As a patron of Headrest for approximately 6 years, I can confidently say that you won’t find a better black owned and operated barbershop in the downtown area.I’ve gotten my haircut from 4 different barbers in this one shop, however, over the past 3 years I’ve been getting serviced by Antonio.Antonio is one of the most talented barbers in the city and definitely one of the best to ever get his hands on my head. He’s very personable and makes everyone feel comfortable. Each time I get a cut, I feel “commercial ready!”Headrest is an experience. You can never really prepare for it because there are so many different types of personalities behind the chairs.Fair warning: it is always packed here and almost all of the barbers have appointments. You should really anticipate spending an hour and a half (minimum) here even if you have an appointment.The wait isn’t too unbearable! The playlists are always it or you’ll get a complimentary front row seat to an impromptu stand-up comedy show! Yes, they’re all that funny!

I wish I could give ZERO stars, the african-american girl who gave me a haircut doesnt know a thing about proportion and symmetry in hairstyling. I paid 60$ for a mens haircut and she doesnt know how to use scissors, its clippers from the start to finish (what kind of barber doesnt know how to use scissors). I told her to trim the top and its so uneven I had to buy a hat to hide my haircut. I will never go back to this place. TOO EXPENSIVE & NOT WORTH IT if you still had to go, DONT GET YOUR HAIRCUT FROM THE GIRL.

I have been going there for 2 years. Raynie the owner is an artist with hair. Its an old barber shop feel with a funky vibe. The music when Im there is 70s& 80s which I love. Kudos to Headrest barbershop.

Having a day off in Chicago from touring and a haircut was needed.Badass service from the barber Eduardo, thank you hermano! Very nice place!

I got a great haircut here with Jose. The experience was amazing. It felt therapeutic getting my haircut abs my beard trim. It’s like getting your nails done but for men

This is such a great place. When you walk in, it feels so warm and welcoming. Everyone is friendly and safety precautions are taken seriously.

The shop was recommended to me by my colleague. My hair seemed so dry and decided I wanted a wash and blowout. I ended up having some waxing and getting a special conditioning treatment. Everyone in the shop is helpful and welcoming and knew their business. I will go back again soon and recommend them to others!

Nice and clean barbershop with friendly staff

Antonio is the best barber. Very cool, laid back dude that enjoys life. Some of the other barbers are so uptight and sensitive.

Great prices, clean environment! The owner did an AMAZING job on my sons hair. He really took his time, was so kind with him. GREAT SERVICE!

Great Hair Dresser 😉 My son loved Eddy who was An Extremely Patient and Lovingly Man towards children. Thank you Eddy

I always get my hair cut. The best! I’ll never go to anyone else. Thanks!

Amber is very nice and friendly- great price, hair feels great

Clean place with lots of friendly and skilled barbers.

Love the atmosphere, My Stylists is Great with Communication and knowledgeable of her craft, I Love my Sisterlocks, Thank You for a new me

Great service. Highly recommended.

I called this place for a hair cut and some guy answered and we both agreed on a time. I showed up and when I was escorted to his station he was doing nothing but seating on his phone and told me he forgot he had another appointment that he was waiting on and asked me to go back in an hour. So I ended up going elsewhere. Second time I got to try them someone else answered the phone and when I got there the stylist was rushing with my cut. And honestly did not look that good. The staff at the entrance was also no very friendly. The place is not welcoming for a new client and they are not very professional. Not to mention the place is a mess and the station I was in was also a mess. Will never go back

Great environment loved the felling of the family fellowship!

Tonio is a great barber. I highly recommend him.

Always a great experience!!

Wonderful fun experience and excellent Barbers.

Headrest has it all figured out. I sat with Tim, not even knowing what I wanted to do, and he provided me the best haircut I’ve ever gotten.Their barbers are committed to providing top notch customer service and it really shows. Best cuts in Chicago!!

Terrible service I repeat terrible service!!! I came to town for my daughter basic training graduation. The barber seemed very friendly, I guess he was sizing me up. I told him I was from out of state that’s when he figured he could RIP me off. I asked him prior to getting my haircut the price Eric stated 35 dollars. That’s was kinda of pricey however I agreed. So when he finished I asked him for change for forty and he stated to me your haircut cost 40 dollars. Bad buisness will never go back!!! On top of that he wasn’t even a good barber. This is terrible and the owner should fire him that is a direct representation of him as well.

Tim was great! Cleaned me up like only a true Barber can! Great old school shop that has stayed with the times. Highly recommend!

This barbershop is outstanding.. Great atmosphere.. Great location but most importantly great barbers. Jeff Smith hooked me up. He was great but his fellow barbers are outstanding as well. Next time I am in CHI-Town I will be back. If you in CHICAGO and need a cut.. GO there

I have been coming here for a year or so now, and I can say from personal experience that all of the barbers are equally meticulous and friendly. I have a couple guys that I usually request out of habit (Jason and Manny) but honestly, you will be equally impressed with everyone. They all ask you exactly what you want, check with you as the cut progresses, and do detailed work. The price is great too. Its quite simply just a cool, friendly neighbourhood place that I look forward to visiting every few weeks. After trying at least 10 barbers since I moved to Chicago, I wouldnt go anywhere else. Its official.Side note: I also have a hilarious memory of the shop (back when they were located right in the middle of the congress hotel lobby, as opposed to on the corner with their own entrance) when a gay leather convention was happening in the hotel, and every barber working that day was curious and totally fun about it. No homophobia at all. So if youre a gay man like me, you wont have a problem here either. Cheers guys!

Look at the blade marks! I noticed it after I came back home. The response of the staff is rude. Even though they charge a lot of money, their service is bad. I will never visit this barber salon.

I am from Chicago but now live in Springfield IL. It’s been some years since I’ve gotten a haircut in Chicago. I am also very particular with who cuts my hair. Not only is this one of the best barbershops I’ve been to in Chicago, but also amongst the 11 other states and several towns that I’ve lived in. It is very professional with a friendly environment. The barber that took care of me was Tim. Tim was friendly and professional and gave me the best haircut that I’ve gotten in years, even informing me of some tips for future hair care. My only regret is that I couldn’t take Tim with me back to Springfield. I’d recommend this shop and the Barber Tim to anyone and everyone. A must stop if you’re in the downtown Chicago area and need a fresh cut.

As a tourist I wanted an authentic barber shop type experience, basically like in Coming to America. This place not only is a great barbers, but is so authentic its great! Played chess, chatted politics, talked coffee, listened to music, talked about the 80s, oh, and also got a great haircut. Very popular but if you arent rushed, a quintessential experience for me in my USA trip. No expensive either and they clean shoes too!

My sons team was in Chicago for a tournament and he and a team mate got their hair cut at Headrest. Randy made us all feel so welcome and entertained, and he came to see them play the next day. A highlight of our trip, and what a great ambassador for Chicago!!! Oh, and fabulous hair cuts!!!

There was some miss communication about mg appointment. When I got there they didnt have me in the books. They jumped back from that. They asked me so have a seat and someone will be right with me. Jeff was amazing barber gave me a a sincere greeting played some great music, had some great laughs, each Barber has their own unique personality that gives the shop an outstanding atmosphere Im from place to be in

Wow!! I am Wowed!! Wish I could give more than a 5 star rating. Im new to Chicago and needed to get a haircut. Saw the reviews on here and decided to check it out. Its beyond amazing. I didnt have an appointment and walked in. I was attended to almost immediately. The guys were so funny I laughed the whole time there. Very funny and lovely people to be with while cutting your hair. Wish I was able to cut my hair everyday.

Im from St. Louis and I was looking for a barbershop. I went to to like three other barbershop and i didnt like any of them. But once I went to headrest it was the best one. I think Jeff is the best barber in the Chicago area. I highly recommend them!

Manny and Jeff were working when I called and asked if I could stop in. Walked over and had me in a seat talking bulls*** just like you expect at a barber shop. Im from out of town and felt like I had been there hundreds of times and was a regular. Manny was quick with the cut but didnt skimp on quality as I was very pleased with the end result. Will return if I am in Chicago again and need a cut.Manny for Mayor!!!

Very classy place. Best barber shop in town. Ask for Tim, hell get you right.

Been a few times, they do some good work but the policies are kinda ridiculous and certain barbers have weird schedules. Can’t tell if it’s laid back or weirdly professional. If you are trying to get to Jose, be warned that he is practically unattainable. ALSO PSA it’ll be double the price if you’re late at all so I’d say this place may only be for the punctual lol. The way they run things are fairly questionable but hey, a fade is a fade yeah?

Very personable and professional. You just feel comfortable. They even offered us a cold drink while we were waiting.

Best Barber shop in chicago wonderful atmosphere great conversation also with a awesome view of michigan ave. I love the old school wood work decor and just the overall look of the establishment, the entire staff is friendly and caters to all your needs. Id definitely recommend this shop to everyone and continue to keep coming back myself.

Grew my hair out with no idea what to do with it. Went past this one a few times downtown and decided to try it. Made an appointment and Jose picked it up. Once he saw my hair he started giving me ideas, we decided on a cut, and its great. Its a nice hood type barbershop in the heart of downtown, check it out.

Convenient location to downtown and south loop. Great for travelers!

Worst service Ive ever had in a babershop.The person I spoke over the phone with, told me to go at 3 pm, was there at 3 o clock sharp, and the gentle men just told me to sit down and enjoy my coffee while he was finishing with a lady. Then I showed him a photo of how a I would like my cut. Then the guy said, I got you. This guy doesnt has the slightest idea of how to use an electric razor, cut me on both sides of my neck, and didnt even bother to apologize about it. I would never return to this place and would not recomend this place to anyone.

If you are ever in Chicago check out HEAD REST BARBER BEAUTY SALON. You wont be disappointed. Fast and friendly service. 520 S. Michigan Ave.

My experience at Headrest was great! The service was amazing and made me feel comfortable instantly. It goes without saying that my haircut was amazing.

I saw some amazing reviews online before I came here but I was still a little skeptical. Raynie Jackson is hands down the funniest barber Ive met in my life. Great hair cut, great experience

Did a great job! ask for jim he will do great!!

Great staff! Love the hairstylist and the barbers are great!

Hard to find an urban barbershop in such a premium location. These dudes are NICE with the clippers (esp Jose & Manny). I try hit the spot every time Im working downtown.

Very friendly atmosphere. Sit down and chill out. Ask for Jose .

Great staff, great atmosphere, great conversation, great haircut! You found yourself a new regular

Great atmosphere great location. Maria was very polite and skilled barber recommend this shop

Manny and Jose are the best barbers imo. Ive been to many shops and they are the best.

Great place to get a cut in the south loop area.

Best Barbershop in the City! Ask for Tim

Friendly. Comfortable. Barbers of all kinds and skillz. Chess while you wait. Solid joint.

Robert is the only barber worth going to. Best barber!

A very good throwback to the way things used to be and its prime location could and should make it Chicago landmark. Thank you.

Skilled barbers and great environment

Great hair cuts, reasonably priced. Good atmosphere.

Hands down one of the barbershops in Chicago. Jeff did an awesome job and I highly recommend him and this place for your cuts.

Definitely very professional and fun shop! The staff is chill and its a good experience.

Great place great cuts great people

Just THE place for guys young and old boys and man. And just the most awesome skilled and interesting and friendly barbers!!!!

Great service

Dopest barbershop Ive ever been too!!Im a Hard critic when it comes to my hair but Jose is the man. I would have to say Ive been to alot of Barbershops in my life from NY, Philly, SC, FL. (list goes on) but Headrest Barbershop has the dopest atmosphere Ive ever been to. Completely comfortable environment and a quality cut while seeing the backdrop of the city.Absolutely loved the experience and will definitely go back if and when I come back to Chicago! Thanks Guys and Thanks José 👍

Simply amazing, high quality and extremely professional.

A very nice barbershop with great staff.

Really good. Im from Cali and I think I have to fly back to Chicago just for a haircut⭐️⭐️⭐️⭐️⭐️

To high for me

Polite barbers and very clean!!!

Great people, great cuts and a prime location.

Went in today and got a quality cut!!! Great experience

Great place! Tim was dope!

Good place for a haircut

Best place for cuts

Smooth Energy great people skills

Great haircut and entertaining conversation.

Great

Got to meet coach Chris Carr and (former NBA player)

Friendly staff only reason it gets two stars.

Manny is the best 😀

It was great!

Good stuff

👍🏾👍🏾👍🏾

Best value bargain shop Ive been to. Its better to call and make a reservation. You can use both cash and cards.