The 7 Best Small Business Insurance in Chicago

Thang Truong
Thang Truong
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Home to more than 2.7 million residents, Chicago is the most populous city in the state of Illinois and the third largest in the United States. 

Chicago started out as a small trading post on the mouth of the Chicago River. It grew exponentially over time to become one of the greatest cities in the U.S. and a top location for small businesses. The city is a leader in finance, insurance, commerce, industry, technology, telecommunications, and transportation in its state, the midwest, and the country, as well.

Chicago is a hotbed of small business creativity. The one thing all these creative Chicago small businesses share in common is that they face many, many risks. These include things like fires, customer and employee injuries, theft, lawsuits, and more. The most important thing business owners can do to get control over these risks is to get business insurance coverage, which can protect you against all these things and much more. 

In this article, we’ll cover the top seven business insurers in Chicago. We’ll also provide information about business insurance in general and different types of coverages so you have the knowledge you need to get the right protection at the best possible price. 

Top 7 small business insurance companies in Chicago

Here are our choices for the best business insurers in Chicago and what makes each unique.

  • CoverWallet: Best for comparing online quotes
  • biBerk: Best for low-cost business coverage in Chicago
  • THREE: A one stop shop for all your Chicago business insurance needs
  • Next: Ideal for business owners who prefer to buy insurance online 
  • Hiscox: Best for Chicago small businesses with unique insurance needs
  • The Hartford: Best for businesses looking for a solid and ethical insurer
  • Progressive: Top insurer for discounted Chicago business insurance

CoverWallet: Best for comparing several online quotes

As any small business is tight on budget, comparing several online quotes to find the cheapest one is important. If that describes your situation, you may want to start with CoverWallet.

CoverWallet is a digital broker specializing in small businesses. They provide a wide range of insurance coverages for small businesses of almost all industries. So, regardless the industry your small business is in, you can rest assured that CoverWallet will be able to find quotes for you.

Their online quote form is simple and intuitive, it shouldn’t take you more than 10 minutes to complete it and start comparing quotes to choose the best one for your business.

biBerk: Best for low-cost business coverage in Chicago

After the last few years of economic uncertainty, few businesses are sitting on extra cash to spend on insurance. If that’s the case with your Chicago based business, biBerk could be the ideal insurer for you. 

biBerk is a low-cost business insurance provider. Despite saving money on your business coverage, you can rest assured knowing you’re still getting quality protection for the operation you’ve worked so hard to build. biBERK is able to lower insurance costs by almost 20 percent because it insures small businesses directly, without the added expense of having to work through a middleman or insurance broker.

You can feel confident knowing biBerk is a part of Berkshire Hathaway, a company headed by well-known investor Warren Buffett. It’s a firm that has millions of satisfied customers that’s been insuring businesses for more than 75 years.

THREE: A one stop shop for all your Chicago business insurance needs

If you’re a busy Chicago business owner who doesn’t have much time to shop for insurance, THREE could be the ideal solution for you.

THREE is also a part of the Berkshire Hathaway family of companies. It offers a single policy that covers most of the risks faced by all types of businesses. The firm prides itself on the fact that it has a simple three page policy with no fine print or surprises. 

The single policy covers:

  • Liability: General liability, errors and omissions, and employment practices
  • Cyber: Cyber liability, data compromise, and incident response
  • Property and business interruption: Fire, theft, flood and water damage, wind and hail
  • Business auto: Collision, comprehensive, auto liability, and hired and non-owned
  • Workers compensation.

If simplicity and comprehensive coverage are important to you, THREE could be a good provider for your business insurance.

Next: Ideal for contractors who prefer to buy insurance online 

Next is changing how businesses purchase insurance. Their first focus industry is contractors. If you are a contractor in Chicago, you will definitely need to get a quote from NEXT.

The operation is focused on delivering the ultimate online insurance experience. Because of this, you’re able to purchase a policy, file a claim, or get a certificate of insurance any place, any time, 365 days a year. Even though Next is an online insurer, you can get expert help over the phone when you need it. The firm is also known for being able to make most claims decisions within 48 hours.

Even though Next is a relatively new and innovative company, you can rest assured knowing it has an excellent rating from A.M. Best, an insurance company rating agency. All the company’s policies are backed by MunichRe, an established insurance company and reinsurer. More than 10,000 business owners have turned to Next for their insurance needs, including many in the Chicago area. The firm has earned a solid 4.7 customer rating. 

Hiscox: Best for Chicago small businesses with unique insurance needs

Hiscox offers a complete array of business coverages and is a leading insurer that specializes in small business insurance. 

Hiscox makes it easy to purchase all types of business insurance online. You can also speak with experienced business insurance experts who can help you customize your coverage to meet your unique company needs. Hiscox also offers top tier service, provides fast quotes, instant coverage, and quick claims processing.

If you choose Hiscox for your business coverage, you can rest assured knowing you’re entrusting your organization to a firm that’s been in operation since 1901. More than 400,000 companies choose Hiscox for their coverage.

The Hartford: Best for businesses looking for a solid and ethical insurer

The Hartford is one of the oldest companies of any kind in the United States. It’s offered insurance solutions for more than 200 years and has helped one million plus businesses with their insurance needs, including many in Chicago. The company takes pride in the fact that the Ethisphere Institute named it a World’s Most Ethical Company twelve times. The Hartford’s longevity and focus on ethical business practices makes it a company that you can feel good about doing business with.

The Hartford’s dedicated and highly experienced small business team is available to help company owners explore their insurance options. If you decide to purchase insurance from The Hartford, you can rest assured knowing you’re entrusting your business to a strong, stable, knowledgeable, and ethical provider.

Progressive: Top insurer for discounted Chicago business insurance

Despite the image it projects in its television commercials, Progressive is a serious and reputable company that’s been in business since 1937. The insurer is known for its flexibility, great rates, and highly responsive service.

Progressive is famous for its discounts, which could help you save on your business insurance. You can earn them for things like:

  • Purchasing multiple coverages
  • Implementing safe work practices 
  • Paying annually rather than in smaller increments 
  • Agreeing to autopay.

It’s easy to get a quote online from Progressive. It should take you less than five minutes.  

What is business insurance?

Business insurance, also known as commercial insurance, helps protect business owners from unexpected losses.

There are many types of business insurance options to help cover your Chicago based operation for property damage, legal liability, and employee-related risks. 

What is business insurance for?

Business insurance can help you gain control over your company’s risks, which are considerable. It provides you with financial protection against losses that occur while conducting business. When you have business insurance coverage, your insurer helps pay the costs of covered losses up to the limits of your policy. Without coverage, you might have to pay out of pocket, which can easily bankrupt your business. 

Why do I need business insurance in Chicago?

First and foremost, some insurance coverages are required by laws. Workers comp insurance and commercial auto insurance are required for all small businesses in Chicago.

The purpose of the insurance is to help protect your Chicago company from common risks most businesses face, along with industry specific ones. It can protect the financial assets of your company, it’s physical property, employees, and intellectual property from:

  • Lawsuits
  • Property damage
  • Theft
  • Vandalism
  • Loss of income
  • Employee injuries and illnesses
  • And more.

What kinds of business insurance do I need in Chicago?

The most common types of business insurance coverage small companies in Chicago typically purchase include:

What is workers’ compensation coverage and do small businesses need it in Chicago?

If your business has employees, the state of Illinois, with few exceptions, will require you to carry workers’ compensation coverage.  This insurance provides benefits to your employees to help them recover from work related injuries or illnesses. Some examples of these include:

  • A clerk at your store is stocking shelves, slips off a ladder, and breaks her leg. This makes her unable to do her job.
  • An administrative assistant at your business has been working on a computer while sitting on a cheap old chair and comes down with carpal tunnel syndrome. She is no longer able to do her job because she’s in pain.
  • A carpenter at your cabinet factory has been breathing in saw dust and chemical odors for years and comes down with lung disease. His doctor will not allow him to return to work.

Workers’ comp also pays funeral expenses and death benefits to immediate family members should an employee pass away because of a job related incident. 

Learn more about workers comp insurance and the best workers comp insurance companies and the cheapest workers comp insurance companies.

Commercial auto insurance in Chicago 

Commercial auto insurance pays for damage to vehicles and property and the cost of medical care if you or an employee is involved in an accident while driving for work related reasons. It is required in Illinois to have commercial auto insurance for your business. Personal auto insurance doesn’t cover you and your vehicle if you drive for work reasons.

If you don’t have proper business vehicle insurance and are involved in an accident when you are driving for work, your personal auto insurance company will refuse the claim and might drop you from their coverage as well. Learn more about the differences between commercial auto insurance and personal auto insurance and why small businesses need to have commercial auto insurance coverage. 

Commercial auto insurance is usually a bit more expensive than personal auto coverage, but without it, you may have to pay out of pocket a lot more. Learn more about the coverage and how to find cheap commercial auto insurance.

General liability insurance in Chicago

General liability insurance, also referred to as commercial liability, helps protect your business against claims of non-employee bodily injury and property damage that happen in your workplace or while your employees are doing their jobs. This includes things like customer injuries that result from a slip and fall in your office or workplace or client property damage that occurs because of a worker incident in a client’s home or business location. 

General liability insurance isn’t required by state law in Illinois for most small businesses. However, it is probably the most popular coverage for them to carry. Learn more about this coverage and the cheapest general liability insurance companies

What does a Business Owners Policy (BOP) cover in Chicago? 

A Business Owners Policy (BOP) will help protect your business property, income, and financial assets. A BOP typically includes three types of coverage:

Business property insurance protects the buildings your business operates out of, whether you own or rent them and the equipment used to run your company. This includes your:

  • Physical location
  • Tools
  • Inventory
  • Supplies
  • Computers
  • And more.

General liability insurance covers legal claims against your business related to:

  • Bodily injury
  • Property damage
  • Reputational harm, such as libel and slander.

Business income insurance, often referred to as business interruption coverage, helps replace lost income if you can’t operate your business because of property damage that’s covered by your business policy. This includes damage from fire, wind, weather events, and burglaries. Learn more about the best business income insurance companies.

Depending on the specific needs of your business, you can work with your insurance agent or company rep to figure out what other coverages you may need.  

Professional liability insurance in Chicago 

Professional liability insurance covers you and the people who work for you if you’re ever sued by a client for giving them bad advice or not performing services to their satisfaction.

If you are in a business that provides clients with advice or customers with recommendations, you might need professional liability insurance. It’s also called errors and omissions (E&O) coverage in real estate, insurance, or finance, and malpractice insurance in the healthcare and legal professions. 

Coverage details differ by industry and specialty. Use our guides to help you find the coverage that’s right for you: 

Other insurance coverages small businesses in Chicago might need

Check out other protection businesses in your area typically get.

Learn more about the 15 types of business insurance and who needs to have them.

How can I prevent business losses in Chicago? 

Many business insurers offer programs that can help you reduce business related risks. This includes doing things like eliminating workplace hazards and encouraging safe work practices. By doing these things, you could be able to save on your business insurance costs. Check with your business insurer to find out whether they offer workplace safety programs.

Is there an easy way to get business insurance coverage in Chicago?

The simplest way to get small business insurance coverage is through a business owners policy (BOP), which typically bundles together business property and liability coverage. A BOP makes it easy to add on additional types of coverage beyond these.

The types and amount of coverage you need depend on a number of factors including: 

  • Your industry 
  • The size of your business
  • It’s location or locations
  • The number of employees
  • And more.

At a minimum, you probably want to have liability and property coverage through a BOP. And if you have employees, the state of Illinois will likely require you to get workers’ compensation insurance. When you apply for coverage online, it’s likely that the insurer will suggest the additional coverages you should get. An experienced business insurance agent or company rep will be able to recommend coverages to you, as well.

How much does small business insurance cost in Chicago?

The average cost that small businesses in Chicago pay for their insurance coverage is $1,450 a year.

Premium costs can vary dramatically because they’re based on so many factors including:

  • The age and value of your business property
  • The contents of your property
  • Your business type
  • Where in Chicago it’s located 
  • The limits and coverage options you choose
  • Whether or not you select full or partial replacement cost
  • And more.

What’s important is that you get quotes from multiple providers so you can compare coverages and costs to get the best and most cost effective coverage for your business.

How can I find cheap business insurance in Chicago?

Here are some tips to help you find the coverage you need at a fair price:

  • Shop around. Get quotes from a few companies or compare them to get the coverage you need at the best possible cost. 
  • Don’t stop shopping around. Make sure you get new quotes before you renew your policy.
  • Take advantage of discounts. If they’re not offered to you when getting a quote, ask about them, whether you’re buying online or through an agent.

Taking these steps will help ensure you’re not paying too much for your small business insurance.

Highlight some small business creativity in Chicago

Chicago is a hotbed of small business creativity. Business Insider recently put a spotlight on some of the most unique and interesting small companies in the city.

  • ACME Hotel Company is a high-tech alternative boutique hotel that caters to a very hip clientele. Not only does it offer tech-savvy hookups like lightning fast Wi-Fi and big screen LED TVs in every room, the rooms are also decked out in a subtle alt-rock theme. The hotel has its own Spotify playlist.
  • bethie b is a company that specializes in hand-painted and custom made pillows. The founders are a mother and daughter pillow creating team with an eye for the unique, creative, and handmade. They also sell recycled decorative items.
  • Belmont Barbershop is an operation straight out of the history books. It’s known for creating classic men’s looks. Customers can browse comic books while waiting for their cuts.
  • The Boring Store sells everything you need to become a secret agent. Along with fake mustaches and high-tech surveillance equipment, the Boring Store is actually a front for a non-profit writing and tutoring center for local students.
  • CONE is an Irish ice cream parlor, creating flavors like Bailey’s, Guinness, Irish Mint Chip, and Jameson.
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Thang Truong
Thang Truong

Thang Truong covers small business insurance and small business success at BravoPolicy. He is a licensed P&C insurance agent. Previously, he held product leadership positions at, Capital One, NerdWallet, and Mulberry Technology. He holds a MBA degree from UC Berkeley - Haas School of Business.

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