Second Story Bar

One of the best dive bars in the Mag Mile. I’m bias towards Bartenders Brian and Zach, but the everyone who works here are accommodating and friendly. Eclectic clientele. Sometimes, you just wanna go to a quaint bar, and, if you’re lucky, maybe get entertained with their loyal and sometimes “unusual” clientele. A MUST to come here. PS. It’s cash only, so please make sure you have cash on hand. Though they have an ATM in the bar, there’s a 7-Eleven and a Citibank nearby.

I was visiting chicago recently and went here twice. The first time was good, we didn't stay long but it left a good impression so we returned before I left chicago. I asked the older bartender what he would recommend as I didn't fancy my usual drinks. Long story short, history reply was that he doesn't know me so can't recommend anything. Thinking he was kidding, I laughed and asked him a second time. I hot the same stern reply so ended up ordering the drink I didn't want. I didn't get his name, but he ruined the experience of this lovely bar for me. I didn't give 1 star as the previous bartender was nice

This place is a good hole in the wall bar. Definitely gave speak easy vibes. It is cash only so be sure to stop at the ATM before. The door guy was so nice and inviting (Rafa)! The bartender (Jack) could have been friendlier. He was on his phone a lot… never really talked to me or other patrons. He also didn’t give me change on my $7 drink when I gave him a $10. Just assumed I’d tip him 30%. I work in the service industry, so it was just kind of weird. I’m an over tipper usually, but don’t just assume. Otherwise a great place and the patrons were very nice and welcoming.

left my drink when i went for a cigarette, asked the bartenders to keep an eye on it/take it behind the bar. when i returned, i finished the drink that was clearly spiked. i have never felt this ‘drunk’ in my life. tried telling the staff and got dismissed. avoid if you want to stay safe.

Great vibes, the bartender, Zac, is so friendly and outgoing. The bathroom has a blackboard and is so nice you can write your own message. Overall great place to go to anytime during the week!

I very much enjoyed this gay bar. Very intimate and had good music playing. Drinks are pretty affordable as well.

Fun small bar great spot step away from the chaos of the city and have a drink.

Surprisingly fun bar on the second floor, small but fit everyone just fine. CASH ONLY, they do have an ATM downstairs. Had a great time, bartender did an excellent job with drinks, heavy pour and reasonably priced. Will put it on my list for future visits. It's a dive-ish vibe and there was some eye candy at times. It got busy and guys brought their female friends who are very welcomed by the staff. Will be back.

Second Story Bar is a hidden gem just a stone's throw away from the bustling Magnificent Mile. Touting some of the most wallet-friendly drink prices in the city, this cozy dive bar beckons with its warm ambiance and lively atmosphere. Stepping inside at 3:45pm, the vibrant energy made it feel like prime time, complete with disco lights casting a playful glow and a bustling crowd adding to the convivial ambiance. Whether you're seeking a laid-back afternoon tipple or a lively evening out, Second Story Bar delivers on both fronts, making it a must-visit spot for any Chicago adventurer. #ChicagoBars #DiveBarDelight

I have been to this bar many times. Whenever I have friends in town I go here. Tonight, 5/14/2024 I brought an out of town guest and it was his birthday. We were sitting at the bar and my friend placed his drink down, but didn't notice the space between the bar and the bar rail, so his glass fell on the floor and broke. Immediately the bartender made a little scene and said "you're done". I thought he was joking and I asked him if he was joking. He said he wasn't and that he would no longer serve my friend because he broke a glass. As a bartender myself, I would never deny a patron a drink because of an accident like that. I could understand if my friend was intoxicated but that was not the case. So then the bartender started to get an attitude with me. I asked him to make me another drink with and he assumed I was going to share it with my friend and told me if I did, i was "done". I thought that was an odd thing to assume. Also, I asked him to make my drink with a certain liquor but he didn't hear me. When I asked him if he used that liquor he said I didn't ask for it. When I said I did, he then told me "you're done". It was a very strange experience. I am not sure what me and my friend did to this man. Anyway, not sure if I will go back to this bar or not. This left a very bad taste in my mouth and was very uncalled for.

The ambiance of the bar is lovely and I also appreciate some of the workers there-- very kind folks! However, I was shocked by the rude tone by the bartender who informed us that we must buy something or leave due to a larger crowd forming. I was fine with the request to purchase something, but the tone was very rude and unprofessional. Moreover, when I went to the bartender to purchase something, he made another rude and snide remark: "But there is two of you". I would have easily forgiven the first comment, but the second punctuated my issue: it felt very targeted and unnecessary. There were also other customers there who did not purchase anything either, but no comments were made in their direction. It was a cute bar when I attended the few times I did. Moving forward, I will not entertain the rudeness and unprofessionalism presented. P.S. they also have a very anachronistic practice of requiring cash only.

Lesbians are clearly not welcome here, took forever to let us in, the entire bar side eyed us, service was only given because they legally have to and you could totally tell, so much for solidarity

Down the narrow hall and up the stairs. If you thought that bougie speakeasy down the street felt hidden, try Second Story Bar. With just rainbow flags and neon lights you'll need strong gay-dar to hone in on this location. Or just ask around... or use Yelp. Lucky for us, we had all three. All are welcome, everyone was friendly and the drinks were basic but strong. No patio, decks, or fresh air here though, so it can get heated. Cash is king. But so is that shorty with the perfectly toned thighs.

I like this spot. Reminds me of dives back in late '80s & 90s. I slide in whenever I'm in Chicago. What ya see is what ya get.

Unassuming gay bar in Streeterville area, and to be quite honest, probably the only LGBTQ+ centered bar in the downtown area. I don't think River North or anywhere in the Loop has a bar like this. I'm quite surprised they don't honestly. I came here with a friend and this place gabe chill bar vibes. Definitely not a place you go to for dancing or twerking or any of that shenanigans. It's also very easy to miss. Walking up the stairs from the street makes you feel like you walking into someone's janky apartment and going up a flight of stairs. Anyways, ambiance was cool... our bartender was friendly, and just a reminder, it is CASH only. They have an ATM nearby downstairs so that wasn't an issue. If I'm in the area, it wouldn't be a bad place to grab a drink or pregame to go elsewhere, but don't expect Boystown energy by any means.

Cute little bar. Too bad it is cash only. The server was very nice. I would go back when in town.

What has a neon emoji signs of a fuzzy peach and an enlarged zucchini?! ... ONLY Chicago's Second Story Gay Bar! It's hidden upstairs via a nondescript stairway to the west of Sayat Nova's Armenian Restaurant in Streeterville. I had always wanted to pay a visit here when I was a local, however, never made it happen. Thankfully while visiting Chicago as a tourist I brought a gaggle of girls upstairs. Sadly many bars downtown and in the Loop aren't open very late, perhaps except in the Viagra Triangle area. It's always nice to not have to venture all the way north to Boystown for a gay bar. Upon entering, the bouncer was super cool and welcoming given my crowd and paparazzi. We hung out near the small space available nook near the front windows. It is not a large place but everyone was friendly and willing to squeeze in around one another. Second Story makes their drinks not only affordable but also boozy like most gay bars. We spent a few hours singing, eavesdropping to figure out each person's story, and judging folks as they came up the stairs via video surveillance. Oh and don't forget to bring cash! No plastic accepted.

Small, cozy, friendly, (and probably crowded) hole in the wall bar. Cash-only but ATM is just downstairs. Proof that good vibes don't need schmancy digs.

If you're from out of town this is a great speakeasy style bar to come to and have a STIFF drink! My friend from Fort Lauderdale suggested that we go here for afternoon drinks and it will not let you down! He was right! We were immediately served in this small upstairs bar with excellent drink prices and great service. If you aren't familiar with the area you'll have to look UP when your gps says you've arrived. There's an open door that leads up a staircase into the bar area. It was constantly packed with a bunch of people that are there to have a great time. Zach, was our exceedingly charming, entertaining and hilarious bartender throughout his shift. His personality had me encompassed awaiting his next words of reality! I definitely love this guy! If you're staying on the magnificent mile and looking for a place to go drink and hear Zach's playlist I think this place will be a perfect place to start from beginning til end. Trust me on this.

Great old dive bar in an out of the way place. Happy to hear that the bartenders are doing their best to protect the bar from being over run with bachelorettes! Cheap and strong drinks too.

Flight attendant and I were on a layover and we found this place. Dakota was amazing, super sweet and helped find my wallet. Also met some nice people. Only thing I suggest is bring cash, the atm downstairs wasn't working.

this is the cheers of the loop. fun mixed friendly crowd i've only been here friday afterwork but I love the bartender. he makes a great cocktail

The bartender was super rude and mean because we were girls. He pushed us out and screamed at us to get out and called us names. Never coming here again could give 0 stars if I could because the whole vibe and place was awful do not come here

I had a very poor experience at the Second Story Bar last Thursday night (11/02/23). Brian M. accused me of being rude when in fact it was he that was not friendly with me and my friend. At one point we asked if he carried Mexican beer and he rolled his eyes- the beer menu was no where near us so we asked. I always used may I, please and thank you whenever I ordered and at the end of the night, a gentleman offered to buy us around and unbeknownst to me Brian had called last call for alcohol when I was in the bathroom so I said I didn't know then he said I had to have my hearing checked and blatantly lied by saying I had been rude from the start which is clearly not true. Oh then I asked him for his name and he refused to give it to me -he said "Why so you can give me a bad yelp review ?" I ignored him and my friend and I left. After writing this, I noticed other people complaining about him and he is still there, speaks volumes of that place! Never again!

Super small bar But great location downtown Bar tender was super fun Great place to grab a drink No food

Cutest gay bar I've ever been to! Down a hallway and up a flight of stairs next to a restaurant and you're inside a charming little gay bar on river north. Friendly staff and affordable drinks. Just around the corner from my hotel it was the perfect bar for my evening

My favorite bar in the country. Everyone from the staff to the regulars are fun and welcoming.

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

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.

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.

Great unassuming bar. Really easy to miss (good). People super friendly. Always great fun!

I usually visit this place every time I'm in Chicago and with my friends or as a night cap and it's always been a very nice, gay friendly place to just hang out and have a few drinks. I understand that on this night maybe I did not get the "no females" memo, however the cold and harsh way my partner and I were treated is just unacceptable. Any lesbian forward bar welcomes gay men ALWAYS, it's just sad this was not reciprocated this night. Thank you for making my girlfriend feel uncomfortable and unwelcome. Bad look for the community. We're on the same team.

Perfect local hangout it's a place we're everybody knows your name and your drink and most importantly they look forward to seeing you. I love the cast of characters that really enjoy each other's company.

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

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!

A neighborhood joint downtown. I have a blast every time I wander in. Friendly, fun, dishy. Yeah, it's a total gay bar, but like any place else, if you are friendly and fun, you're welcome most anywhere. If you're a Lincoln Park Trixie, celebrating your bachelorette party, don't come here. Seriously, no one wants that idiocy in their establishment. It's just off the Magnificent Mile, and this bar is probably the most authentic thing in a 12 block radius in this area.

We came here late on a Saturday night, primarily because this bar is open until 3 a.m. when most close at 2, and it was within walking distance of another place we'd visited. We entered, walked up the carpeted staircase to the second floor, went into the bar space and were met right away by the bartender. We each ordered a drink, and prices were about average for a downtown bar. Note that this place is cash only; they don't accept plastic. While I liked the Second Story Bar, know that you're not coming here to dance or be entertained. You're coming here to drink, plain and simple...And maybe chat with whomever else happens to be at the bar, or watch whatever they happen to be showing on the TVs. This place is relatively small, definitely a touch on the divey side, and the bartop is a bit worn and the varnish scratched up in some areas after years of use...But it's pretty well stocked and they have some unique looking lamps attached to the bar top that are made out of plumbing pipes and fittings which I thought were really cool and imaginative. As we were finishing our beverages they turned on the "ugly lights" as they were ready to close. We asked if there were any other places in the area still open, and the friendly staff here gave us a great recommendation.

I used to be a regular at this bar. To be honest, I probably have only been in the bar five times in the last 12 years. I came in for the first time in two years in July. Brian was the bartender and was ice cold......... bordering on rude. I can live with not being welcomed with open arms. I'm no longer a regular, to be fair, but he was put off by my mere question about their specials and the only way I can put it would be that, somehow, arriving at 2:30pm was interfering with his little clique of old sots that hang out daily at that early afternoon hour. I want to preface, I didn't ask multiple questions. It was like 10 words in the 45 minutes I was there, but it was met with a coldness I will not soon forget. If this is how non-regulars are received it leaves much to be desired. I may go in when Zach is there....if he still works there. Hopefully he's moved on to better things.

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.

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

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

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.

"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.

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!

If you're in the mood for cheap [strong] drinks, a casual atmosphere, and friendly people then the Second Story Bar is the bar for you. It's a small, divey spot but that's what makes it all the more fun. People are friendly and the bartender is more than generous with the pour if you're not an a$$hat (which is really not hard). Good selection of beers too!

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!

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.

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.

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.

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

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.

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!

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.

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

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.

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.

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.