Went to Second Story Bar 5/5/23. Waited about 10 minutes for bartender to notice me. He was flirting with another customer. I get it, when you have someone paying attention to you, you can lose track of what you should be doing. When he did come over to me, he was making drinks for a group who arrived after me, again no problem, I get it, he looked up at me and I ordered. He delivered the drinks to the group and came back to make more drinks for customers who Just came in. As he was making their drinks he asked me can you tell me again what you ordered. He did start to make my drink and I forgot if I had asked him just to coat the glass with vermouth and throw it out before adding the vodka. He had the glass in front of me with ice and vermouth in it so I said excuse me can you throw the vermouth in the glass out. The response I got was "don't tell me how to do my job I know how to make drinks." It's called a service industry for a reason and I can excuse a lot especially when a bar is crowded but to get a response like the one I got is not acceptable. I am paying for a drink and I just wanted to make sure it was made the way I like it. It seems to me we have forgotten about customer service and simple respect when paying for a service. Needless to say I will not be going back to Second Story Bar. read more

The bartenders make this place work. The environment here is better than when I go up north. It feels less catty and more relaxed.

Well hidden. Found this place on chance to get out of the rain. The entrance is deceptive/looks residential. The bar itself has a very chill/friendly neighborhood vibe, rare for the neighborhood. The drinks were STRONG, delicious, and cheap. 10/10. read more

Great ambiance! Smaller gay bar in the heart of downtown. Friendly folks and great drinks! Definitely go if you're downtown

Small but call it cozy. It's always a great vibe and the drinks a good. Clean bathrooms and good music

Didn't realize it was a gay bar, came in for a shot (bar hopping) and it was a hefty size shot! Love how it's very lowkey but welcoming.

After reading the other reviews it makes sense for the type of service we received. We ordered drinks and then had to run to the bathroom, he continued to say that we couldn't have two to a bathroom and said it said that on the door when it doesn't...so we explained that to him that they need to put up a sign. Even before I explained myself he threatened if we did it again we would have to leave and it would be our "last drink". After I looked again turns out it was only shown on one bathroom stall which we didn't use. I want to feel welcomed but this was not the spot. The bartender was very rude and had so much attitude for what?? I would not recommend for girls to come because it really seemed like they favored the guys while were there. read more

"Are you guys looking for a gay bar?" How did they know!? This quirky second story gay bar's street signage isn't obvious, so the bouncer noticing our lost-ness called out to us walking by and invited us in. It was perfect. This place is a gay little Chicago gem for sure. I stopped by with a couple of my buds on a recent trip and we had a blast. First of all, the vibes are chill, but the music was bumpin'. N'sync played, and so did 2 Pac... that's my kinda spot. They also had Miller Lite, who needs anything else in life? It's upstairs, so I don't think it is handicap accessible- which is something to note. It's also really small and neighborhood like, not at all a club. If you're looking for a cute, fun, simple hang with some fun friends- this is your spot. read more

Have your Covid-19 VRC, on your phone or a copy in hand for admittance & for a good time. Enjoy!

Wednesday evening. Bored, and nothing to do. So I went back to the Second Story for the first time in a few months. Parked in front, walked up the steep stairs to the second floor as someone was coming down. Had to wait for them to pass; the stairs aren't wide enough for two people. They passed, and I continued up the stairs. Enter Second Story. Carlos, one of the best bartenders (and one of the cutest) was behind the bar. Now I KNOW I'm going to get wasted. He pours with a heavy hand and will not hesitate to give you a shot or...whatever. The clientele hadn't changed much since I've been there last...your typical guys there to have a good time, your overserved patrons (more on that in a moment), and then those individuals, like me, just there to chill out, have a drink and some conversation. Usually they don't have any issues there and most people know when to cut themselves off....HOWEVER, the last time I was there a certain individual was there "from St. Louis" (aka Uptown) decided he wanted to continue to put his hands on me and get in my face. Bad idea. It didn't end very well for said individual. I ended up buying a round of beer to some complete strangers...having conversation...and making new friends. I'll be back, soon. read more

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

Loved the vibe . Great drinks . And amazing music ! I've never heard burlesque in any bar , this was the first to do so ! Also ! They are cash based so remember to get cash before going read more

Total dive bar....but I really did have fun here...=) Went on a random date with some guy since I was in town....and it turned out quite well....think I was a bit overdressed but hey I just came from a wedding haha... Anyhoo...the people were quite friendly....great ambience...great evening overall.....thanks for making my Chicago Vacation a memorable one! read more

Very small and unobtrusive, I've walked past this place on Michigan Avenue for years and never knew it existed. A tiny spot - maybe 10 bar stools around the bar and a few more along the back counter is all the room you have here, and don't even think about sitting (or even looking) at the ice machine - so the sign says. Second Story definitely isn't the biggest, the best, or even the newest, but I'll be swinging by the next time I need to mingle with my own while shopping the day away on Chicago's Magnificent Mile. read more

There are only 3 reasons why someone is lucky enough to find themselves in this AWESOME bar: 1. You finish up work somewhere in the loop and your straight coworkers have convinced you to have a couple drinks after a long day. That turned into a few more drinks...and dinner. Now the group is sauced and someone says "We should go to a gay bar!" (in an effort to make you feel more comfortable...sweet gesture). You usher them into Second Story Bar, one of them gets groped by someone (but pretends to not like it). Then a second straight coworker (now drunk) gets oddly jealous because no one has hit on him. You have a couple more shots and HOPEFULLY end up at home without too much of a hangover in the office the next day. 2. You finish up work somewhere in the loop, your wife calls you and starts yelling at you about the chores you didn't do, your kid's dance recital you missed, and the long time it's been since the two of you spent time alone. You start reminiscing of a past carefree time in your life where you had no responsibilities, no kids, and freedom to (ahem.....) EXPLORE YOUR INNER GAY SELF without any regrets! So...instead of being a responsible husband and father you ask yelp where the nearest gay bar is, find out that Second story is 1) very secluded 2) very dark and 3) has NO windows. PERFECT! So you walk in, end up groping this freakishly hot guy that's hitting on you, end up back at his place where he then asks you to PAY UP (his flattery wasn't because you're cute, buddy...duh). And you run home just in time to make the 10 o'clock news. 3. The person you met on a dating app has asked you to meet up for drinks one night. You're not sure if the guy is going to end up being MR. Right or Mr. "Oh hell nawl....never" so you pick this place because its 1) very secluded, 2) very dark and 3) has NO windows :) :) OK...that was a longwinded way of saying this bar is actually really fun! The music is always on point and the bartenders are always extremely nice. I love this bar...even though I've just accepted that I will ALWAYS run into someone from the 3 scenarios I mentioned earlier. ENJOY! read more

A friend took me to this place for the first time last week. Walking upstairs seemed so seedy, but inside wasn't too bad. I kind of felt like I was on one of those small-town coming out documentaries on Logo. It's a really tiny bar, but for the most part was fun for what it is. The demographic here was sort of older, but mostly I-just-left-my-office-in-the-loop-so-now-I'm-here-drinking-in-my-suit type guys. Meow. There are two bathrooms in the back with, clutch your pearls ladies, "only one person at a time" signs. I wonder what that's supposed to mean. Adjacently, there is a smaller back area by the bathroom as well, but I would have called that the closet. I ordered a couple sweet tea vodkas/lemonades and they were stronger than what I was used to. Needless to say, I was a little bit of mess the next morning. The bartender there took some time to get our drinks but he wasn't stand-off'ish. And if a hooker ever had famous last words about this place, it would be "cash only". read more

I have no idea why I did not give the full 5 out of 5 stars for my initial review of this place. Kind of a tragedy. Love the music. Love the strongggg drinks. Love the sassy bartender. Love the size and intimacy. I. Love. Everything! read more

Visiting from SF and came across this cozy bar. The drinks were amazing, great diverse crowd (ages and ethnicities) and the bartender/DJ was hilarious, charming and welcoming. Would definitely come back. read more

I've heard about Second Story from numerous people. After seeing a movie at the AMC up the block, and not ready to go home. I found the courage to go into the bar. It's a small bar, to begin with, but very inviting. I was there on a Saturday night. The bar is cash only! So hit up the ATM before you go. I don't remember seeing one inside. While the place is small, it was very diverse, and everyone was chatting with each other and having a great time. I've been in other Bars that seem more click'ish. The patrons were young, old, gay, straight, Out of towners, locals, regulars, and a few people you've probably seen on a dating app and wanted to talk to or have. The staff was awesome and attentive to everyone. Music was good and didn't kill the vibe or your buzz. If I ever wanted to be a regular at a place it would be Second Story. It's five stars for a great first experience, but I'll go back a few more times to see if that rating holds up. read more

I could not believe the bartender that was on duty July 24, 2023. I was with a group of friends who I took to the bar since in the past, I had a good time there. Our bill was getting high and some of our group was getting ready to leave. In order to pay the balance before some of group left, we asked for the bill. We paid the current balance of the bill (We were not "cashing out."). The bartender went up to one of the group and was visibly angry because he was upset with the tip he thought he was given. He said to one friend that , "I know you have more money than this." From then on he refused to serve those of us that were planning to stay longer. He proceeded to intentionally ignore us and would go to others who put their drink orders in after us. We were not leaving and was planning to tip the bartender appropriately upon our departure. Having worked in the service industry, I know the importance of tipping. If I did this when I was working in the service industry, I WOULD HAVE BEEN FIRED ON THE SPOT! read more

A hidden gem with an intimate interior that if you're not paying attention you'll pass it up. The staff is quick to serve and friendly. The patrons are friendly as well. We met a couple while sitting at the bar who gave us some pointers and recommendations during our time in the city. read more

I used to go to this place when i worked near by. Zack has been serving me libations forever! A nice dive gay bar to check out. Can't go wrong! read more

Was okay. Strong drinks which I appreciate. So cold and loud though. I was told people were super friendly and gregarious but when I went that wasn't the case. Everyone was in their own little worlds. 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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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

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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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

I never had been so turn off in my entire life! My encounter with a person here made me want to turn straight. I almost asked my friend, "Do you want to date me?" After volunteering for Diversity MBA, Chelsey and I decided that it was time for beer. I suggested Second Story Bar. I saw this a week prior, and it was suggested by a new acquaintance. However, we wanted to know the specials. So I gave them a ring: Me: Hi, do you guys have any specials today (Friday)? Gay guy on the phone: Hon-eee....everything here is special. Me: No....really?! Gay guy on the phone: Either you come in or not? (click) :O :O :O I am horrified. I didn't have a chance to get the person's name. Me: Chelsey f! this place. Let's go the dive bard down the road. Chelsey: What happened? Me: (tells her the story) Chelsey: God, really? Jesus. Me: Yea, sometimes I wonder why I am gay. And this is one of many people I have to deal with. *rolls eyes* Some gay guys are worse than pregnant women with morning sickness!!!! Let's stick to straight bars. read more

Because I am a straight woman, I try not to go to gay bars anymore unless I am invited by an LGBTQ friend. I don't want to invade someone else's safe space, and I have seen Trixie straight girls take over gay bars for bachelorette parties, etc. I don't want to be that woman. But Zach, one of the bartenders, is an old friend of mine who of course welcomed me. All I have to tell him is, "I want something sweet and strong with _____," and he whips up something delicious. He works Monday, Wednesday and Friday until 8, by the way. There is definitely a daddy bar vibe there, but everyone I have sat next to has been super nice to me. Plus, the bar is convenient to buses and the el. Great place to go for a drink after work (or shopping on the Mag Mile). Bring cash and tip Zach well. He's awesome. read more

I'm not gay, but god do I love this bar. Everything about this place is hysterical. Its a filthy dive, yet its steps away from the glamourous magnificent mile. Surrounding bars give you tiny watered down drinks at obnoxious prices, but Second Story serves up real stiffies (pun intended) in huge glasses for a fraction of the price. And to top it all off, being a guy I get great service here and frequently get offered free shots by the bartenders. Bringing girls here on a date is totally over the top cocky too. If you don't immediately understand why that is, you probably never will so don't waste your time parsing that statement. Oh and I love the sign on the bathroom doors that reads "Only one person at a time!" Its a tad difficult to find the first time you go, so just keep your eyes pealed for a bunch of gay guys hanging on the sidewalk smoking cigs in front of an innocent looking stairwell with no signage. read more

Against my better judgement I decided to give this bar a second chance after we determined it was likely the person I was with was drugged by one of the bartenders several years ago. It was a terrible decision to make. I have never been treated so poorly at any place of business. Not only is the bartender, Carlos, a drunk, but he openly insults guest that he finds imperfect in his eyes. After suffering a direct insult about my appearance and the beer I was ordering, I was denied service for what was a mixute of both apparent imperfections. When I talked to the manager the next morning I was told that I must have misunderstood him, which quickly turned into me being told "i can't take a joke". It is apparent that this establishment, its staff, and its manager have zero respect for those that are not their own. Since this time, it has become apparent to me that most of their patrons find it acceptable for a bartender to be obliterated, treat guest the way I was treated, say they don't remember because we're drunk, and move on with life. This leads me to an unfortunate assumption that their patrons are, indeed, just as terrible as the Carlos and his manager. read more

This was a great find; only 75 steps from Michigan avenue as their matchbooks point out. You ascend a somewhat dark, smelly set of stairs and find a true hole in the wall above an Armenian restaurant and below an astrologer. The crowd was a mix of people from 25 to 50. I ordered three gin and tonics and paid only $16 which is weird because that comes out to be $5.33 per drink. That's dirt cheap for this area where we paid $27 for a similar round at the last area bar we were at. It's a small bar, but we were able to find seats on a Saturday night. I didn't care for the music, but if you like Fergie you're in business. read more

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

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

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

This bar smashed any preconceived notions that I had about nightlife in the Loop. It was almost like walking into an alternate universe. Literally just a hop off of the mag mile, Second Story is a bar that looks like someone just converted an apartment into a bar. It's cozy for sure, but everyone is super friendly (and not too grabby!). Prices are very good, drinks are strong, and there isn't a pretentious person around. I wish they had a better beer selection beyond the standard domestic piss/corona, but the liquor selection is solid. As a bonus, you can walk up one flight of stairs and have your fortune told! Cash only, but there are plentiful Bank of America and Chase ATMs nearby, so it shouldn't be a problem. read more

Most importantly, at Second Story Bar the drinks are cheap and strong. My bartender was practically giggling as he poured whiskey in my glass for what felt like hours. I'd pay double what I paid for a drink that strong at my favorite bar (Scarlet LOL). The place is a total dive, and I love the down and dirty vibe. It's small, dark, and mostly filled with older guys. Lots of stares, but no glares +++ The location is convenient, as it's close to my 9-5 AND the Levi's store - wow!!! I'd recommend this dive to anyone. You and me together, 4 STARS 4-EVER. read more

This is a gay bar(I didn't notice signs of that on yelp plus there were about 4 women in there). That being said the other patrons were really friendly as was the bartender/owner AJ. This place has a lot of bad reviews cause of a former bartender named Carlos but he's gone so no worries. I mentioned that I walked in to that place to a gay friend of mine and apparently it's the oldest gay bar in the loop so I guess there's that. One of the very nice gentlemen was explaining that the back room was mostly a orgy back in the day and it still could be if I was interested. I respectfully declined but BS'd with everyone, had 2 drinks, and continued on my solo bar hop back to my hotel. It was fun and the experience was pretty funny to me. read more

Second Story Bar - Wow, this bar surprised me in a lot of ways... - Gay Bars Near Me - Chicago, Illinois

Dude.... The drinks are dirt cheap, I mean trailer park cheap. If you can deal with some older gentlemen who are just having fun it is a great after work/get the party start place. No F-ing joke: $4.50 for a 7 & 7 tell me any other downtown bar that has that? Side note: Please avoid the back bathroom on Friday there is this giant weirdo who pees with the door unlocked so people walk in on him, other then that you are golden. Ooooh, the music kicks ass for old school lovers, can you Donna Summer? read more

I haven't been to this place in well over 10+ years. Very small and quaint. Great place to stop to get a drink after work before heading home. Going on a Tuesday, there were a decent crowd before 10p. With it being a school night and before 11p, I am quite sure it might not get that crowded but who knows. If in the area, definitely worth a stop by. read more

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