the best pic I could find online

1935 W. Chicago Avenue

(312) 243-5600

Cleo’s is the bar you pick when you don’t care too deeply about first impressions. When I think of the bar (with grilled food, more on that later) the dim lighting comes to mind. Not dim in a defrocked Ricardo Montalban type of way, but in a “a bunch of wet kindergartenders on a field trip just sullied our tile floors” kind of way. When one walks by from the south there is always a jetblack maned underfed youngster (grandma!) acting as de facto greeter, perched on his seat, blowing smoke within a 15 degree radius of my sad self. The bouncer, usually a mere 20 lbs. heavier than myself usually seems grateful for the additional company.

Lighting, as we all know, is key, and Cleo’s scores several datingdish points (tada!) by stringing little red lanterns in the front room. If you can squeeze in a seat among the 30 and 40 something hipsters and other somewhat questionable types you have scored. Otherwise you are relegated to the Siberia of the back room, which has the dull warm flourescence that makes you question your eyesight. In addition the Olde Chicago favourite, the sports monitors/monsters become a hindrance to that first, second or frankly any date. I had to compete with my date who had roving eyes there, not for the dishy waitress, but for ESPN2 tennis.

The drinks are relatively affordable, though I remember the at best average wine costing a bit more (was it $7?) which I think is ridiculous considering the ambiance and House vintage. The service, usually in faux vintage t-shirts, is palatably friendly but again, curiously absent at that moment you’re desperate to pay and get away from that awkward date, which would be an unremarkable experience at Cleo’s.

The summer provides better opportunities for dating there, because the beer garden is open and there is a more expansive provision of saxy lighting. Unfortunately one is forced to sit on that awful metal chair that leaves a diamond pattern on one’s tush. Additionally I had the experience there with my dear friend L (not a date but who cares) of having to GET UP and get my own water from the near empty cooler. And pay for table service on top of that. Quite the offense. Though I shy away from food reviews, Cleo’s is NOT a place to dig into anythng healthy or colored anything other than brown. It’s fine if you want the conventional bar food trappings, but even in that case, it’s just OK.

In summary, Cleo’s is ideal for the after party party with that date you already know somewhat, when you’ve been swanked out by the loungy, throttling beats of the clubs with low furniture. (Why is it clubs now have such low furniture? Seems like a liability, even without imbibing martinis ) The relatively lower price point will come as a relief, the softer music will soothe your tinnitis strained ears, and the nonambiance will neither intimidate nor enthrall you.

In other words, it’s just ok, but awful if in the back room.

Cleo's in Chicago