Headrest Barbershop

My friend recommended this spot to me as a place to get my head shaved. Mr. Jackson did an absolutely beautiful job! His service was incredibly friendly and funny and he knew exactly how to make my cut look amazing. I highly recommend Headrest, and I will definitely go back.

I had a 6 week hockey beard and my wife and I walked in. We were welcomed in by a very friendly staff. We didn’t have to wait very long. Jeff shaved me and did a great job.

Tanya owner of Beauty is my Biz is also located within Headrest Barbershop. She is the best! Tanya has a wonderful personality and is very professional, prompt and very customer focused. She specializes in natural hair care, whether you are wearing your natural hair or weave. Hair care is first and foremost with Tanya and she is very knowledgeable in explaining, your hair type, what is beneficial and what will promote strong and healthy hair. My natural hair is healthier than it has been in years and looks great. Tanya also does my sew-in’s and is able to style according to the pictures I bring in.

Walked in last minute to get my son his Easter haircut, and found our new barbershop! Jeff took care of us and was kind, prompt and professional. He made my son feel at ease, and most importantly gave a great haircut! My son would often complain his haircuts hurt when he went with his father, but not this one! It’s nice to find a great barber convenient and in the middle of downtown with good prices. I was also impressed that they served a diverse clientele with ease. We will definitely be back!

We stayed at the Congress and this was super convenient for a beard trim/​shave before a night out.
Prices are really reasonable (worth a lot more if you ask me) and the barbers all know what they are doing.
They take cash and card so no need to run to the ATM if you forgot cash.
Jason rocks, I highly recommend him if he’s working.

I got an excellent haircut in my stay in Chicago. My barber, Jose, was skilled, knowledgeable about his craft and made me feel welcome. The barbershop has that classic design with new technology and the rest of the staff all really enjoy their jobs. It’s easy to tell that they do by the way they talk to each other and crack jokes. If I’m ever back in Chicago, I’ll get my hair cut here.

I wish we could give half stars because this would be 4.5 star rating for sure!
As an avid Unilocaler, I always research the reviews to see what people think about the said business. Because I moved to a different part of town (Streeterville from Gold Coast) I needed to change barbers. The one I already had was spectacular but it was easy to just walk there and back home and now he is a little ways away. No further than Headrest actually, but I did have to try this shop as a last minute emergency since my previous barber had to cancel.
At any rate, after reading the reviews I decided to try out Headrest. And I am very glad that I did.
Location: this location is awesome! Right on South Michigan so it makes for prime people watching and great views! The huge floor to ceiling windows in the new location is awesome for just these reasons alone. Natural light never hurt anyone anyway right?!
Price: Spectacular. Even though they are about to raise the price 5 dollars for a standard cut, it is worth it. I was pleasantly surprised to receive a 20% off coupon for checking in on Unilocal,however. I saved a good 5 dollars off. Also they take cards! which is awesome!
Interior Décor: blast from the past! Very vintage very antique. I felt as if I transported back 4 decades when I stepped inside. My father would really love it here.
Service: all of the barbers are funny as ever. I was laughing the entire time during my cut. I have to admit though, It felt awesome to get a sort of celebrity treatment when I told them I was an Elite Unilocaler. But even before this they were awesome.
Cut: I received a cut from Raynie. I do believe he is either the manager or owner, at any rate… the guy is highly skilled. And should be a professional comedian. He is very personable. I mean, he literally hugged me instead of a handshake when we first met. You don’t get that. He is like that crazy uncle we all have. But in a good way. I had not had a haircut in a solid month. So my head was in real bad shape. Raynie conducted reconstructive surgery on my hair (as he called it). I looked like a completely different person on the way out. It was awesome.
I had to dock half a point though because in the middle of the cut he stopped to help one of the other barbers fix their broken chair. It wouldn’t have been an issue except the other barber was just standing there not doing anything to help Raynie so if it was a one person job they should have just let the other barber fix it by himself and not take 10 minutes out of my cut to fix his chair. My time is valuable you see.

Always festive, hilarious, urban and most importantly… great cuts! Located at south end of Congress Plaza Hotel… use street entrance to shop on Michigan Ave (not hotel lobby entrance).

My boyfriend got a great haircut. The shop was busy because it was NYE but the staff did everything to make sure we were taken care of while we waited. They had had a NYE celebration and offered us food and drink. Everyone was super friendly. If we ever move to Chicago he says this will definitely be the barber shop he will go to!

I moved to Chicago from Louisiana and was clueless on where I was going to get my haircuts. From a google search, I found Headrest, and it’s been great since. Jeff is my barber, and it’s always easy to get an appointment. Plus, the atmosphere is very professional, and it takes no time to get a superb haircut to continue with your day. I highly recommend Headrest for anyone looking to get a great cut, and I look forward to having Headrest as my barber spot for years to come.

Great shop my son and I get out hair cut there weekly. Staff is friendly and professional, and all the barbers can really cut any type of hair. I’d recommend this shop to all my friends.

An amazing barbershop! I love the atmosphere. I was really nervous to get my hair cut but the barber was kind and put me at ease. Ask for Raynie he is hilarious and very skilled! I will definitely be back! I’m in love with my haircut he gave me exactly what I asked for!

Jeff did a fantastic job cutting Jeans hair for a special event. He was quick and through and paid special attention to the line. The music was good and the atmosphere was welcoming!

I first stumbled upon Headrest Barbershop when I was on a quest for a barbershop that was located downtown. Being that I’m new to the city I didn’t know what to expect from a barbershop located downtown (i.e. overpriced, unskilled, etc.) but the majority of the Unilocal reviews that I read were positive.
From the very moment I walked into the door everyone, from the barbers to the clients, were extremely personable and friendly. The atmosphere will give you the impression of having been a customer for years even though it’s your first time visiting. The barbershop itself is small with roughly four waiting chairs and only three barber chairs.
I’ve had the fortunate luck of working with Raynie for the last couple of months that I’ve been going to Headrest. It is very hard to to find three equally skilled barbers that have great chemistry. Raynie is great because I’ve observed him countless times try to squeeze in a walk-​in client or come into the shop earlier to fit someone into his schedule.
In the past I’ve found it difficult to find a barbershop that was both aware and respectful of the clientele that they’re serving. But the barbers at Headrest Barbershop are great at tailoring the conversation to whomever is present, whether it’s a little kid getting their first haircut or a tourist visiting the city for the first time. The conversations are always lively and entertaining.
I would highly recommend trying out Headrest Barbershop because you will never want to go to another place. If you do try out Headrest ask any of the barbers about stepping and the importance of knowing how to step.

One of the best barber shop in Chicago. In side of the congress plaza hotel go check out Raynie he will have you shape. He gave me my hair line back.

Stayed at the Congress Hotel for a weekend getaway. The lone bright spot was this Barbershop. Came in from Cleveland for a little R&R. Got my cut from Jeff. He did me right. He took time with my cut and even gave me some services for free just because I was knew. The atmosphere was just like home. Good music, good conversation. I appreciate him and his staff for making me feel at home with the cut. I’ve now found my Chi-​town barber. Worth every penny!

Great service! Barbers are very personable. If you are new to the city I would definitely recommend.

I’ve been floating between haircutters for the past two years and the hunt is finally over. Walked in and Manny cut my hair… he’s excellent at his craft. Honestly, he was better than my old haircutter (Halo) and less expensive to boot. A lot of urban men’s salons charge crazy hight prices compared to what I was used to growing up ($ 55+ compared to the good old $ 12 – 15 haircuts of my childhood)…but this place was easily worth $ 20-​$ 30 (depending on what they’re doing to your mane).
Won’t be going anywhere else. The shop itself is barebones, but I don’t think getting my haircut in a modern, hardwood floored men’s salon with a free coke and handwax were worth an extra $ 30 I’d pay atvother places… this place has skilled barbers at reasonable prices and a convenient location on the Magnificent Mile near South Loop. Go. Ask for Manny. You won’t be disappointed.

Very poor organizational skills for a small shop, I made an appointment few days prior to actual appointment through Whittl and I had a very tight schedule that day.
When I got there on time, someone told me I have to walk 3 blocks as the guy who is suppose to do you hair went to our other place, I got frustrated and asked one of the available guys to do it instead, 5 of them refused for unreasonable reasons with no interest in solving the problem their colleague has caused.
I cancelled and will never go back!

Great old school barbershop inside the Congress Hotel, ask for Manny. Only $ 5 for a beard trim for great for gentleman like myself who need a bi-​monthly beard trim from a skilled professional.