In a neighborhood choc-a-bloc with some of most eccentric bars in the city, Cleo’s holds its own with its own funky “Heaven and Hell” motif, above-average pub grub and an intriguing array of specials that has the local bohemian crowd keep coming back. Though the service can be questionable at times, Cleo’s is a great spot for dinner, just a few pints or as the start to any Ukrainian Village adventure.

Not to be confused with “Cleo’s Three Fifteen” on the South Side (315 E. 61st St.), Cleo’s can be found on Chicago, just east of Damen. Though technically located at the northern edge of West Town, Cleo’s has that Ukie Village vibe, in the same manner of Empty Bottle, Sweet Alice, Inner Town Pub, and Rainbo Club, all of which are located within a few blocks. A humble black sign with white lettering hangs from the brick edifice of a two-and-a-half story building – note the halo over the letters and forked tail on the “S” – and is complimented by another Cleo’s sign in blue neon. Watch your step as you head through the double doors of paned glass and you’ll encounter the bouncer, one of whom I found to be an interesting chap. We came for food and, because Cleo’s is quite popular, the bouncer asked if we wanted a table but didn’t take our name. When asked about it, the response was: “I saw your ID, didn’t I? You’re ‘martini-shirt guy.’ I’ve done this for years.” True that.

Once inside, Cleo’s presents an assault on the senses. There’s a large Buddha mural just inside the door on the north wall, red-painted cement ceiling with red recessed lighting, and a funky multicolored mural that looks like a box of crayons exploded except for the faces. During my last visit, framed surrealist prints adorned the east wall but Cleo’s rotates the artwork on a regular basis to keep the bar “fresh.” As you try to regain your equilibrium, grab one of the large cocktail tables up front, if you can, in front of the large windows that open out onto Chicago Avenue in summer. To your right are a few more low-slung tables with glass-tops, animal print tablecloths and multi-colored candle holders, which lie in front of a large mirrored wall and under a pair of eclectic hanging lights.

A long wooden bar runs along the east wall and bows out at north end. Good luck finding an empty high-backed, black vinyl barstool there. Hell, just ordering a beverage can be a challenge, as you’ll have to wedge yourself in-between the regs and fight with the 1-2 stewardesses serving both front and back rooms. Behind the bar, you’ll find a dozen beers on tap and a few more in bottles, as well as a mirrored bar back with red string lights and various tchotchkes including a skull and hanging skeleton. The one-seater bathrooms lie opposite the bar, but are separated from it by a wooden partition with a colorful mural painted on it, and the jukebox, stocked with punkabilly, used to be found at the south end of the bar but has yielded to the digital version.

The entire front room is bathed in a netherworldy red and, considering both the staff and clientele, I wouldn’t be surprised if you find a forked tail or tongue in the front room… Make your way through the crowded bar area and you’ll find a more spacious, black & white-tiled backroom. You can grab a seat at one of the small tables placed in front of a black banquette the runs the length of the eastern wall, across from which is another colorful mural below thinly sliced rectangular windows. The kitchen lies through a set of worn, narrow wooden swinging doors set within the southern wall of exposed brick. Though the eastern wall and base of the western wall are painted dark blue (the Heavenly aspect of Cleo’s?), the small pool table is felted in red, matching the curtains hanging in the corners and above the inevitable Golden Tee machine. It’s probably come down by now, but I once spotted an American flag taped to the ceiling. A garden deck has also been added out back recently.

Considering that very few bars in the area serve food, Cleo’s stands out for its selection of appetizers, salads, burgers (including a pretty good veggie burger), sandwiches, surprisingly good gourmet pizza, and a few entrees including buffalo shrimp kabobs, barbeque salmon, and salmon pesto, all of which is illustrated on a laminated, four-page menu. Though I’ve never had it, many recommend the chili and the Sunday Louisiana Brunch is a hit with its eggs benedict, chicken & Portobello crepes, and French toast. Specials on food are offered through the week (not weekends) and, though they sometimes change from week to week, one thing is certain: a free appetizer buffet is offered from 11pm to 1am on Saturdays, and has become legendary. Mondays also feature 10¢ wings, and Thursdays bring $3.99 12″ pizzas. The service at Cleo’s has often been criticized, primarily because they seem perpetually short-staffed. If Cleo’s just had one more waitress working at any given time, it would be a great place to grab some pub grub. Until then, don’t be surprised if you have to wait a half hour or longer for your food, or for the waitress to come by for your drinks order but, on the other hand, everything at Cleo’s is dirt cheap especially with the daily specials, so if you want top notch service, head to a restaurant instead and be prepared to shell out a fair bit more for it.

  • “Cleo’s is the hangout of choice for twentysomethings who desperately want to be seen as artists even though they still get allowance and haven’t so much as broken a nail, ever. They migrate from the cradle of Michigan State University to the bohemian west side of Chicago because the ‘rents think that New York is too dangerous. After twenty minutes amongst the Christmas lights and micro-brews listening to the pre-recorded wicky-wicky sound of hard-labored house music, you begin to wonder why this place doesn’t take the plunge and just become an Irish pub. It’s neither hot nor cool and not particularly friendly. Aside from a pretty mean bowl of chili, it’s not really worth the trip to the middle of nowhere.”

    Shecky’s Bar, Club & Lounge Guide 2002

While I think Shecky’s has nailed the crowd (which I’ve found to be scruffy and unpretentious), I would argue that Cleo’s is most definitely worth a visit, even if it does seem like the middle of nowhere for those not living in the ‘hood. The joint has a more local feel during the week, whereas DJs take it upon themselves to keep the more loungey crowd grooving on weekends. Small jazz bands have been known to occasionally play at Cleo’s, but you’ll have to check with the bar as there is no set or advertised schedule at Cleo’s. For more information, check out the Cleo’s website. Until then, remember that the arsonist has oddly shaped feet.