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The Flat Iron

3.5 star rating
based on 24 reviews

Category: Nightlife  [Edit]

Neighborhood: Wicker Park
1565 N Milwaukee Ave
(between Damen Ave & North Ave)
Chicago, IL 60622
(773) 365-9000
Nearest Transit:

Damen (Blue)

Parking:
Street
Accepts Credit Cards:
Yes
Price Range:
$
Good for Groups:
Yes
Wheelchair Accessible:
Yes
Outdoor Seating:
No
Music:
Juke Box
Best Nights:
Tue, Fri, Sat
Alcohol:
Full Bar
Smoking:
No

24 reviews for The Flat Iron

Review Highlights   

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"they've got pool tables which is just perfect for drunken exhibitionism." (in 6 reviews)
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"Also, they stay open until 4am on weeknights." (in 6 reviews)
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"a little hipster, but I would definitely go back." (in 4 reviews)
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Sort by: Yelp Sort | Date | Rating | Elites'
Photo of Jaik S.

Elite '09

110

79

Jaik S.

Chicago, IL

4 star rating
11/18/2009

Whether you're leaving a party, or being escorted to the door at closing time while drinking at your local bar, there is a solution to continue drinking. You head to one of the bars that are open late.

For me, the closest one that's open late is Flat Iron. I've been in here when it's almost empty, I've been in here when you can barely move. The benefit is that there are two bars in here, and so when you don't get fast service at the front one, you can go wait at the back bar.

As for the crowd, I've seen all types here. They all want to be up late drinking. If you do end up here, let me know, I'm just down the street.

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Photo of JeeJee A.

 

6

50

JeeJee A.

Chicago, IL

3 star rating
11/17/2009

Anywhere else, this would be a regular dive bar. In Wicker Park, this is an overpriced dive bar that's crammed to capacity with douchebags.

The highlight of my sole evening there was getting to shut down the creepy old dudes that tried to hit on my best friend and me. YOU'RE OLD. WE ARE YOUNG, ADORABLE AND CLEARLY OUT OF YOUR LEAGUE. Such a hearty lol. Oh, someone also put on Killing Joke and Ministry, bless their dark little heart.

Sadly I would take this place over Debonair or any of the other stupid bars here, but that's not saying much. Because their music is more tolerable and there's a pool table, this is probably my preferred heckling destination in Wicker. Yes, heckling. Trying to make friends/find potential mates at bars is lame, get with it, ya'll!

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Photo of Maggie E.

 

6

9

Maggie E.

Chicago, IL

3 star rating
11/7/2009

When I rolled over to give Flat Iron 3 stars, Yelp told me that means "A-OK", and I thought, "That sounds about right."

Flat Iron is exactly what it's supposed to be, I think. No "Identity crisis" that a lot of yelpers seem to like to talk about.

So I gave three stars because it's totally not MY scene, but I can definitely put up with it when that's where all my coworkers want to go after work, and, for some reason, I still feel like hanging out with them.

Okay, specifics Maggie. C'mon.

It's a very large space which is great for the waves of people who want to pack in there after 2am. There are pool tables which people will comically continue to play on even at 3am when everyone's bumping into each other.

The staff is clearly busy, yet I have always had a drink in my hand while there, so they're obviously taking care of business. Also, with the large space, it's nice to see multiple security guys overseeing everything.

When I don't feel like listening to whatever my coworkers are talking about while we're there, I like to look at the neato artwork on the walls. I'd describe it more but I always leave pretty drunk and I don't remember clearly enough.

And while a lot of my guy friends often complain about bars being sausage fests (hey, I'm totally down with sausage fests), I've noticed there's a decent amount of chicks wandering around. In fact, a couple nights ago, as soon as I left my two dudes to grab a smoke, there was a chick sitting with and hitting on one of them when I got back--and I smoke FAST. So guys, take that as you will.

I should go in earlier, sometime, because I'll bet I would really like it then, before all the drunks stumble in.

So, yeah, it's totally what you'd expect for a 4am joint by the six corners in Wicker Park. After 2am, loud, busy, and (for me) obnoxious, but you'll still get your drinks and, it seems, maybe get lucky if you play your cards right.

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Photo of Rod J.

 

2

49

Rod J.

Chicago, IL

1 star rating
11/9/2009

One word "suck(s)".
People suck, place sucks, prices suck, music sucks, the scenery sucks, neighborhood sucks. There is not one good thing to write about this place. You're better off drinking a bottle of piss from one of the local bums in the alley by yourself then going into this dump.

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Photo of Krissy V.

 

3

5

Krissy V.

Chicago, IL

4 star rating
11/13/2009

Usually if i am here that means i should have gone home about an hour ago.  This is the only 4am bar in Wicker Park that doesn't make me feel like a total scumbag being at.  The music is pretty good and the fact that there are 2 bars makes it easier to get a drink when the early bars close. I have seen people puke in this bar on more than one occasion. No biggie though. I also like the fact that it is huge so you can avoid people if need be.

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Photo of Richard D.

 

4

42

Richard D.

Chicago, IL

5 star rating
8/18/2009

Thank you Flat Iron for proving that Wicker Park isn't as bad as people say (over gentrification, hipster/frat boy assimilation, etc. )

I fucking love the guerilla style urban artwork thats covered all over the walls. It kind of reminds me of that obscure MTV show "Downtown" from the late 90's that I used to love. The whole place just screams "cool hip bar" without scaring you away with some superiority complex. The crowd is a great mix of different scenes, and ages. It doesn't matter if 25 or 35, or if you're sporting a Marc Jacobs hoodie or an Iron Maiden t-shirt. This place is perfect for social gatherings, great drinks, great music, and great for people watching (like a gaggle of hippies and nerds drunk karaoking to Soul Asylum)

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Photo of Steve R.

Elite '09

103

465

Steve R.

Chicago, IL

4 star rating
6/5/2009

I woulda sworn I wrote a review of this place already.  Went in here on a Yelper pub crawl the first time, and the second with some other friends.  First time I thought it was more or less exactly the same as the Note, with some extra art on the walls and no stage anymore.  S'ok, drinks average priced, taps standard for the 'hood.

The second time.I came it was the one oasis in the hood that I could walk in and hear The Stooges, Helmet (their good first record), and stuff of that ilk. Me happy.  PBRs cheap if you're on a budget, and they have better stuff on tap if you're not.  I'd happily hang out here, wasn't too crowded but not dead either on a weeknight.  I think they had someone DJing rather than a jukebox, but I could be wrong. Anywhere I can get away from "untz-untz-untz" or that jangly no-testes shit that seems to rule the earwaves these days is a-ok with me.

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Photo of Kristen F.

Elite '09

15

74

Kristen F.

Chicago, IL

3 star rating
5/30/2009

This is obviously not a place where I would fit in. I went here for some Melvin's art show put on by a tattoo studio for the School of Rock that was pretty good.

I am not going to judge this place based on what I would like in a bar - you know.. nice bartenders and cheap strong drinks and a crowd that borders on annoying but doesn't really get all up in my face.  I mean that would be silly, right?

It's a bar so it did the trick. The bartenders served drinks, even if they did it with this "What the fuck you doing in here with that cardigan and that face?" attitude.  The crowd had fun, even if they did it in this "What the fuck are you doing here with those jeans and those shoes?" kind of attitude.  

I knew I should have worn that flannel I still have from 1994 and those tight jeans my mom had left over from 1950. Maybe then I would have been hip enough to be in here. Seriously, is this the backroom to a shitty venue where everyone is waiting for their turn to get on stage?

Extra star for the decor, the extra bar when it got busy and the pool tables.

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Photo of kara c.

 

0

7

kara c.

Chicago, IL

3 star rating
9/26/2009

I have no real issues at Flat Iron. Around 2am it gets pretty cool, but dead before then. The prices are usually 5/5 but that's what to expect. My only tif is that don't know how to make proper mixed shots. The crowd is always changing and I like that a lot. Also, they stay open until 4am on weeknights!

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Photo of Ted D.

 

46

176

Ted D.

Chicago, IL

4 star rating
3/24/2009

I am pretty sure it was a Friday when we came here.. yes I was in that state of mind..
But I remember this place being MASSIVE and PACKED. Not a bad thing, I actually thought it was awesome that they could bring in such a large steady crowd. It really wasn't that bad of a place, I am sure I will be back when in the area again.

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Photo of alicia g.

Elite '09

19

70

alicia g.

Chicago, IL

1 star rating
9/22/2009

This place SUCKS. I HATE this place. Whenever anyone I know suggests going to the Flat Iron, I know they are only suggesting it because their drinking habits have hindered their abilities to make good choices about anything and everything, including which bar to go to. I've gone here twice, and both times I have been so embarrassed about being there, that I have left within 30 minutes of arriving. The first time i was introduced to my friend's friend from college...who also happened to be a stripper. The second time, there was a chorus of hipsters singing along to Slayer while spilling their PBR on everything and everyone. Gross people, gross people with tattoos, and dirty hipsters with gross tattoos. No thanks. If you do plan on going here, don't shower for a week, get a face tattoo or some stupid ironic mustache on your finger, and go to AmerPer (AMERICAN APPAREL) so you can fit in with the rest of the usual crowd that hangs out at this stupid bar. Also, I did give it one star because I like that their electronic juke box plays Black Flag.

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Photo of James V.

Elite '09

21

51

James V.

Chicago, IL

5 star rating
5/8/2009

I mean, how can you complain about the Flat Iron.  With it's dirt cheap drinks, copious amount of space, plentiful pool tables, and 4am closing time, it's a case of love at first shot.

The have a solid no frills aesthetic that works perfectly. The staff is nice and pours heavy. And they're open when all the other bars close, so it's really a mixing pot for the neighborhood.  Between this place and Pint, you can meet everyone who parties in the neighborhood.

The flat iron is a great place, I recommend you stop in on your next foray into wicker park.

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Photo of erica w.

 

5

9

erica w.

Chicago, IL

3 star rating
7/7/2009

Best people watching bar I've been to in a long time...this place is more than just a melting pot, it's like fifty years worth of pop culture, music and fashion just threw up all over it. Nonetheless, drinks were strong, music was good. Great after hours spot if you're in the area..but be prepared for hipsters galore!

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Photo of Christine N.

Elite '09

96

359

Christine N.

San Jose, CA

3 star rating
8/17/2009

Super divey with pool tables and lots of seating. Perfect place to just chill out!

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Photo of Megan W.

 

6

48

Megan W.

Chicago, IL

3 star rating
4/9/2009

I had one really fun, really good experience here, and one that wasn't so good. Well no, it was good--but let me explain. The first time I went here, my best friend and I were accompanied by a guy friend. Had a blast. Second time, just the two of us--and had some very serious problems with skeezy men--particularly with this one guy who thought it was still 1998, dressed like fred durst, and wore man-liner. Strange strange experience. Just came up to us and started yelling incoherently-got in our faces, and said, "hold my drink bitch", if I remember clearly. I walked away. Now remember, we didn't say ANYTHING to this guy. It was completely out of nowhere.
ahem.

The second guy was this douche hitting on my friend--he had an "irish" accent--but my theory is that he was really just some ass from westmont. It was like seeing ben affleck trying to do an irish accent.

My advice--good 4am bar--but only if you have brass knuckles or a guy friend to hang around with.

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Photo of Alice S.

 

15

9

Alice S.

Chicago, IL

3 star rating
5/2/2009

I really want to like the Flat Iron, but from the moment I walked in, I felt like I was walking onto the set of Less Than Zero.

I give them bonus points for being spacious, but then I subtract them for having every spacious square inch filled in with dudebros that remind me of every bad guy from every Karate Kid movie ever.  The drinks are nothing special, but the internet jukebox is nice (assuming somebody doesn't put in $5 worth of ska); however, that's simply not as charming as a real jukebox made of well thought-out selections.  Instead, it's really like some random girl on myspace who lists every band she's ever heard of with the hope that some random dude will be like "Ohmygod!  I like (insert band here) too!  Let's bang!"  In fact, I'm pretty sure I overheard that exact statement there last night.

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Photo of Sia B.

 

8

17

Sia B.

Chicago, IL

4 star rating
4/18/2009

It's nice to have a place to stumble into at 2am on the 6 corners besides Estelle's...I like  Estelle's, but there's never been a wait to get in here.
It's big enough, there's always a decent crowd, and good tunes.  Apparently there's a sleeze factor to be warned about for  the ladies, but Imagine  that's with many 4am's.

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Photo of Paul C.

Elite '09

9

66

Paul C.

Chicago, IL

4 star rating
3/16/2009

I came here before when it was the Note.  The door guy told us how they changed the name and ditched the live music scene because somebody got stabbed with a broken pint glass in the bathroom.  A little upsetting, because I wanted to play here.  They have pool tables for $1.75 a game.

FOOD: Not sure

DRINK:  They have Three Floyd's Gumball Head.  My friend opened a tab and I really don't remember leaving... just woke up in my bed with my coat still on and all the lights on.

ATMOSPHERE:  I had a great time.  Just shootin a few games of pool with my best friend.  Music was ok.  the art on the walls is pretty cool.  Alot of that abstract city/graffiti style art.  Something you would see on the cover of a hIp hop record.  The bathroom stall didn't have a door on it which made some things rather awkward... but duty calls.

I hear this place gets totally packed, probaby like every other hipster location in Wicker Park.  I went on a Saturday afternoon and it suited just right.  if I'm in the neighborhood, I might go back.

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Photo of Matt R.

 

6

7

Matt R.

Los Angeles, CA

4 star rating
6/17/2009

4 shots of Jameson for $20  I'm just saying!  And it closes at 4am

Great dive bar in the middle of a lot of somewhat trendy stuff.  I agree with James V

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Photo of Nancy S.

 

3

4

Nancy S.

Chicago, IL

3 star rating
7/25/2009

Almost always the same but if its after 2. Its probably the best place in wicker. Plus decently cheap

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Photo of Babs H.

Elite '09

22

123

Babs H.

Chicago, IL

4 star rating
4/23/2009

Finally! A bar in Hipster Haven that doesn't make me want to stab my eyes out with blunt objects! The tunes were good, the decor is rad, the crowd wasn't obnoxious, and the people that I knew there I liked! One of the bartenders was a bit of an ass when I told him I couldn't taste the whiskey in the drink he had made for me, but the other guy was pretty awesome and threw an extra ounce in it for me.

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Photo of Dave C.

Elite '09

7

74

Dave C.

Chicago, IL

4 star rating
2/15/2009

there's just something about this place that i really feel. maybe it's the spaciousness of it or the art on the wall, but i dig this place. it never seems to get too packed and it makes me wonder what the place looks like on a weekday. they've got pool tables which is just perfect for drunken exhibitionism. one of my favorite moments here is when i was in the restroom and a guy suggested i leave because he said something to the effect of,  'i'm going to make a mess of sorts.'

thank you for the suggestion, sir.

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Photo of Curtis J.

 

0

6

Curtis J.

Chicago, IL

4 star rating
8/24/2009

good feeling at this place. good mix of people. a little hipster, but I  would definitely go back.

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Photo of kate w.

 

0

9

kate w.

Chicago, IL

3 star rating
1/1/2009

the flatiron has sometimes been a good place to drink after hours, but sometimes they are just crazy!!!  like my out-of-town sister came in with me one time and there were like 20 people in the whole bar and we walked up tp the bar wirh 4 people.  she jokingly ordered 17 jagermeister shots and instead of the bartender looking at our small group of 4 people and asking "where are the other 13 people?"  he started pouring a bunch of shots...
as a bartender myself, i would have asked that question, but what the heck.
anyways, the bartender, then lectured and chastised my poor sister, in from out of town on her honeymoon- a vacation i had invested quite a bit in, and that bartender single-handedly made her feel like she did something wrong even though he could have maybe deduced from her smile and general demeanor that she was just goofin.  but i guess common sense doesn't count for much anymore in this litigious world we live in.   if she says 17 shots and the bar is empty and only 4 new people walked in- i'm just gonna do what they say...  
i wanna like this bar cuz it's big and spacious and has great artwork, but  besides that instance, i've had a couple questionable interactions with the staff there.  i'm a  bartender too, and understand general bar etiquette, and i think they could be a bit more welcoming and accomodating.

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