Never lived in Bucktown, but this bar almost makes me wish I did- the perfect, respectable neighborhood bar, with good drinks, mature people, free live music that's often actually good, and smoke free. Not an everyday bar for me, but one I go to when I want some half-way civilized drinking around half-way civilized people...Like I said, not an everyday bar for me- the kind of place you might actually take your cool parents! read more

Surprisingly, The Charleston has yet to be squeezed out by the overdeveloped, overpriced, restaurant/bar/retail "scene" choking the neighborhood. What a trainwreck Wickerbuck has become...sad. ANYWAY, I love that Charleston is still just a real, old bar with old music from an old turntable under the bar. It's the real deal, not a a phoney, plastic spot "distressed" to look antique. My only dig is that they could get a bottle or two of some decent gin. read more

This is one of my favorite neighborhood bars in my hood. No frills, live music, games for the adventurous, and cheap drinks with friendly service. I need nothing else when looking for a low key evening. read more

I officially love this bar. On a Thursday night it was fairly quiet, rocking some hilariously nerdy music, and serving up great drinks. We had an awesome time and the bartender was incredibly sweet, giving out great pours. So yeah, I recommend it if you want a place to relax and talk to friends. read more

So I went here with coworker for the first time on a Wednesday. It was SO amazing! I was totally blown away by this place. It's so pretty. The bartender played the Twin Peaks soundtrack. It was straight amazing. Then, because I was so excited over this place, I took a friend there on the following Friday. THE WORST! What kind of terrible adult contemporary music were they choosing?! Why even? Maybe they want 40-50 somethings in there. I get it if that's the case, but I was just really confused. What a 180. Super disappointed. I'll just never go on a weekend I guess. Please keep playing Julee Cruise and I'll always bring you business! read more

This place was cool. I liked the chalkboard walls and powder room before the actual bathroom was a nice touch. I havent been there before So I cant comment on the owner switch. I think I had a good time bc my friend was the dj and we had a good group of ppl. Love the photobooth idea, but too bad after paying no pictures came out. What was suprr annoying was that the speakers kept going in and out. For 7 dollars a beer I expect A decent quality sounds system, at least one that stays on, I was to distracted by the in and out music to fully enjoy myself. I think its cool that they dont take cash. it weeds out ppl and brings back regulars. The atmosphere is a nice mix and they had lil sumpin sumpin on tap. Bttr sound system, and i just might return. Also ya the screaming get out, very annoying. read more

Cool neighborhood place. Seems to have some live music often as well. Drink prices are definitely right on track considering the good quality of them as well. Also, if you're a beer drinker, they've got plenty to choose from!!! read more

Great local pub with nice pool table and local jazz and blues bands. They are Chicago's first non-smoking bar I do believe. They host a great block party in the summer and a chili cook-off in the winter. Nice place to relax and chat without being smoked out. read more

I haven't been to the Charleston in a while but I've always had a good time here. They make a great Manhattan, by the way, best I've had. One night a long time ago I was there during what I assume was an open mike night yet it seemed even more casual than that. Anyway, one of the people who went up to perform was playing a trombone. How cool is that? When do you ever get to see a trombone player at an open mike? The old bar is quite beautiful and did I mention they make a great Manhattan? read more

I have only been here once & keep meaning to come back. It's a lovely place & it feels like home. It's a dive, yet still feels classy. Live music, nice ambiance where you can go somewhere to have a good conversation. read more

I'm not sure why people consider the Charleston a dive bar. It's got a old-school feel to it, but it's mostly filled with hipster yuppies (I can say that since I tend to fall in that category). It's not a trendy bar, but then again it's not like they have a lot of great beer specials that you'd expect at a dive. I think this place is transitioning to more and more yuppy, which is good or bad depending on what group you are in. Personally, I may be a yuppy but I appreciate good deals and that's just not something you're going to find here. The bands are good (though they make it very difficult to talk), and they do have a good selection of beers and wine. It does have a good ambiance, but I'm a budget snob. I'll come here when my friends want to, but it wouldn't be my choice. read more

I just moved back into the neighborhood and have no air conditioning. I moseyed over to Charleston one day after work when it was 90 degrees still at 6pm just planning on having a beer and cooling off before I made myself an ice bath at home. I returned a few weeks later for after dinner drinks to find a band playing a gypsy zydeco type sound, and again enjoyed my time there. A perfect spot that will suffice as a local stalwart and a weekend destination spot. read more

Besides the douche who refused to acknowledge our help to his finding his dropped money, this place is pretty good. They've got all the typical suspects in regards to beer but as a bonus free live music. The band at the time was folky/bluegrass and not too bad at all. The crowd seemed into it as well which helped the overall friendly vibe despite one of the fools we happened upon... read more

Super cheap. Cash only. Nice setting. Relaxed environment. Right off the block from where the bf lives. Good for a night cap or a quick drink to kill some time. read more

Met a friend here on a whim and fell in love. A definately beautiful atmosphere and the people were friendly and unpretentious. I actually got a very kind UChicago grad student to give me a impromptu physics lesson! That and a good glass of wine at a reasonable price as well as the awesome live music makes this a great getaway. read more

A nice, quiet little bar with some good bartenders and a B+ beer list.

Went there on a weeknight and present was a lively crowd of bucktown hipsters and cool kats.. Nice bartenders and staff. Someone was making a chalk mural in the back which was cool to watch. Drank a crazy whiskey and fruit based concoction that I wish I could remember the name.. really good. I like the nice dark wood of this cozy neighborhood spot. read more

Hands down my favorite bar in Chicago. A great atmosphere and crowd. A great selection of drinks and service by John Smillie behind the bar! read more

this place is certainly not a dive considering the price. The crowd is interesting to watch though

Go early to see Scott on Saturdays. He makes great drinks!! Everybody loves Scott. He's a great bartender.

Yes! Cheap beer, good live music (and I don't usually feel that way), great bartenders, fun contests, boggle, great crowd. Yes!

Scott, the owner, could be the most normal and friendly bar owner I have ever met. I've heard about the service being not so friendly but I didn't have a problem with the two ladies behind the bar and the live music was the final kicker for my 5 star review. read more

Me Like. 4pm, a couple of old locals sitting at the bar....and old Beatles records playing while a black cat walks across the bar. Me Like. Crowd kinda changes on fri/sat nites....obviously, but overall.....this is my kinda place. There aren't 74 flat screen tv's to kill conversation (not to mention more brain cells than are already being killed by the whiskey sour)......the staff usually have pretty great taste in the records they play....and when they have live music, it's usually pretty interesting. Or, you can grab battleship out of the closet and crush your feeble friends in naval warfare. It's my kinda bar. It's also 2 blocks from home, so yeah....it's my kinda bar. read more

This is a pretty good place overall. The tables having stools is a minus since sitting for long periods can be not comfortable. Beer list was good(not great). The place is roomy and looks like it would be good to for live music. read more

I didn't have a great time here - but my girlfriend lost her ID here 2 weeks ago and they hung on to it. Saved a trip to the DMV a few days before flying home for thanksgiving. The lunch crowd was having a great time and I'll be back for a drink for sure! read more

Love this neighborhood bar. It's low key, comfy and has good cocktails. Late on weekend nights, it gets a little more lively with more people, music and they have a photo booth. read more

Nice ambiance, friendly staff. Beer selection was fairly limited, although they have some random imports from around the world.

I second all of the reviews that include "warm," "cozy," and "inviting." Yes indeed. And eclectic, affordable, and filled with friendly neighbors from any distance away into the bargain. I've seen just one band here, but I consider that enough to judge how thoroughly the Charleston makes its guest musicians at home. If I were to become a bar fly, I'd be one here and feel ever so content being so until I went to bar fly heaven. read more

I finally came in here the other night after passing by many a times and thinking "that looks cool I need to go in here." It was awesome to see that they have live music here a lot, which was cool although I wasn't digging the country band they had on Friday night. This place is super cool. They have books everywhere, games and a dart board. It was a super fun place to have a couple of drinks on Friday night. You should definitely check this place out! read more

My brother lives up the street, we went here for his and two other people's birthday shindig, and it was an awesome time. Cash only which is okay if you know ahead of time. read more

Great neighborhood bar. Awesome selection of beer and they make great manhattans too.

Relaxed, not crowded, neighborhood bar. Good place to drink with your friends or date, but probably not to meet people. And you know they are hip because they play vinyl. read more

Great place to grab a drink of any kind. Bartender was friendly and engaging. Price is right.

One of my fav spots in the hood. Best Manhattans around. Great djs and stellar photo booth. Perfect date spot, slip them a kiss in the photo booth FTW. read more

Great neighborhood bar! Excellent for meeting up with friends or having a date night. While considered by some to be kitsch, I find their cash only business to be a major drawback. read more

Great neighborhood bar! There is always some good live music. The space is small but pretty cozy and most nights of the week you can find a place to sit. The beer selection is pretty good and at decent prices. read more

The Charleston is a great place to take yourself seriously. If you are having trouble thinking you are the best, that everyone around you are Philistines, or that you know more about (insert nominal interst here) this place will give you the smug shot in the arm you need to get back on your high horse. It's fine. Nothing really to distinguish it from other similar bars. read more

me likey. drinking stiegl without smoke or irritating dudes about makes me feel like i'm in my living room.

Recently remodeled, now has the most uncomfortable seating ever. Church pew benches that would make a monk cry, lab stools with stainless stell seats, one table is actually a small bank safe with no place to put your legs. It's awful here. Stay home, drink alone, at least you'll have chair with a seat back. read more

Wow, first time on here as a member, prompted by reading all the reviews of this place. I have lived by the Charleston for years and it would have been a perfect, convenient little neighborhood bar for me but it never was. I would always try to give it another shot but every time I would go in there, I felt like I was shunned from the staff and regulars at the end of the bar. To get a drink, I would have to walk over to the other side, stand there with my empty glass, wait for bartender to finish whole conversation, get the stink eye, wait patiently for the conversation to end the second time before I get my drink and then walk back to my seat. No smile, no "how are you?", no recognition or any attempt of pleasantry what so ever. The beer was never anything special and cost a lot more than the bars down the street. The only drinks they served required no bar tending skills and god-forbid if you would try to order a 'fancy' martini. I would occasionally have to meet friends there to listen to live music, which was nice but so loud we would have to sit next to the entrance. My daughter went there and was snubbed by the staff as well when she went there with a friend. Then when I heard it went up for sale, although I was excited to see change of hands, I cannot say I was not a little disappointed to hear that it would be another sports bar. Now, fast-forward a few months later and I'm walking by this bar that looks nothing like a sports bar. No sign? intriguing, no goat? Even better! I walk in, smiling staff, happy people! Some wonderful live jazz playing (and at just the right level). I can't believe it! It's like the little neighborhood bar I wanted 10 years ago. I immediately call my daughter to come and join me and after some hemming and hawing she agreed. Boy, was she happy! We actually could have a nice conversation, drink some nice cocktails and beer (which went down in price), chat with the friendly bartenders. Also, they have wine. They even told us that 100% of the first year of profit go to cancer research. For real???? I have been back twice now and each time has been just as pleasant. The decor is beautiful, the bar is beautiful, the staff is friendly and the patrons seem happy too. My daughter is planning her birthday party there and I feel like it is an appropriate place for both young and old. One thing I hope they do change, the name! Maybe it's time to call it something different because there is no resemblance to what it once was. Rejoice! read more