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My Top 5 Favorite Chicago Bars

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“I’m a drinking expert.”

What is it about bars? I don’t know. The smell, the dark wood, the escape — I love it. I heard once that Chicago has more bars per capita than like anywhere or something and I liked that fact so I never checked to see if it was right. Either way, there’s a lot to choose from. Here are my top picks.

5. Bullhead Cantina – California and Division

Located around the corner from my old digs, this Humboldt Park gem shines like a pristine scratch ticket on a Wednesday afternoon. It’s got a friendly staff, whiskey-oriented bar, and the NO BULLSH!T special: a shot of whiskey, a tallboy, and a designer taco of your choice for $6. Try the grits & kale, it’s the best one on the menu. Cash only.

4. RichardsMilwaukee and Grand

This place is my El ticket to Happytown. It’s a classic Chicago dive. It’s got hilarious regulars who they should have casted for Chicago Fire. It’s got some fantastic art on the walls, the jukebox is solid, and for some reason you can still smoke cigarettes inside, which is pretty rock and roll. If memory serves, they’ve got a 14” tube TV you can catch the Sox on.

3. BeetleChicago and Maplewood

Big windows, open spaces, and high ceilings make this place a breathe-easy environment. It must encourage people meeting and having conversations, because I’ve had primo chats with random Uke Villagers. Family-friendly with a good kitchen and fully stocked bar with solid rotating specials. I even took the Viking Queen here on our first date.

2. Zebra LoungeState and Division

This piano bar is tucked between some of the wealthiest parts and some of the most brotastic bars in all of Chicago. It’s in the bottom of a month-to-month apartment building. It is a freak beacon. From Boogie hounds to friendly shemales, woolly parties, schizophrenics, sassy bartenders, bored trophy wives, and rabid investors. Celebrity appearances have included Bill Murray (tequila), Dave Chappelle (Heineken), and Jeremy Roenick (Bud Light). It’s where I cut my teeth. I call it Hogwarts.

1. Floyd’sArmitage and Oakley

Situated in a Schlitz Brewery-Tied House built in 1898, this Bucktown staple boasts the mantra, “Come for the food, stay and get drunk.” The food is certainly great (if there is a food special, get it). The bar is assuredly full (if there is a cocktail special, get it). Darts, killer soundtrack, and a great place to watch Cutler loft an interception. It’s where my cronies and I hatch our most dastardly schemes, and where I don’t remember leaving the most.

Honorable Mention: Wyler Road – Central Park and Belden

Creative combinations of booze and food served by beautiful tattooed people tucked away on a quiet corner of Logan Square. A nice back patio for when you and your friends want to melt into a cocktail. Bartenders know some good jokes as well. Would have made the list, but Wyler needs a few more reps to prove herself.