I LOVE Second Story. This place is basically a much smaller version of North End SMACK dab in the middle of the Magnificent Mile. I had heard of the legend of Second Story on many occasions (like the creepy cab driver telling us where to pick up in Chicago while we were on our way back from Halsted) and had to check it out. I was with friends in Chicago for Restaurant Week and dragged them there after dinner. They were sufficiently terrified and acted like they were way too good for the bar so that's why it's tops in my book! The reviewer who said this place is like your gay uncle's basement in St. Charles could not have been more spot on. From the obligatory disco ball to the frosted mirrors this place could not be any more out of 1980 if it tried! There's also security cameras trained on certain areas of the bar (like the creepy staircase you have to climb to get up there) that make the place two parts creepy and one part awesome. Also props for the music videos they were playing that were even better than you would normally find at Sidetracks and Roscoes. Let me make it completely clear....this is NOT ROSCOES OR SIDETRACKS. If you want sterilized bars with roving barbacks with earpieces like they're Secret Service agents this is not the bar for you. If you want a laid back place with cute bartenders and great drinks go to Second Story! I will be back anytime I'm on the Mile! read more

I have been coming to this bar ever since I moved to Chicago, 4 years ago. I have to admit, I love this place. It is a great bar to come to for after work cocktails, great place to hang out on a weekend night with friends...pretty much a fun place any night of the week! Cheers to Carlos! One of the best bartenders in all of Chicago! Not only does he have a smile for everyone, he is attentive, plays the best music around and makes fantastic drinks! The drinks are very strong and cheap, big difference compared to boystown bars. The people that come here are young, old, laid back, no attitude. I hope this bar is still in business for years to come! It really is one of Chicago's hidden little gems. read more

Cool place to chill close to my hotel smelled a little funny but other then that chill read more

Second Story Bar - Visiting!!... greetings from Houston, Texas - Gay Bars Near Me - Chicago, Illinois

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Woah, what happened to this place? I used to come here a lot, but have since moved away. Decided to revisit for some casual drinks while in town. Bartenders were not friendly at all, and one seemed to be blazing drunk. Killed the music 4 times in succession to scream "who wants a shot?" To no response, again cuz I think he was drunk. He kept killing the music and screaming it until a bunch of people raised their hands. At which point he started singling out those in the bar with their hands raised, insulting them, and saying "ew, but not you bitch." On top of that, my bf had his fresh drink spilled 5 seconds after ordering, we were given a filthy soaked rag to clean it up ourselves, and then charged for the replacement drink even after an original generous tip. So you can insult customers, offer shots to an entire bar for free, but not replace a full drink spilled by accident? ...gotcha, but I'll go elsewhere. Really a shame, this used to be a very fun, friendly, chill place to go. read more

This bar is not really secret, but its often overlooked. I'm sure you've walked past it many times on the way to The Gap. This is a super fun and friendly place to watch old school videos or old school movies like Mermaids. Although sometimes they just have regular tv on. Its like your buddy decided to make a bar out of his living room. We pop in after we've seen some theater. Its usually a pop-in but don't stay all night kind of place. The patrons are very friendly and fun, and you can watch people leave on the stairs cam! That's extra entertaining later in the night if the person leaving has maybe had one too many. Sometimes they'll serve free pizza too. The drinks are cheap and its cash only. I'm removing one star only because sometimes they need to pay a little more attention to the ladies' room. It can be iffy in there! read more

Typical gay bar. Great location! Very dark inside and bartender was a smart ass. I attended with a gay couple, and the other 4 of us are straight. Did not feel uncomfortable at all, so don't worry about that at all! It was packed due to st Patrick's day so we were left in a back room that was pretty much a storage area. read more

I'm a fan of dive bars, and this is a hidden gem of a dive bar. My friend and I tried this place out after work one fateful night, and almost walked passed it - it's very nondescript from the outside. We trudged up a narrow flight of stairs and found the smallest bar I've probably ever been to - it's the size of one room. We had some good stiff drinks and had a good time. The clientele does skew older, but hey it's a dive bar! And it'd downtown, go to boystown if you want twinks. The only thing I'd change is that the music was blaring so loud that my friend and I had to yell to hear each other. I'd definitely go back! read more

Really enjoyed this bar. Cash only so my longevity was dashed quickly. Got some easter candy and was offered popcorn. Good shit. Sunday bartender is super nice and charged my phone. Btw they are partial to airing Golden Girls. Amen. read more

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Awesome place for drinks. Never too crowded with it's own dedicated regulars, most tourists and out-of-towners completely overlook this place. I prefer it that way, it's a good hideaway spot to enjoy drinks with friends after work or before/after any even near downtown. Drinks are strong, bartenders friendly, crowd is nice, music is good. Couldn't ask for anything more. read more

Bartender was super nice and drinks were reasonably priced for its location. Drinks were also STRONG. I'd say this is a hidden gem, would recommend for a quick drink. read more

After a very long day of work downtown, I decided to stop in at Second Story. It was my virgin voyage there and all I can say is, I will be back! I had a craving for a Margarita and Second Story did not disappoint! Very nicely mixed, flavorful drink and I got the majority of my $20 bill back in change. VERY reasonably priced! Now a little about Second Story from a newbie perspective. It's small! It's cozy! It's fun. You might be a stranger when you walk in but if you are the least bit friendly and personable, you won't be a stranger when you leave. If you're looking for the "Boystown bling", you'll be sorely disappointed. For me, that was part of the attraction! There isn't one pretentious person or vibe to be found at SSB. While I was there, I did see a couple of women stop in for a drink but they didn't stay too long. While women are certainly welcome, I think it's fair to say, SSB caters to a gay/bi sexual man crowd. Did I say it was small? The entire bar is about the size of a very large living room. I thought it was cozy and the type of environment that makes chatting and getting to know someone very easy. The "regulars" were very approachable and often initiated conversation. It was a very friendly place. I would also say SSB leans toward the "older" crowd. During my initial visit there were times I felt "young" and any place that can do that for me gets at least one star, just for that! I'll be back. It's a great little spot, right off the Magnificent Mile yet in its own little world there on east Ohio. I loved it! read more

Omg this place was fun! Welcoming and the liquor TOP SHELF but affordable had a grand time and the BOYS loved me ladies get yo life if a gay man says you're FAB you most certainly are! Baby Got Good Bar read more

We got stuck in chicago after a blizzard came through and came across this bar on our way back to the hotel. What a hidden gem! Everyone is so nice. Plus the bar tender played Jimmy Fallon skits on TV all night and gave us chips, candy hearts, and stickers for valentines day. Definitely coming back next time I come to chicago. Oh and come on, they have a disco ball! read more

Second Story Bar - Free candy hearts on valentines day :) So nice! - Gay Bars Near Me - Chicago, Illinois

Very 'quaint' gay bar with a few too many self-important queens for my taste... and that bug juice they were peddling as Maker's Mark--yuk! More reminiscent of rubbing alcohol than an Old Fashioned as it uncontrollably contorts the face into expressions of disgust, especially since the bar keep adds maraschino cherry juice instead of bitters. Still, if you want an $8.50 BASIC drink and enjoy getting 50¢ pieces for change at this cash-only bar, then go for it, gurl! read more

The funniest and best bar downtown! Carlos serves up some tasty fun delights for your oral pleasure! He always greets me with a smile everytime I come into the bar. I live out of town and sometimes years go by before I can get back there and he ALWAYS remembers me, what I drink and always makes me feels comfortable and taken care of!! Love this bar. And love me some Carlos!! read more

Second Story Bar - Carlos giving the love! - Gay Bars Near Me - Chicago, Illinois

This was a great bar to start off our trip to Chicago. I'm always down to check out a gay bar, but especially a gay dive bar! The drinks were cheap and the music was on point. They had a great Madonna compilation along with some new hits. I really like how they have a screen to show the music videos too. I was surprised how busy it was on a Sunday night. They have a great vibe here, and the disco ball adds a nice touch as well. Just make sure you have cash since they're cash only! read more

First word that comes to mind - random. Second word that comes to mind - fanfreakingtastic. Had some friends in town and they wanted to hit up some bars downtown where they were staying. I didn't expect I'd get to enjoy a gay bar in our downtown bar hopping. Random, but what a pleasant surprise! The entryway (a staircase to, wait for it, the second story of the building) was just begging to have a buff dude waiting at the top of the stairs requesting a password, like "black widow" or something equally clandestine. The bar is super small and super fun. Great music, with sexy videos playing, a row of stools overlooking the busy street below and gays galore. Me like. Very boy heavy, but aren't most gay bars (sigh). I said to my friend, I wish I could find a wonderfully divey little place like this that was full of lesbians. My search continues. The boys are friendly and chatty, which I love about our community. And the bartenders keep things bumpin' and fun. I will definitely be back. It's so tight in there you could go alone and no one would know the difference because the whole bar becomes a party of one. The drinks are big The crowd is friendly Cash only Small, but cozy Easy location if you are downtown shopping read more

The location of this bar is amazing and extremely convenient if you are a fan of downtown Chicago. Treat the bartender with respect and you will get nothing but good drinks and good times. It is small but that is part of what makes it easy to socialize with everyone! read more

Second Story Bar - Gay Bars Near Me - Chicago, Illinois

Wonder atmosphere covid compliant and the bartender was very cool and took care of patroons needs

Dive bar by admission....very interesting entrance where you feel like you are walking up an old carpeted staircase in an old Chicago apartment. The sign to have your IDs out seemed unnecessary since nobody was remotely looking at us when we came in. First thing you see is a bitchy sign to "stay off the f***ing icebox." Very divey in atmosphere: old, falling apart, cheap decor, these things can be quaint in the right setting. Very SMALL: about 50-60 people crammed into an area the size of my living room, nowhere to sit except in the back by the empty alcohol boxes on falling apart stools. Might try to come back at a less crowded time. Drinks were so strong they were hard to stomach and we all only drank half of them. I will try it again, dive charm and convenience to my downtown location make up for the size read more

This is a shout out to my after work pub, Second Story Bar. Yes, the old (and young) queens paw on everyone that walks in with a pulse and paw even more the ones that don't appear to have a pulse, but hey, we gotta be loved by somebody... And yes the drinks are strong and cheap and come with extras (Like all those paws). But everyone is sweet, respectful, and genuinely good people. You should be so lucky to be around so many gems. It's Chicago's best kept secret and if you don't like it, then go to boys town for whatever kind of over-priced, vacuous, and shoe polished plastic dummies you like to hang out with and be judged by all without so much as a hello or a casual foofie glance. On the other hand, If you would like to have a heated political debate with people who you will still love after bashing them for being so stupid, then this is your place. If you would like to have genuine comradery the way so many straight people get in much lesser places, then come to Second Story. As an honored recent addition to the regular patronage, we would love to have you. read more

Was looking for a local dive bar after getting tired of the overpriced, crowded place we had been at. We stumbled upon this bar and didn't realize it was a gay bar; not that being a gay bar would stop us anyway. We had a great time. The drinks were cheap and the people were friendly. read more

The Second Story Bar is perilously near my office, so I suppose it goes without saying that I have been drawn in by its beckoning neon on numerous occasions. It's rather like a gay Cheers. There are always regulars sitting around the bar. The atmosphere is friendly and the drinks are strong and cheap. Sure, it's a dive-y little place, but it continues to help take the edge off after a hectic day at the office. Thank goodness for that! read more

Odd Place! Small, cozy and friendly bar. It's the kind of place one goes to REALLY drink - but not the place to hang if you want 'eye candy'. The thing that struck me as odd was the bartender. I'm sure he was drunk or high or both. He wasn't unfriendly (when you could get his attention), he was just odd! The music was okay (2 TVs play with music videos); but Carlos would stop the song/video on a whim because he wanted to move on. It was just odd. It's not that I wouldn't go back - but there are better bars (including gay bars) close by; and after trying this bar twice, I doubt I will go back. read more

ABSOLUTELY RUDE. I just got into Chicago and found what I thought would be a nice gay bar but as I walked in and tried to use the restroom (because I had just walked 20 blocks) two "bouncers" came out of the back from talking, demanded I show my ID (I'm well over 21) before I could take a piss. Then before saying anything else made sure I knew they were cash only. This was two seconds into trying to pee. No sort of welcome what so ever. If you're a woman don't bother coming here. Happy pride guys. read more

Came here Gay Pride weekend, perfect timing! Cheap drinks, friendly patrons, chill atmosphere. A cute place to stop by and grab a drink if you're in the area. I had my first Redd's Apple Ale here, so tasty! read more

Crowded, cozy and a great place to meet the man of your dreams if you can pry him away from the booze..... Not a bad place....Enjoy! read more

The manager was extremely rude to me and my friend as we were trying to figure which ATM was the nearest to get cash as they only take cash. Did not feel like coming back after that encounter. Will definitely not be coming back! read more

Maybe there's new guys, but I'll tell ya.... AJ, Brian and ESPECIALLY Zach are all amazing bartenders. Such a great vibe in that place. Be careful with Zach, I think he's clairvoyant. read more

Wow. Really wish I could say a single good thing about the only gay bar in my vicinity. Came here with my cute femme date tonight, literally the second I get to the entrance the door man was extremely rude and says to me in an accusing way, "looks like you were really struggling on the way up the stairs" to which I kindly explained I am missing a leg. Then he proceeds to tell us we couldn't get in without any cash on hand (okay?) so we ran to the bank around the corner and come back within five minutes. We walk back up to the bar and a group of white people all arrive right before us. NO JOKE, this man LETS EVERYONE IN EXCEPT FOR US, then stops us and says the bar is at capacity. So in a matter of ten minutes this bouncer managed to be ableist, femme-phobic, and racist all at once. It's upsetting that we aren't even welcome at supposedly welcoming LGBTQ spaces. Don't waste your money here. read more

Cozy dive bar with the best music in town, and these yummy strawberry lemonade shots. $4 beers!

As mentioned in previous reviews, this place is highly unexpected, small, a bit of a fire hazard and low-key. Very low-key. The drinks are strong and cheap, and the bartender is nice. Went here around 11 on saturday, and it was pretty packed (around 20 people - indicating the size of the place). I would go again if I ever find myself in the loop. read more

Back again, this is just the hidden gym kind of place I love! Good drinks and the locals are always friendly. Unlike Dallas where we are all asses read more

Its a bar, a gay bar so you know its already fun as F! :) small, dingy but you seem to forget all that cuz once u walk in, everyone is laughing, enjoying their day, drinking, drunking and having a kick a$$ time. The service was amazing, the drinks were well worth the price and the music was awesome! Its is the gay cheers of indy void of pretensions so if you haven't been, go and enjoy! You will leave having made friends and feeling buzzed. read more

Been here last Sunday, that was my 1st time. Went to pick my friend from Union station but the train was late for hour. Bored opened my Yelp App, I found Second Story Bar and decided to go and pass some time. This Place is good, small, cozy and lil different. Weird thing is there are many pauses in between songs and the bartender keep spiking and put the songs mostly what he likes. HE SKIPPED MY FAV one too. Any way and yes ONLY CASH. I think I will go again :) For parking you have to keep looking around if you lucky i will get around as i got. read more

Not bad. Not fabulous. But it's a dive bar. If you're expecting this place to smell of roses and for minstrels to announce your arrival with a fanfare, then you are an idiot and deserve to smell the foot odor that permeates this place. I would have given the place 4 stars except the music selection was terrible. At one point I swear I heard Vanessa Williams. Seriously. This is supposed to be a bar, not a high school homecoming dance. Keep it peppy people! read more

The bar is small but cozy. They have a pretty strong regular crowd but also some tourists. Decent prices and all of the staff were nice. Try it out. read more

This is a perfect bar for me. Small, intimate, super friendly, cozy, cheap drinks, decent music. We loved it right away. We had originally just planned on stopping by for a before dinner drink, but dug it so much that we came back after our stupid dinner at Gilt Bar. We stayed the rest of the night and had several tequila shots. Bartender was super nice and cute. Also: it's cool to look out the bar window and down one floor. We will be back. read more

Rude employee as I walked in the door. Been there numerous times over the years but just walked out and will never be back. Hope you business is good cause there are lots of better bars in the Windy City! read more

Bad experience ... guy at the door was super rude to me and I felt like I was gettin racially profiled ...I'm Arab and queer and did not feel comfortable here. Don't waste your money read more