I'll be making a trip out to chicago in a few weeks and am in desperate need of some local bar recommendations. Past few trips we've just wandered around north of the loop or wicker park, and we've always found places to drink, but I always get the feeling those 'great bars' are just around the corner.
My idea of a great place? It's the type of place where you can sit at the bar and get a decently made cocktail, a solid pour of whiskey, or at least couple local tap beers. The type of place with a bit of..character.
It'd be ideal if a couple bars were within walking distance of each other. I'd love to be able to make a night of it. But that might be wishful thinking.
I'll be staying in River North - so any neighborhood within a $10-15 taxi is on the table.
I like Pippin - right by the Peninsula Hotel. Kind of a charming, hole-in-a-wall bar oddly located in the premium part of Chicago. Friendly, cheap, with good bartenders. Can't beat that.
I'm more of a beer guy, so here's a website that I find useful sometimes, just plug in your city or address, it's pretty reliable.
Otherwise, I would recommend you head to the Clark St Ale House, great beer selection including lots of local brews, and a good crowd. Sort of irish pub feel. Across the street is Zed 451, which is the exact opposite, very contemporary, and has good cocktails and wine. There are a few others in that block that are worth going to, so if you hit that block you'll be good.
You can also probably walk to the bar in the Sax hotel, excellent bar (a little pricey), and there are many other good bars in that 3 block area that you can stagger to; some local bars, and some piano/blues bars. Zoom in on the google map around the Sax hotel and there are quite a few just north of it.
If you're willing to take the car ride, it's awesome. No food, but really great beer list. If you go on Sunday around lunchtime, they provide free bbq, (check to see if they still do).
If you're really willing to take a car ride, I would also recommend Hopleaf. It's much further north, but I can spend an evening there and be a happy man. Awesome food, including mussels, and a ridiculous beer list.
The Map Room is about four miles northwest of River North. A cab ride wouldn't be ridiculously expensive. By public transit, you would need to take a bus or el north and transfer to the #73 bus.
Hop Leaf is in Andersonville, six miles north of River North. You can catch the #22 Clark Street CTA bus on Dearborn and take it all the way there, although it's somewhat slow.