bad? Come for the food; stay for the drinks and the company at Paramount Room.



River West Bar Crawl in a larger map

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.


  • Olivia Stone
    March 4, 2011 | Permalink | Reply

    I can’t wait to visit my brother in Chicago so we can do this pub crawl! Sounds perfect for St. Patty’s Day. My first pub crawl ever was in London, and I had an amazing time. Just saw the trailer for the new indie film White Irish Drinkers, and I can’t wait to go see it at the Craic Fest. Highly recommend it for those who love good times in bars. http://bit.ly/eavzAE

    • Gene Wagendorf III Gene Wagendorf III
      March 20, 2011 | Permalink | Reply

      I was thinking of going to see that movie but then I ate dinner. Got too full to leave the house. Had a giant SPAM burger. I wouldn’t recommend eating a SPAM burger. SPAM is nothing but unsatisfying filler meat. And the people who work at SPAM, SPAMMERS if you will, are sad excuses for human beings. Fucking SPAMMERS. :)

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