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    Esquire Barbershop

    4.5 (148 reviews)
    InexpensiveBarbers
    Closed 8:00 am - 8:00 pm

    By appointment only

    Updated 1 month ago

    Services - Esquire Barbershop

    Haircut

    Haircut and shave

    Shave only

    Esquire Barbershop Photos

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    Recommended Reviews - Esquire Barbershop

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    This is the best barbershop in the city. I've been going here for 8 years now and will go no where else. Aaron and gang give the best fades and are knowledgeable about their craft. As for the recent (small) increase in prices: They are AFFORDABLE for what you are getting. This isn't Sport Clips or even Floyd's for that matter. Here, they actually know how to use clippers and straight razors. Everyone else's wages go up to account for inflation. Why should it be any different for people in the service industry? People spend an extra $10 on far worse... There is a reason why I am a loyal customer. These guys reign supreme!

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    17 days ago

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    7 months ago

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    1 year ago

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    2 years ago

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    2 years ago

    I've had multiple cuts here and I've never looked sharper. My boys all go here. They keep it cool and you're in and out

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    1 year ago

    Received an awesome haircut from Wallace, would highly recommend their services. Left very satisfied.

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    4 years ago

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    2 years ago

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    4 years ago

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    5 years ago

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    6 years ago

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    6 years ago

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    2 years ago

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    4 years ago

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    2 years ago

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    4 years ago

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    5 years ago

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    6 years ago

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    4 years ago

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    7 years ago

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    7 years ago

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    5 years ago

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    5 years ago

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    5 years ago

    I've been going to Kaila for 3 years and I've never been disappointed. I drive about an hour for my appointments and its always worth it.

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    3 years ago

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    3 years ago

    This was my first time at Esquire. Jay was fantastic and gave me a great haircut! Will definitely return for future haircuts!

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    7 years ago

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    17 years ago

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    12 years ago

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    6 years ago

    A very nice experience. The barber was knowledgeable and the shop followed all COVID guidelines, all said I got a pretty good haircut

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    19 years ago

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    6 years ago

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    8 years ago

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    8 years ago

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    5 years ago

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    12 years ago

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    4 years ago

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    4 years ago

    Amazing haircut every time! My barber for over 3 years! Amazing and welcoming people.

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    4 years ago

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    Page 1 of 4

    Ask the Community - Esquire Barbershop

    Who is good with beards? I have a 3 month old and plan to let it grow. Need a little cleanup and style advice.

    I would suggest Aaron, Milos or Ricky. They can help you out and give some advice!

    Hi! Could you recommend the best barber at your shop for a low blended fade? I just moved to the area and my old barber (a real pro) typed up notes because my straight blonde hair turns a little bit (grows differently) on the right side. Thanks!

    Hi! I would suggest Milosh. We book up pretty quickly...but you can book online at www.esquirebarberchicago.com

    I have black straight/wavy medium length hair that is very thick, what barber do you recommend? I plan on keeping it around the current length, just a little trim (around half an inch). The sides and back of my hair are short

    Hello- are you going to keep your hair around the current length you have or our you going to get more of a fade haircut?

    I'm half black with pretty damn curly hair, kinda kinky on the top. Which of you should I reserve for this, if anyone?

    Hi! I would suggest Milos for your hair...when you reserve online book the 1 hr time slot. He likes to have enough time for certain haircuts.

    Don’t See Your Question? Ask Away!

    Review Highlights - Esquire Barbershop

    I logged on to Yelp for the first time in about ten years to write this review, because Aaron Johnson rules, and so does Esquire.

    Mentioned in 41 reviews

    Read more highlights

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    Funk's Barbershop - We met Mr. Funk himself!!! The best

    Funk's Barbershop

    4.4(221 reviews)
    7.2 miThe Loop
    $$

    After 10yrs of not visiting a barber i opted to visit Funk's!…read moreMan was i impressed! Great shop and James did me a solid and trimmed my beard and made me feel like i had been going there for years. Will be makin it my regular shop to visit.....pricing is just right! Pay em a visit my kings!

    Funk's Barbershop, downtown Chicago…read more Back in town for New Year's. Same trip my wife and I make every year. Same city that feels like an old friend. I needed a quick cleanup on the beard. What I walked out with was something else entirely. This was a full man pampering experience. And I'm not using that word lightly. Beard trim. Clean squared lines. Tight fade. Hot towel. Straight razor shave. Another hot towel. Beard balm and oil worked in slow and intentional. Then a clean aftershave that made the whole thing feel finished. Not rushed. Not sloppy. Done right. Joshua took care of me, and the guy is a surgeon with clippers. Quiet confidence. Knows his craft. Listens. Adjusts. Checks his work. Then checks it again. He also introduced me to Lawrence, the owner. Solid guy. Proud of his shop. You can feel that standard in the place. The vibe inside is Chicago. Cool. Relaxed. Real. No ego, but you know you're somewhere legit. You're not sitting in a chain shop where they push you in and shove you out. You sit down. You get taken care of. You walk out looking like you respect yourself again. And fellas, if you stop in, don't be surprised if you see a Chicago pro athlete sitting three chairs down. This place pulls a crowd. Highly recommend Joshua. Highly recommend Funk's. If you're in town and want to look sharp instead of hacked up, go here. Treat yourself. Let them spoil you. Then go about your night with some swagger.

    Photos
    Funk's Barbershop
    Funk's Barbershop
    Funk's Barbershop

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    Kenny Mac's Barbershop - Kenny Mac himself delivered this taper with razor lining

    Kenny Mac's Barbershop

    4.5(254 reviews)
    1.2 miUptown
    $$
    Certified professionals
    11 years in business

    We were looking for an out of town barber for a special event, which can be daunting if you're…read morerelying solely on reviews. Kenny Mac's had good reviews and a lot of good pictures so we decided to take a chance on them. Upon arrival, the place was super spacious and clean and the team was really welcoming. There was also convenient street parking and a nice area to sit while you waited for your haircut. Onto the haircut! We had the honor of having Kenny Mac himself cut my fiancés hair. He was super kind and easy to chat with during the haircut. We gave him an inspiration picture and he followed that perfectly, like it was incredibly spot on. He was super thoughtful too, asking questions and going back and forth to make sure he knew exactly what we wanted. And the outcome was impressive. I think he will do exactly what you ask him to, so if you're not happy that could be on the customer lol. He recreated the picture we sent him perfectly. The fade was fresh and sharp, and the vibes were good. It was also a good sign that there was a decent customer flow. I was also waiting around and noticed that a lot of other customers had really nice haircuts too so you can tell they really take their time to produce high quality haircuts for everyone, no matter which team member it is. We feel a lot better knowing that we have someone in the city that can do a good job and we are glad that we took a chance on the right person. He also offers mobile services throughout the city so that is really helpful. I really wish we took a fresh picture of the haircut, because now it is grown out, but I think the other pictures you see online reflect the service you receive. Also the prices were really reasonable. I'd definitely try this place out if you're looking for a high quality barber!

    Stopped in based off reviews and the scheduled barber had a emergency and wasn't there. However Zay…read morethe Manager took care of me and delivered a A1 cut and beard trim

    Photos
    Kenny Mac's Barbershop - Kenny Mac does it again... hit after hit!

    Kenny Mac does it again... hit after hit!

    Kenny Mac's Barbershop - Mohawk haircut done by Kenny at Kenny Mac's Barbershop!

    Mohawk haircut done by Kenny at Kenny Mac's Barbershop!

    Kenny Mac's Barbershop - Platinum Selling Music Artist Post Malone gets his haircut by Kenny Mac...

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    Platinum Selling Music Artist Post Malone gets his haircut by Kenny Mac...

    Van Buren Gentlemen's Salon - Bros

    Van Buren Gentlemen's Salon

    4.5(199 reviews)
    7.1 miThe Loop
    $$

    I've been going to Klaudija for a shave every week for about 6 months now. It has become the…read morehighlight of my week. She does a great job, has helped me fill out my beard to look better than ever and i get compliments on my haircuts all the time.

    Unfortunately I can not recommend this business. I committed to a quarterly member at $350, so…read more$1400 a year plus tips for a weekly beard trimmer and hair cut. The stylist was fantastic. However the customer service was sorely lacking. A membership is a different model and certainly a person's hair grows at differing rates. So when my stylist said let's not cut your hair today that was fine. A few weeks later I recieved a text message stating my appointment for that day was changed. This has happened before so I presumed something happened. Typically they reach out but I can't imagine a system errant sending a text for no reason. After I was called for being late to the original appointment time I was confused and spoke with Cassie from the front desk. She was dismissive and disrespectful when I merely tried explaining facts. When confronted her response was she was only being disrespectful because she felt I was being disrespectful to her. A wild thing to say considering the money I was committed to spending and I neither raised my voice, swore etc. After canceling due to her unprofessional attitude she then tried charging for services that were never rendered from the appointments mentioned above. This all could have been easily fixed by her remaining calm, allowing me to send the text, and we chalk it up to a system error. I could have rescheduled the appointment and they'd still have a client. To then even charge for an appointment missed resulting from their system error is disgusting. Thankfully I sent the proof to my band and we resolved it that way. Clearly Cassie has some maturation required for being in customer service. I've overheard her several times at the salon saying she doesn't care about things. And people should know how little they value a membership. Apparently they make less money on members per the stylist so I'm not sure why bother? Anyway go somewhere else where you'll be valued and respected as a client.​​

    Photos
    Van Buren Gentlemen's Salon
    Van Buren Gentlemen's Salon
    Van Buren Gentlemen's Salon

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    Esquire Barbershop - barbers - Updated May 2026

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