I came here for a back to school haircut for my 6yr old. This was his first time at a barber shop we always went to a kids haircut place. Let me start with how very welcoming Jesse is. He made my very shy guy feel so confortable and confident. He treated him like one of the guys and my son loved it. Now to the important part the hair cut. My son looked so sharp. He gave him the haircut I wanted and it looked so clean and sharp. We will be back again especially since my 6yr old can't stop talking about Jesse. Very friendly and clean place. read more

Easy to schedule. Jesse is friendly and knows what he is about and what he is offering. I like the online reservation system and I respect the cash only stance. read more

Jesse gives a good haircut with a fun conversation. He knows his customers. Appointment only, and he is always promptly on time.

Today was my first time visiting Jesse's shop. Making the appointment was easy and the final result was fantastic. I had a great time chatting and walked out looking and feeling good. I had a long time barber who recently moved away and I just found where I'll be going from now on. Thanks Jesse! read more

I just got my first haircut in over a year. Jesse gave me exactly what I needed but couldn't vocalize - making the most out of what hair my balding head still produces. read more

Awesome spot. All the barbers are great there. Personally, I like going with Jesse and Rhett. They do Online and over the phone appointments so you don't have to wait and they are always on schedule with your time slot. Don't do a no-show or you will be charged the haircut which is how it should be. Overall a great spot with nice hip haircuts from great guys. Definitely recommend. read more

Easy online scheduling and fair price. I see Rhett and he is great! My only feedback is I wish they had later hours but hey, they deserve an evening life too! I used to go to Portage Gentleman Shop further west down Irving Park road but the turnover in barbers, inconsistency with cuts and general vibe of frustration from the owner brought me here. read more

I want to like this place because of the old school feel but I feel like Im paying too much. Kids haircuts start at $22+ I think thats way too expensive for a kids cut I went once spent $30 with tip. Decent trim for the kid but the price way too expensive. Best of luck to them... read more

Jesse is one of the best guys I know. I met him a couple years back when I randomly chose him as my barber for my first appointment at The Belmont Barbershop. Best decision ever. Now that he has his own shop, he's running it the way he feels he should which is great customer service and quality haircuts as his top priorities. Aside from Jesse, I don't trust anyone with my hair. He really knows how to cut hair, especially the classic gentleman's cut that has blown up as of lately. The shop is very clean with an awesome vintage feel. It's what a true barbershop should be. Call in and set up an appointment for a cut. You will not be disappointed. read more

Jesse's Barbershop - Barbers Near Me - Chicago, Illinois

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Jessie and Rhett are professionals at cutting hair. I have had great experiences everytime I have ever received a haircut and have been patronizing the business since they have opened. They are punctual and take their time to listen to what you want done to your hair. I would highly recommend them. read more

Very cool shop. Both Jesse and Rhett give a great cut. Prices are pretty reasonable, but the cut that you get is good. They talk to you about what you're looking for, and they have an understanding of their craft - so they deliver what you want! They accept reservations through the Resurva app. Parking (paid) right out front. Far superior to other shops in the area (and I have tried most of them). read more

Nice place with two barbers. It's clean with a convenient location and offers affordable cuts.

I've been coming to Jesse's for years. I don't often get my haircut but when I do, I always come here. Jesse knows hair and knows what is best for it and what will look best for the shape of your head. I've never gotten my haircut by Rhett but friends have said he does well also. The ambiance of the venue has that older feel and it's a really nice place to get your hair cut. It is cash only, but that is not a big deal as there is a bank across the street if you forget. Overall I've gotten my best haircuts from him and will always be coming back. read more

My little guy is turning 6 this week. SIX!!! And although I have liked the kids hair salon places we have used, I wanted to find a place that was more convenient. And also less baby/kid themed. Because we are moving out of that stage and honestly, less crying kids the better. We were able to get a same-day appointment at Jesse's online. Their booking system is easy and they stuck pretty close to schedule. Rhett was the barber who took care of my son and this was honestly the BEST haircut he's ever had. He has this tuft of hair in the back that has been hard to style. I showed Rhett the type of cut I wanted and pointed out the troublesome area. The cut worked so well. I am truly amazed. The cut took about 20 minutes...could have been less, but my son likes to squirm and giggle when the razor buzzes near his ears. Rhett was super patient when my son got the giggles too. Both Rhett and Jesse are very friendly and professional. I'm sure they are used to hovering moms who bring their little guys in. They bantered with customers (who seemed like regulars). It's definitely a great neighborhood business that I plan to keep taking my son to for hair upkeep. read more

I've been going to Rhett for somewhere around 5 years now. He gives a perfect haircut, atleast that's what everyone else tells me. I had Jesse cut my hair when I was in a bind and Rhett wasn't available and he did an equally impressive job. They are both experts in their craft and I highly recommend booking an appointment with them on Booksy. read more

Jesse is not only one of Chicago's best barbers but a man who takes just as much pride in his shop as he does his neighborhood. Portage Park is blessed to have him. A positive business owner who is not only passionate about the area but is actively involved and lives in the community. Jesse was essentially raised in the barber shop. At the very young age of 4 he was already sweeping floors at Hairy Pete's. By the time he was 9, he was awarded the coveted 'Let Your Soul Glo' internship. A prodigy by 11, he was not only the Midwests youngest Master Barber but had the highest grossing chair in North America. After many years of global lime light, being the personal barber for dozens of A-List celebrities, Athletes, high ranking Politicians and Dignitaries. Jesse walked away from it all and disappeared into the mountains of Mexico. After a 12 year sabbatical, Jesse has quietly resurfaced where it all began for him. Portage Park. If you are lucky enough to land an appointment at Jesse's Barbershop, MAKE IT. He will have an ice cold Old Style waiting for you and tell you stories that belong in Hollywood scripts. He is worth the wait, he will make your hair look great, your friends will hate, even if your overweight you will start to date, remember to tip or he will blacklist you throughout the state. Book online and SHOW UP ON TIME! read more

I've gotten my hair cut by Jesse for a couple years when he had a chair at the Belmont Barbershop, but now that he's opened his own place I had to try it out. It's a beautiful shop with an old-school, 1940's look and feel. Excellent (free) coffee, the same amazing haircut I've come to expect from Jesse over the years. Prices are better than at Belmont, which is a nice bonus. He does straight-razor shaves too, which is a really cool experience if you've never had one. Lots easier to park too... there are some metered spots but if you park on a side street it's easy to park for free. Really excited to see Jesse with his own barbershop. It's an excellent addition to the *real* 6 Corners neighborhood (Irving Park and Cicero Ave). read more

Like many of the reviewers, I first started getting my haircut from Jesse at Belmont Barbershop. When I first started going to Belmont, I got my haircut by practically every person, just to see who I liked the best. That person ended up being Jesse. This is not to say that Jesse is "better" than everyone there, I always got a very good haircut from each person. I think that finding the right barber is more of a "I know it when I see it" approach. That's how I feel about my haircuts from Jesse. I have a high and tight with a side part, and it's exactly how I like it. Here are some pluses about the new shop: -Appointments are easier to get. At Belmont, I feel like you need about a week of lead time for Friday or Saturday appointments, so if you forget, you will be stuck with a ragged cut for an extra week. At Jesse's, I don't think I've ever had an issue calling a couple days in advance. -Appointments are a half hour. At Belmont, appointments are 20 minutes. Big difference. Plus Belmont was very busy. And if someone is late (which happens all the time, make it to appointments on time fellas), the whole system is thrown off, which is frustrating for barbers and customers alike. At Jesse's, the process is more relaxed, and Jesse has plenty of time to get all of the details right. -$15 for a haircut, great deal. I will end with a story about what a good guy Jesse is. He was cutting my hair one day at Belmont, and a guy walked in with a long beard. The guy said that he was going on his first job interview in a long while, and he asked if he could get a beard trim. The issue was that the guy only had a couple bucks; the guy wasn't unhygenic, he just was strapped for cash. The person who was working the walk in chair said no (which was completely his prerogative, and I would have probably done the same). Jesse told the guy to hang tight for ten minutes, he would trim his beard on his break. So support a solid guy who gives a great haircut. read more

Love this place. They are no nonsense, price is reasonable. They give a great haircut. It's clean inside with cool old school decor. Has an old school vibe, which I really like. Jesse is awesome. Knows what he's doing. Will keep going there. read more

Rhett and Jesse provide top notch cuts for even the most unruly hair. They come across very friendly and care-free, but they are meticulous professionals when cutting your hair. Before going to Jesse's, I have wasted countless minutes and dollars on haircuts on the Northside (incl expensive beard-wearing, fancy talking barbers from Logan square) that show their flaws as soon as I get out of the shower. At one point, I was in a bind and used my buddy's expensive barber for my pre interview haircut and it was awful! I called Rhett and he squeezed me in, and fixed my haircut within an hour. I got the job and I'm certain the clean and professional cut made a difference! These guys are the best barbers at their craft and customers can always count on some great conversation and hospitality. Jesse's is the best. You can reserve online, too. I hope this helps others with unruly and difficult to cut/ style hair! read more

Jesse is not a stylist or a hairdresser; he is a barber. Jesse knows how men's (and boys') hair should be cut. There might be hair on the floor when you walk in, just as there may be sawdust or welding fumes when you walk into any other workshop. Jesse is a skilled tradesman, and his trade is to make sure your mug is framed and groomed in the best way possible (or, I guess, however you ask him to). Anyone who's seen a terrible tattoo knows the difference between cheap and a good deal. Sure, you could go to the $5 chop shops all over the city. You could just as easily go get inked by some scratcher needling you in his mom's basement. But those who care want quality work, and to get the professional quality work that Jesse does (for only ten bucks more) is a great deal. Plus, he's a local guy running a small business in the community. Call ahead. Bring cash. You'll be glad to have found your new barber. read more

More Dont's than Do's... They Don't answer Their phones, they Don't encourage you to leave a message, they Don't return your call after leaving a message, they Don't allow walk in Business, they Don't take Credit Cards, they Don't value their clients... They Do give a good haircut if you can make an appointment, they Do charge a lot of money for what they Don't offer! read more

If I could give this guy a political slogan, it would be "Make me look great again". I have not been let down once with this guy. Yesterday he gave me the best haircut I have ever had in my life. And you know what? After he was finished, I never would have thought to comb it the way that he did. It looks absolutely fantastic. Also, cool to speak with, and can tell when you've had a long day at work and would rather just sit there quietly. Sticks to his schedule, yet gives a quality haircut. Just make sure to bring cash, he doesn't take credit card. To top it off, the vintage decor makes you feel like you're back in the good 'ol days, getting your haircut before seeing "The Pride of the Yankees" at the movie theater (Although he's a Cub fan). Good barbers are hard to find, but Jesse's Barbershop is second to none. read more

I rarely ever write reviews but I had to after this visit. I've heard about Jesse from a few friends and I really needed a new barber after my last haircut. TIP: DO NOT EVER GO TO A $5 Barber. There is a reason why they only charge $5. That's my warning. But I got lucky, I called a few hours before and got an spot for a haircut later that day. I walk in a little early and Jesse was more than happy to see me early since he had no one before me. I explain what I wanted and he knew right away that someone messed up my hair bad last time I got a haircut, but he did his magic and I walked out with an amazing haircut. Simple as that. Both barbers were awesome to talk to and price was completely reasonable. Hard to find a great barber like this for only $15. So bottom line is that these guys know what they are doing and both seem like they love their profession so you get this sense of security that they aren't going to mess up your hair haha. But thanks again Jesse. Also Cash only. read more

Jesse and Rhett run a great shop. My son and I have been customers since they opened a few years ago and it is, honestly, one of the best barber shops I've been to in the city. They are extremely friendly and professional and are great barbers. Every time we come home and my wife sees my son, she raves about how great he looks (and I guess she doesn't mind my haircut too much either ... ;) These guys are great. The shop is clean with a 1930s-ish motif that reminds me of the barber I went to when I was a kid out in the 'burbs. And, the fact that they make available coffee/beer/bourbon for free to those who wish to partake is an extra added bonus. I find their prices quite reasonable, but when you are surrounded by fade shops offering $5 mass-produced trims, I guess their prices might be a bit high to people coming from shops like those. I've never felt they are expensive though. Portage Park is lucky to have Jesse's Barbershop in the neighborhood! read more

I have found my barber. From the checkered floor to the older barber chairs everything about this place is awesome. I can honestly say, without hesitation that I just received the best hair cut I've ever had. I will be a regular. read more

Jesse's Barbershop is a great addition to the Portage Park/Old Irving Park area. I have to admit that I am not very loyal historically to those entrusted. I don't know why either. I'm 100% sold on Jesse's Barbershop. 1. It's a very well run business. Call and make an appointment or sit your butt down and wait your turn. 2. Simple & Cool. It's a pure barber shop where there's no gimmick. Want a cut? Come on in. Also, Jesse & Rhett are chill barbers. There's no obligation for small talk but they're both pretty cool guys so don't be a chump and talk. Once before, when at the Lyric Opera House Barbershop, did I get a similar experience. Advantage Jesse's as the best cut so far for me in the city. Schedule an appointment and say goodbye to having to listen to some mom bicker with her seven year old at Great Clips. read more

First time here. Jessie and his barber were nice guys. Jessie gave me a great cut and was nice chatting with.

I first found out about Jesse's Barbershop through Facebook updates from our alderman and others. Enjoying articles by Brett McKay, about men returning to old fashioned barbershops, I decided to do just that. I am so pleased to call myself a loyal customer from the first visit! Jesse and Rhett are welcoming and friendly to all, and they know how to give great haircuts for men! I have had each of them cut my hair, and both do a fantastic job! I also have witnessed them giving haircuts to small boys, and I have to say, they are just as great with them! Some barbers and stylists out there don't have the patience or skill to work with little kids, but these guys are great! One of these days, I'm going to get one of their classic, hot towel, straight razor shaves, too! Haircuts are $20. Shaves are $30. Appointments taken on Resurva.com read more

Great local barbershop for any guy in Irving Park/Portage Park area. Professional, friendly and great customer service. I've gone to Rhett for about a year. He always does great work. The straight edge neck shave alone is worth the trip. read more

I've been a loyal customer at the barbershop always Welcoming and Relaxing. Always have great conversations with Jesse and Rhett two solid stand up guys. read more

No DEBIT or CREDIT Cards? Get WITH the MODERN Times. Alcohol (Bourbon) on full display in front of small children. The bourbon was on the bottom shelf of a table next to bench seating. I received a poor pompadour comb-over style haircut that was not how I requested my hair to look (with texture and for fine hair). It didn't match my face, and it was done like a little boy or some hipster doofus would have it done. Other places nearby cost a lot less and do better cuts. read more

i followed jesse from his old shop he was at forever! jesse's barbershop is located at six corners in Chicago and it takes you back in time. always great service from jesse and rhet! highly recommended for a shave or a haircut in Chicago and when you're there, get some Iron Heritage pomade as well!!!! read more

I've been going to Jesse for almost 7 years. Even though I've moved to the south side it is still worth the trip for numerous reasons. He is a master of his trade and the quality of his cuts are second to none. I've switched up the style a few times and he is always accommodating. I've sent numerous friends to him and have even brought my pops in for a solid old school cut. Jesse is the best around and if you're looking for a solid haircut this is the place. read more

"The Best Barbershop in the city..." I really can't say enough great things about Jesse's Barbershop. Jesse is a phenomenal barber that runs a great shop. He is super talented, friendly, accommodating, and very professional. I have been with Jesse since his Belmont Barbershop days and I leave time and time again as a satisfied customer. It's a shame there is some bad seeds out there who put out feedback that just doesn't make sense. read more

Both Jesse and Rhett are fantastic barbers and friendly people. I wouldn't go anywhere else for my haircut, period. As long as you bring cash with you, set up an appointment, and show up on time, you will always be treated with the utmost respect from them both. I've been going to Jesse's since it opened and I will continue to go there until I move out of Chicago. read more

Jesse and his staff are terrific barbers! Great haircuts at reasonable prices in a fun atmosphere! They do beards too!

I was a customer of Jesses back when he was at Belmont Barbershop and have made the switch to his shop since he is the man. This place is the real deal. This is a real barber shop . Great hair cuts, no frills, and authentic. Warning I would not recommend Jesse to Hot Yoga enthusiasts, this place is for real dudes. read more

I passed this place up a couple of times while driving and I always liked how the old skool barber shops looked so I made it a point to check it out. When it was time for some grooming I went and made a visit and was greeted right away and there was an open chair. Rhett (the barber who attended me) took me right away. Everything was going ok until his appointment came in (which I had no prior knowledge of) and he told them he would be right with them. I felt right away that I was going to get cheated of a good hair cut and beard trim/ shave. Basically, he tells me that he wont be able to fully take care of me and unapologeticly. But, I needed to finish my beard so I was willing to make it work with him and come back later, gave him a $20 (thinking that I was paid in full) and left. 2 hours later I came back told him that I would like my hair line to be tightened up in the front. He said he can't do it and wasn't trained on it. Im thinking like really?? So "im like alright, ED Debevics of hair here." So, I'm trying to talk him into it but no budging so I stopped asking and just wanted it to be over with. Finally done, I gave him another $5 bucks and he said was it was $25 bucks more! I only brought 25 bucks because I figured that covered the cut and the tip! So he immediately goes off, saying "I don't go to your job and expect it to be free!!" I tell him I can comeback tomorrow to pay the rest and he's still upset so finally he was like "ok" assuming I would I never come back, and I left. I'n my car now, like damn that was an expensive cut. But i'm not a dead beat so I'm gonna come back and pay what I owe. Then I had remorse about doing that because of how rude he was and called the barbershop and told Jesse the owner I won't pay the rest because I was treated rudely by Rhett. He was apologetic for the misunderstanding and listened to my complaints so I figured Ill comeback and payup because he was being respectful and I just don't like owing people money. I came back the next day and Jesse said it was ok on the rest and gave me his card if I ever want to comeback to make an appointment. Moral of the story don't assume anything! 1. First time customer YOU the barber need to go over the prices before you perform a cut to protect yourself for something like this to happen, not everybody is like me and will comeback to pay. 2. Don't kick somebody out of a chair while your still cutting their hair. 3. Don't jump to crazy conclusions about people. So after all this you would think I would give a negative 5 if I could right? I'm not like that. Despite all that I did get a decent hair cut. I like the way their clippers make my hair feel. The place looks awesome and It provides of a more adult like atmosphere. If you don't mind paying the extra bucks to avoid the rap tunes and the famous hair charts in most barbershop, this is the place for you. They do more when it comes to shaves like I guess what a lot barber shops did back in the day that was standard but now it's like "extra. " To be honest I've gotten the same type of cut at other barbershop considerably cheaper but like I said, Jesse's, in my opinion is considered more of an upscale shop to what most people are use to paying. I would also recommend to go see Jesse unless you like cocky jerks go see Rhett read more

Best barbershop on the northside. Jesse keeps it real and doesn't try to sell you homemade hair products like other local shops. Very easy to book appointments online. I have referred several people here and will continue to do so! read more