The Flat Iron

Bar · Wicker Park

The Flat Iron

Bar · Wicker Park

3

1565 N Milwaukee Ave, Chicago, IL 60622

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The Flat Iron by Infatuation - Reviews
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The Flat Iron by null
The Flat Iron by null
The Flat Iron by null
The Flat Iron by null
The Flat Iron by null
The Flat Iron by null
The Flat Iron by null
The Flat Iron by null
The Flat Iron by null
The Flat Iron by null
The Flat Iron by null
The Flat Iron by null
The Flat Iron by null
The Flat Iron by null
The Flat Iron by null
The Flat Iron by null

Highlights

Funky bar lined with local art draws an eclectic crowd for drinks, billiards & jukebox tunes.  

Featured in The Infatuation
Featured in Eater
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1565 N Milwaukee Ave, Chicago, IL 60622 Get directions

$ · Menu

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1565 N Milwaukee Ave, Chicago, IL 60622 Get directions

+1 773 365 9000

$ · Menu

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Last updated

Jul 12, 2025

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@eater

"Flat Iron set up a fund that aims to raise $3,000 for staff who depend entirely on the venue for income." - Naomi Waxman

How to Help Chicago Bar and Restaurant Workers During the COVID-19 Outbreak - Eater Chicago
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@infatuation

"The Flat Iron is much louder and grungier than a lot of the fancy cocktail bars you’ll find near this Wicker Park intersection, so you shouldn’t come in expecting great drinks or stunning hospitality. It’s just a 4am bar that’s usually playing hardcore music, with walls covered in murals from local Chicago artists. But along with the typical pool and darts, they have skee-ball, a shuffleboard table, and Big Buck Hunter." - josh barnett

15 Bars With Things To Do Besides Drink
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@infatuation

"Even though it’s surrounded by pricey boutiques and speakeasies that serve artisanal cocktails, The Flat Iron isn’t fancy. It’s just a 4am bar that plays loud music and has enough activities to keep you drinking here for hours, including pool, darts, skee-ball, shuffleboard, and Big Buck Hunter." - Josh Barnett

The Flat Iron - Review - Wicker Park - Chicago - The Infatuation
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Jinny Gunn

Google
Let me say this about that....I was back in Chicago for work and doing the tourist thing. I had great pizza, went to Jack's Pop up Pumpkin and the Improv. Since it was Fall back and I got to enjoy an extra hour, I went walking down Milwaukee. Unfortunately, my paper bag (save the Earth) of souvenir crowlers busted open & I found myself carrying them along w the associated pint glasses. Tried to get into Nick's Biergarten, only to be told twice, no way, get outta here w those, even AFTER explaining the obvious. Walked just up the road to the welcoming arms of The Flat Iron staff (thank you tremendously Tom) who not only saw the situation for what it was, but provided a new carrying satchel and excellent environment. HIGHLY recommend for those desiring a laid back & enjoyable experience. Shot pool, drank cold drafts at great prices & meet cool people. Thank you for being reasonable people!!

Stephen Suydam

Google
This is a divey joint with a metal feel. The staff are characters and great for a chin wag. Happy hour specials and shots of the day will get you lit if that is or is not your goal.

Nia Watts

Google
Loved the pool games only being $1.50 per table! We went on a weeknight so wasn't hard to find a pool table so not sure how it is on the weekend. Great drinks. Staff is very friendly and engaging. Hubby and I enjoyed our time here and admired the wall art.

Skanky Trick

Google
They have 3 pool tables (all 8-foot). That is nice. The floors that slope in every direction are NOT nice for playing pool (for me, anyway). The people are decent, as are the staff. Most of the pool players are more arrogant than their talent should allow, but with 3 tables, at least you have options. There's usually a wait on all tables, and on weekends it just gets crazy. Prices are what you would expect for the area. They're open till 4 am, so I go to shoot pool after my 2 am spots close. DON'T PARK ON MILWAUKEE — YOUR CAR WILL BE TOWED! I PROMISE YOU.

Justo Diaz

Google
Have been here a few times all of which are great. They have 3 pool tables with chalk boards to call next game. I think it's $1.50 per game, which is higher than average but still less expensive than other pool halls who charge hourly. This place does get packed Sat nights! You might have a hard time finding a table. Has 2 bars. Bathrooms are small. Also, bouncers ready to bounce anyone who has had too much. Great vibe from the people and music. I see myself coming back here!

Chris Krolczyk

Google
Nice, dark semi-dive atmosphere that compares nicely to spiritual brethren like Crown Liquors or the Revel Room. Two bars, pool tables and a great deal of space that I couldn't find at the last two bars I deemed as way too crowded. Decent selection of music on as well.

xClick ITx

Google
Cheap drinks, open late, good staff. On a few lucky nights you can find the tamale vendor walking around. Chicago handshakes are where it's at. A lot of pool tables for those interested. Great place to have a few drinks and enjoy the neighborhood. I recommend stopping in.

Ronald Jackson

Google
Could have been awesome!!! Layout and game availability is great. Nice traditional sports bar atmosphere. Walked in sober and waited for our first drink and apparently stood in the wrong spot at the bar as an employee wearing a Cabrera 24 jersey walked up and said to the bar tender over our shoulder "we need a f**king sign that says mother f**keys shouldn't stand here" either thinking we couldn't hear or as a passive aggressive way of making us move. What an unpleasant way to start the night!