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Pie Hole Pizza Joint
737 W Roscoe St
(between Elaine Pl & Halsted St)
Chicago, IL 60657
(773) 525-8888
- Nearest Transit:
-
Belmont (Purple Express, Brown, Red)
- Hours:
Mon-Thu. 5:00 p.m. - 3:00 a.m.
Fri. 5:00 p.m. - 5:00 a.m.
Sat. 11:00 a.m. - 5:00 a.m.
Sun. 11:00 a.m. - 3:00 a.m.
- Attire:
- Casual
- Accepts Credit Cards:
- Yes
- Parking:
- Street
- Price Range:
-
$$
- Good for Groups:
- No
- Good for Kids:
- No
- Takes Reservations:
- No
- Delivery:
- Yes
- Take-out:
- Yes
- Waiter Service:
- No
- Wheelchair Accessible:
- No
- Outdoor Seating:
- Yes
- Good for:
- Late Night
- Music:
- DJ
- Best Nights:
- Mon, Wed, Sat
- Happy Hour:
- No
- Alcohol:
- Full Bar
- Smoking:
- No
- Coat Check:
- Yes
63 reviews for Pie Hole Pizza Joint
Review Highlights
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Love me some Piehole.
Drunk Tiffany: 3am bar close -- I am a human vaccuum...where to go for food? Well, if I'm anywhere near Roscoe and Halsted, I am drawn to Pie Hole like a (pardon the cliche term) moth to a flame....pizzaaaaaa. There, my date or friend can see me grossly suck in a slice of sausage or pepperoni pizza in record time. Come on...when you're wasted, you need meat and social courtesy goes out the window. PS. Waiting for pizza here is great for my self esteem, on many occasion, a beautiful man will tell me I'm adorable. (I don't care if it's 3am, and they don't really mean it...I just like to hear it!) However, very rarely am I his type due to what nature graced me with. Where are the ladies? No clue.
Week Night Sober Tiffany: I've never eaten in the actual restaurant sober, but I've ordered delivery many a times when I lived in Buena Park. The pizza is always great. I've tried several of the specialty pizzas:
White Party: It is a party in your mouth. (Forgive my corniness.)
Angry Pesto: Omg...omg....oooo eeemmmm geee. Just thinking about this...I'm hungry now.
Miss Foozie's Signature Pie: Pretty good.
After School Special: No, I'm too scared to try it.
I'm happy to pay the extra $ for Pie Hole...it's worth it. When I discovered Pie Hole, it became the only place I'd get pizza from. Still is whenever I want pizza while visiting my "Red Line" friends. Only complaint: pizza does get a little cold by the time it comes to my doorstep when I order delivery. That, and no Blue Line location...guess I'll just settle for Piece when I'm sober, and Mexican food when I'm wasted at 3am. Ok...enough said. Time to shut my Pie Hole....ok, I'm seriously done with the cheesiness. Mmm...cheese.
It's probably slightly unfair to rate a place based on a first encounter in which you were intoxicated, after all, almost any food is better when it follows liquor, beer, or um, other herbal substances (what? I'm talking about green tea). But I will rate it with that first impression in mind anyway. Because I want to. And because it's not against TOS.
Pie Hole is a great place to come to for a late night snack or an early dinner (they don't open until late afternoon/early evening). The slices are pretty good, and while still deliciously greasy, they seem slightly healthier than the Baccis, Gigios, and Ian's of this city. I cannot tell you why this is- and I may just be pulling it out of my ass to make myself feel less guilty for the carb-overload I partook in today. It is what it is.
Okay, so with the necessity of tasty pizza out of the way, Pie Hole has other pluses. The available liquor is pretty cool, but I think of it as a pizza place foremost (I'm guessing by the name so do the owners), whereas if you're actually coming to it with the mindset of it being a bar, that's not so amazing. I also enjoy reading the t-shirts hung on the wall that are covered with sayings like, "the best 10 inch you'll find at 2 am" and something or other about a "large sausage."
While the decor, saucy sayings, and fun, slightly manic soundtrack are nothing especially unique to Boystown, I like it as a side to my (pizza) pie. I will, however, have to deduct one star because I think that it's a little pricey for what you get. Oh, and also because the employees need to be a little bit more diligent when it comes to getting extremely drunk and tone-deaf people off the stage on karaoke night.
seriously? it's halloween. it's halloween in boystown and you're at the end of the halloween parade route. it didn't occur to you to make extra pizza? how is it possible that you have a line of people out the flippin' door and you have 2 slices left? that's it... two. two paltry slices of pizza and they're both sausage?! fer realz?
three of us pop in post-parade to warm our freezing fannys and fill our empty stomachs. one grabs a table while the other two (including myself) make our way through the long and crowded line only to be verbally assaulted by the drag queen behind the counter. after seeing that there are only two slices, i decide to take them both, alas there was nothing for my vegetarian friend to eat since, as i mentioned before, both slices were sausage. back to the point... i order my 2 slices along with 3 beers. i show my id, my friend shows his but due to our lack of 3 SEPARATE ids, we are only allowed 2 beers. fine, whatever, rules are rules. the nasty queen behind the counter begins ringing up my order when i notice she has only charged me for one slice. i tell her that i asked for both and she yells "no... you only asked for ONE!" then proceeds to "accidentally" spill the beer all over me.
i did get a replacement beer, the pizza was edible and i did get to spend a few minutes inside warming my feet, so i guess it wasn't a complete loss.
I have tried and tried to give this place a chance, but they are ridiculously slow and most of the time the staff is too busy on their cell phones to give you two seconds of service. I have written the owner and haven't gotten a response at all - save yourself some money and time and go to Jewel and get a tombstone - it tastes better anyways
1 Previous Review: Show all »
-
8/27/2009
I have tried to give this place a chance being in the neighborhood and all but some of the employees… Read more »
After a night out in Boystown there is always the empty stomach dilemma before you go to bed... Options are little. Full meals are out of question! It's either midnight burritos (A real bomb in your stomach!) or Pie Hole.
Irreverent as it is, Pie Hole is absolutely awesome! Their pizza is delicious all way around! From crust to toppings (not to mention their delicious sauces) this is, hands down, the queen of the pizzas in all Lakeview!
Their slices are huge! The place is small but fun, and no matter how drunk and annoying you are, they'll always serve you with a smile!
To be fair to Pie Hole I would have to review it based on two different persona's: Sober Kito and Six Sheets to the Wind Kito. Two extremely charming individuals that don't agree when it comes to Pie Hole.
Sober Kito: Doesn't really care for this ultra flashy pizza joint that yells were gay friendly the minute you walk in. And, no I'm not judging the place on its homo friendly environment, because I'm a huge Liza Minnelli daughter of the great Judy Garland loving mo myself. I'm judging the place on the quality of the pizza and its just average, nothing special. The only plus side is that you can purchase individual slices and the portions are very generous. Unfortunately, the pizza leaves lots to be desired.
On the other hand:
Six Sheets to the Wind Kito: loves himself some Pie Hole. The main reason is that its open late and when you just finished a six hour binging excursion in Boystown a large slice of pizza sounds fabulous. If I'm eating at 2am I can guarantee that I'm not eating for taste but to fulfill my drunken food desires.
Based on those two persona's I averaged out the star rating and gave Pie Hole a astounding 3 stars.
Never been to the joint but order it for delivery at least once a week. The wait time is a bit longer and the price higher, but what one gets is easily the best pizza I've had in Chicago, and yes, I've tried nearly all of them.
The tomato sauce is sweeter, which may turn some off, but, for me, it was reminiscent of a pizza I grew up on back home in Indiana. Perfect balance with some savory toppings.
Also everyone I've dealt with on the phone and in person for the delivery have been very nice, helpful, and deserving of a fat tip.
Cocktail was advertising strippers last night so that explains why we had to press the flesh to get into Pie Hole.
Yeah, I said it.
I've been to PH a few times. . . sober to boot. They used to be BYO, which would have lent another star. Sitting on Roscoe, watching the short shorts, mirrored glasses and biceps was free entertainment. With 7-11 within spitting distance, we could replenish alcohol on a whim, meet a new friend, crack a glowstick and get on with it.
But this time we were sober, famished and not in the mood to pay for booze. As is requisite in B-Town, the techno thump was everpresent in PH. The service was aloof at best, the clientele was amusing as always, the pizza was still mediocre. We ordered a sausage and goat cheese pie and a pepperoni and red pepper crusty round. Sadly goat turned out to be ricotta which has no place on pizza. It finds its way into my belly in plenty of other ways.
On the corner of Gay and Wad, PH is a staple. They sell by the slice and they're patient with tweakers, femmes, Bears and everything in between. It's charming and cute and flirty and never subtle. . . but don't waste your time if you're not looking to push the tush with man, woman or otherwise. And PH does love the otherwise in all of us.
They'd get five starts, but the pie hole they put in my wallet is killer!
Seriously, this pie is awesome. Went here last night for the first time in a long time and had a mushroom and banana pepper pizza - yummmmmi...
Their pies are awesome and made better/worse by the movie being shown on their tvs. Last night was "Boogie Nights" so needless to say Markie Mark sticking it to em as Dirk Diggler wasn't helping my mushrooms go down any better, but its Boystown, I love it.
The beer selection is decent and goes wonderful with the pizza as well. I had a Heineken and yet don't know why since we had just left Joes on Broadway...
The pizza here though is some of the best 'regular' style pie I have had in the city. Big slices, fair amounts of cheese and good crust. I love this pie hole like no other and you should to :)
Full disclosure: generally when I have partaken of Pie Hole I have been quite intoxicated. Let me re-phrase that- all the times I have partaken of pie hole I have been intoxicated.
That said, their pizza is hella good! Really nothing is better at 3 in the morning than one of their creations. I am dying to try- sober- some of the made to order selections, as they seem a good bit more daring and innovative. I don't live in the 'hood so this would be a dine it experience. Additionally, Pie H features some clever week night specials, that supplement their pizza offerings with cocktails etc. Thumbs up to that!
As for the pizza- tres tasty! You are talking to a devotee of the NYC style pizza. Basically, I don't like the Chicago style mess. PH produces a firm crust, paired with a tasty sauce. Basically just right. As for the service- if you don't like it I'd advise you to shut your pie hole, b/c you'll never get your pizza.
In short I am looking forward to returning sober.
I've been to Pie Hole a few times. After all of those trips I can say that while Pizza is ok, Tuesday all-u-can-eat pizzaby the slice pig-a-thon is good, their staff on the other hand (not everyone) is pretty "discouraging". Lack of friendliness and a "I'm doing you a favor by standing behind this damn register" attitude does not help. Two people that I like there are Ronnie and another blond girl with long hair (sorry but I forgot the name). They're always nice and cater to all requests - they know that it's the customer that puts the money in their pickets. Last time I went there with two of my friends on October 19th. The slices were out so we asked how long it would take for the fresh batch. The guy behind the register mumbled something that we had no clue how long it would take. We decided to wait a few minutes. After that we left. Since there was nothing else available for a quick bite (9 pm) we went back. Ordered two slices and again the reply was something mumbled under his nose. We waited about 15 minutes. Two guys that came after us had their pizzas handed to them while we kept waiting. Finally the pizza was out. It was practically thrown in front of my friends with a shitty "Here you have and f-off" attitude. I like pizza, and probably will go back there but the bitchy attitude and a lack of courteous service needs to change. If I was the guy, who owns the joint, I'd definitely re-train the staff and teach them some manners.
An excellent inebriated slice of pepperoni and sausage pizza. Just the right combination of sauce and sweet, salty and cheese. I like that they give you foil under it so there is no leaking of ingredients as you walk. I'll be back often late at night.
Amazing staff, amazing spicy pesto pizza, breadsticks to die for!
My first time didn't hurt at all and I'll definitely be back to take more meat!
Ok Ok, I've been here enough times to say that I should learn when not to go back. But...seeing that most of those experiences stem from long nights out in Boystown, I can't really be held to blame, as alcohol impairs my judgement on what good food actually is.
I will say that if you've had enough to drink, and all of a sudden you have that urge to eat greasy food, then go here. It's close by, it's open late, and you'll still have time to hit up another bar in the process, if time permits. Otherwise, I avoid it.
The place is small...really there are only a few stools and maybe some outdoor seating if the weather is nice. otherwise, I took everything to go. I know they serve alcohol, but really...with all the bars around, would you really want a beer here?
The pizza isn't all that great, but when you're intoxicated, you can't really tell until the next day. The pizza does not save well in the fridge either, so if you're expecting a great pizza breakfast after your hangover, then try something else, because this stuff just doesn't work for some reason.
I have a ton of coupons for this place, so the price doesn't deter me too much, plus I had a friend who worked there a few years ago, and would hook us up with free slices (a secret that I am sharing with you lovely people now). But really, with the quality of food you're getting, the food should be free anyway.
Mister and I are great lovers of pizza, so it's no surprise we started trying pizza places almost immediately after moving. Pie Hole was the obvious first choice, as it's like a block away from our place. It was a very good pizza, with a slightly sweet sauce and fancy-ish crust. It was sort of expensive, but there were delicious cookies involved for free.
A Late night cozy pizza joint, with alcohol? thats my idea of home.
This place is awesome. Five stars for any pizzeria that's big. I know the Yelp reviews are sort of all over the place, but I would definitely recommend giving Piehole a shot. The sauce is really good and herby not too much sauce like most places tend to go over board on. The crust is delish! Cracker-crisp. It's a little pricey, but it's totally 100% worth it!
Definately try Whiteparty!( Ranch sauce, chicken ,white mushrooms, garlic and mozzarella). it's simply the best!
Oh Pie Hole...how I wish I could love you more....
The idea of this place is great - an open late pizza and drink option right in the middle of bar-heavy Boystown. I mean, Pie Hole has the right idea - if you want these boys to come in for a slice, you better not slow up their drinking train. The atmosphere here is often wild and crazy (especially on the weekends and during the gay holidays: Pride and Market Days).
Yet, with all that being said, the pizza is just not good to me. Also, Pie Hole charges $4 a slice - for about that price I prefer Panino's down the street. I just hope I've finally learned my lesson and can avoid the Hole the next time I'm drinking in Boystown.
What a great place to come to after hitting the clubs in Boystown. The pizza is really good and they always seem to have different pizza slices to choose from. Being a vegetarian I have sometimes had to wait for a pizza to be made, but it usually does not take very long at all. The sauce they use is really good. Great atmosphere too! Perfect place to satisfy that hunger after a night out in Boystown!
sober review of pie hole, booyah!
my roommate and i were in the gayborhood looking at apartments when we stopped into pie hole for slices. the staff was super friendly, upsold some wine (nice work ladies!) and served our pepperoni slices quickly.
very thin crust, slightly charred, but totally delish. wine was nothing fancy but wasn't terribly pricey either. we sat on the cute little patio and people watched.
i'd recommend it to anyone wanting a quick slice in the hood!
Urg. Pie hole is closer to my apartment than any other food places, and yet I will not go there anymore. I have literally never waited less than 15 minutes for a slice of pizza. Sometimes I would even call ahead and then wait 15 minutes to leave, and I still end up waiting 5 minutes!!!!!! And the pizza is just not that good. The sauce is not very good, which is why I guess they have other options for sauces.
Really not worth the $5+ price tag for crummy pizza
I've only had pizza from this place one time, but it was pretty delicious. We had ordered the sausage and marshmallow pizza and it was much more than I expected - pretty darn good. The unique mix of the took actually work well together and make an explosion in your mouth, the good kind.
I'm disgusting and I like to watch TV while I eat. This is what makes Pie Hole great. I was able to eat my tasty goat cheese pizza and watch America's Next Top Model. They also have really cozy stools. I'm not a huge fan of the whole bar stool thing (I have long legs, but they aren't long enough to touch the ground), but these bar stools are made with seatbelts and they are so comfortable.
The place is quite small, but we were able to squeeze into some seats with no hassle.
I like this place equally for personality and pizza. The pizza is good - not the oh-my-god-orgasm-in-my-mouth-perfection-pizza that some may be looking for, but it is darn good and its deliciousness increases in relation to what hour at night it is and how drunk you are! Very interesting phenomenon, someone should make a graph.
The staff here are awesome, cool but not too cool for school...you know how sometimes it crosses over from being genuinely cool to that 'I'm trying to be cool, isn't it obvious how much cooler I am than you" attitude. But, I digress, this is about pizza.
Also, one of their delivery drivers is hot. I gave him a good tip.
go when you are drunk, otherwise I think it could be three stars.
THE place to hang out after-hours to get your grub on after a long night in boystown. Pizza is great, however, it's expensive to order a whole pizza. its $4 for a fairly large slice, and everything is made to order. Just a warning, it gets PACKED about 2ish. Be prepared to wait in line!
I live right around the corner from this place, so this is my new go-to when I need a piece of pizza.
The 2 fellas who work the counter (at least they have every time I've been there) are funny and engaging. They will offer up all kinds of different pizza options for you. I also really like the customized slices of pie - I just had Sausage and Mini Marshmallow last night, and it was dang tasty!
It is pricey, as noted in other reviews, but the slices are huge and if I'm gonna pay 5-6 bucks for dinner, I might as well get a kick ass piece of pizza. Definitely a must if you are strolling in the 'hood this summer!
This pizza is the best I have had in awhile! What makes it even better is the service, the owner personally delivered the pizza to my apt. and even stayed to chat awhile! Great food and service!
I never really remembered what this pizza tasted like due to the general level of intoxication that I usually was experiencing whilst downing a slice... that all changed about a week ago, and the pizza is actually really good! I had the vegetizza pizza and the ingredients were really fresh. We ordered delivery on Grubhub and the driver got here in no time! The driver ended up getting a pretty good tip too from us for his speedy and efficient delivery. Grubhub overestimated the delivery time so we were happy that it came a lot earlier.
I'm a big fan of Pushing Daisies so I didn't believe my friend when he asked if we wanted to go to the Pie Hole. It's a real place!!!! Such a big moment for me.
When we got there, they literally brought out a fresh pizza, half being spinach - my favorite. It's like they know me! The slices are very large and we took advantage of their outdoor seating to enjoy the mild night, although it did look like a party inside with a party light machine and a TV with some sports game on.
I thoroughly enjoyed my pizza slice and the cold beer. The guy and gal working were super friendly and totally chill.
Thumbs up! And now I expect fresh spinach pizza every time. You spoil me, Pie Hole.
Reviewed 03.15.98
Had a chance to venture out into Boystown on Saturday night. Went to Piehole. I thought the place was quaint, nice outside rainbow flag colored decorations for the store. Rather small inside. Not really meant for large amount of people, however -- but certainly does the business!
Didn't actually get the chance to eat there -- as we waited in line, the server, who happened to be deaf, but completed orders as quickly as he could -- suddenly pumped on the music and we were listening to blaring Hip-Hop. Not what I want top listen to when I'm eating (especially in a small restaurant).
As I said..didn't get a chance to eat the food, but it did look good..and fresh.
They need to just work on the music -- the server might be deaf -- but I'm certainly not. Hopefully next time I try this place, I'll be able to revise the review!
Bring back the white sauce! Ever since Pie Hole replaced their white sauce with ...gasp... ranch dressing (as a cost saving measure?), I've had less love for them. The idea of ranch dressing on a pizza is so completely repulsive. Yuck. And it means that their Chicken Piccatta pizza, which was so awesome, is no more.
But they still turn out a good pizza and they happen to be closest to home, which is why they still get our business. The Envy Pesto pizza is delish (when they don't burn it, which unfortunately happens more often than not), and the Angry Pesto is also a winner.
OMG what a great little place and I do mean little. You walk in and there is a counter where you order and it also has a few stools to sit down. The front window has a counter and stools and there are 4 small high tables to sit at as well.
The service was great. The guy behind the counter was super friendly, outgoing and fun. There was a stream of people coming in and he greeted every single one of them with a smile and all at the same time he was taking care of the customers at the counter and the tables.
The pizza...mmmmm, yummy. It defintely hit the spot to soak up some of the alcohol we had just consumed over a Sidetracks. The goat cheese sticks....to die for! I could've taken a bath in that goat cheese marinara sauce!
Piehole I will definitely be back!
My roommates are both lacto-into, so when I moved to this neighborhood, Pie Hole was pretty much my only pizza choice. Well, it's b/c they have this amazing Red Pesto pie, featuring goat cheese! So I ate Red Pesto every week for almost a year, and then started venturing into goat-cheese-compatible fixin's. Everything I've had here is great! Although sometimes they don't put enough (goat) cheese on, and it's a bit dry.
Oh, and... I rec this combo: goat cheese, bacon, mushrooms, french black olives (if you're feeling salty), fresh basil, fresh garlic
I realized that I probs ordered PieHole too often when the delivery boys started bringing me free soda. Although maybe my alternative forms of tipping had something to do with it. They always looked like they wanted to come in and have a beer with me, ya know? But I dig that in a pizza boy.
Ok, maybe I'm just REALLY picky, but I didn't think the pizza was all that great. I think it's the cheese...or maybe its the sauce...or maybe..its both.
I had it delivered and damn it was fast. He said 30 minutes, and it was here less time than that. I won't say it's "pricey", but it's not cheap. $2 for each topping seems a bit much, but then again inflation is a bitch and I have no clue what other places charge. It's not something I tend to look at.
And for what its worth, this is the first time I ever ordered a pizza and it wasn't round. it was more like oblong...not that it has anything to do with the taste. Just thought it was weird.
This place is really cute. Great decor and beautiful outdoor seating.
The pizza, on the other hand...not so great. They took it straight out of one of those revolving glass tray things and it tasted like it had been in there for a while. Not fresh, and the crust was dry. I did like that they didn't pile on the cheese like most other places, but I just wish the sauce had a little more flavor.
I've had much better thin crust than that for $5. And $.50 per topping? I don't like that at all.
Pizza was tasty, and I'd go back. It was a little overpriced and slightly overcooked, so that knocks off a star. The counter guys were really nice and very friendly. I loved that it's sort of a bar too. Would definitely come back, as this place just has a friendly, fun vibe.
My aunt shipped her car from Honolulu to Los Angeles and drove all the way to Chicago just for a slice of Pie Hole Pizza. That's how awesome this place is! Well... she was also moving to Atlanta but she just had to stop for Pie Hole!
I love Doug. He's very friendly and outgoing, great with all his customers. Great tip for ordering pizza at the Pie Hole... this is the place to go crazy with your toppings! Go for the unconventional and unleash your adventurous, enthusiastic spirit for original pie creations! Pie Hole encourages experimentation! You can't do that in most other pizza places.
Also, Pie Hole is technically outfitted as a bar or "thirst station" in the middle of Boystown so there are tons of drink options available with a fine selection of beers and wine! There are a couple tables but eating at the bar is fun.
Went back and just plain didn't like it. Pizza was just fair and the music was still too loud--yeah, I'm over 40. Come on guys: have some daily specials that involve the food and not based on how drunk I want to get. Pizza by the slice is always an overpriced deal, but for the price of three separate slices, you could get nearly a whole pizza.
Quite a classy little pizza stop on the way to or from the Halsted bars.
Brett's review is obviously more useful than mine, but I wanted to give Pie Hole a few more stars in its crown.
Love love love love love!
This place is awesome. Great selection of pizza and everything had just the right amount of sauce, cheese, spice or what-have-you.
The atmosphere is relaxed and comfortable. Very small and cozy. I first went here during the presidential debates and enjoyed my pizza while watching staff members cheer and jeer at the candidates like they were watching a football game. Hilarious, and memorable. This place has since been among my favorites.

