Getting a tattoo is easy. Getting the right tattoo artist for your specific idea is where things get complicated — especially in a city like Chicago where there are hundreds of tattoo shops and thousands of artists to choose from.

If you are looking for a custom tattoo, this is not something you should rush into or base solely on price. The artist you choose will determine not only how your tattoo looks, but how the entire experience feels from start to finish.

After years in the tattoo industry and working with clients from all over Chicago and beyond, we have seen firsthand what leads to amazing tattoos — and what leads to regret, coverups, and bad experiences.

Here is what you should actually look for when choosing the right custom tattoo artist in Chicago.

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1. Choose an Artist Based on Their Style — Not Convenience

One of the biggest mistakes people make is walking into a random shop and letting whichever artist is available do the tattoo.

Not every tattoo artist specializes in the same type of work. Someone who excels at traditional tattoos may not be the best fit for fine line, realism, Japanese, anime, or black and grey work.

The first thing you should ask yourself is:

“Does this artist already create tattoos that look like what I want?”

If the answer is no, keep looking.

A great custom tattoo starts with choosing an artist whose natural style already matches your vision. You should never expect an artist to suddenly tattoo in a completely different style than what they consistently show in their portfolio.

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2. Research the Artist Beyond Instagram

A polished Instagram page is not enough anymore.

When researching tattoo artists in Chicago, look at their work in multiple places:

• Their shop website
• Their Instagram portfolio
• Healed tattoo photos
• Client reviews
• Tagged photos from real clients

You also want to pay attention to consistency. Does the quality look solid across years of work, or only in a few recent posts?

Experience matters.

An artist with years of consistent, high-level work is usually a safer investment than someone newer who only posts heavily edited highlight photos online.

It is also smart to make sure the artist is actually affiliated with the shop they claim to work at. Unfortunately, tattoo scams and fake profiles have become increasingly common.

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3. Pay Attention to the Shop’s Reputation

One thing many people overlook is that all tattoo shops are not created equal.

The reputation of the shop says a lot about the type of artists they hire and the experience they provide.

Before booking, research:

• Google reviews
• Client testimonials
• Cleanliness
• Professionalism
• Shop atmosphere
• How clients describe their experience

A good tattoo shop should feel welcoming, organized, and professional from the moment you walk in.

If the shop feels dirty, chaotic, or unfriendly, that is a major red flag.

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4. The Consultation Matters More Than People Think

A consultation is not just about discussing the tattoo design. It is your opportunity to see if the artist is actually the right fit for you.

A few major green flags during a consultation include:

• The artist listens carefully
• They ask thoughtful questions
• They explain the process clearly
• They make you feel comfortable
• Their communication feels professional and respectful
• Their personality and “vibe” match what you are looking for

If you are getting a large custom tattoo, you may spend multiple sessions and many hours with this person.

You should genuinely feel comfortable around them.

A technically skilled artist with a bad attitude can still create a terrible overall experience.

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5. Do Not Choose a Tattoo Artist Based on Price Alone

This is one of the hardest lessons people learn in tattooing.

Cheap tattoos often become expensive coverups later.

While you should absolutely look for fair pricing, choosing the lowest price usually leads to disappointment. Artists who charge significantly less than the market average often:

• Have less experience
• Have smaller client demand
• Produce inconsistent work
• Lack long-term portfolio depth

A better approach is to research average tattoo pricing in Chicago and compare artists within that range.

If the artist you truly want is outside your budget, consider:

• Saving up longer
• Going smaller with the design
• Splitting the project into sessions

Remember: tattoos are permanent.

Waiting for the right artist is always worth it.

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6. Look for Healed Tattoos — Not Just Fresh Ones

Fresh tattoos almost always look brighter and sharper immediately after completion.

Healed tattoos tell the real story.

When researching artists, try to find healed examples of their work. This gives you a better understanding of:

• Line quality
• Saturation
• Longevity
• How their tattoos age over time

A strong artist should be proud to show healed results. But please remember that your skin is always changing. Every tattoo will fade and spread. A good tattooer knows how to ensure that even when the tattoo changes over the years, it will still look good.

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7. Your Experience Matters Just as Much as the Tattoo

One thing the tattoo industry overlooked for years was customer experience. When we started Speakeasy Custom Tattoo in 2008, the customer experience was our main focus and this remains the same today.

Today, clients want more than just good artwork. They want to feel comfortable, respected, and taken care of throughout the process.

A great tattoo experience includes:

• Friendly staff
• Good communication
• A welcoming atmosphere
• Cleanliness
• Professionalism
• Comfort during long sessions
• Feeling heard and respected

At Speakeasy Custom Tattoo, creating a positive experience has always been a major priority. From greeting clients at the door to making sure they are comfortable during long tattoo sessions, the goal is to create an environment where people actually enjoy the process — not just endure it.

That level of care is something many people do not realize they should be looking for until after they have had a bad experience elsewhere.

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8. First-Time Tattoo Clients Should Not Feel Intimidated

Getting your first tattoo can feel overwhelming.

There are endless styles, artists, opinions, and horror stories online. A good shop understands that and helps guide clients through the process instead of making them feel judged or pressured.

Even if you only have a rough idea — like wanting a tattoo of your dog or a meaningful memory — a strong custom artist can help shape that idea into something beautiful and lasting.

The best tattoo artists do not just tattoo well. They communicate well.

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Final Thoughts: Choose Carefully — You Wear It Forever

If there is one thing to remember when choosing a custom tattoo artist in Chicago, it is this:

Not all artists — and not all tattoo shops — are equal.

Take the time to:

• Research thoroughly
• Study portfolios carefully
• Read reviews
• Meet the artist in person
• Pay attention to how the shop makes you feel
• Choose quality over cheap pricing

The right artist will not only give you a great tattoo — they will give you an experience you feel good about for years to come.

Because in tattooing, the cheapest option often ends up costing the most in the long run.