Finding contract work isn’t always easy. It requires knowledge of what available opportunities exist and an understanding of the nuances of local regulations. If you’re looking to get started on contract work in Chicago, you’ll need to consider a variety of factors—from what qualifications and credentials you need to the different legal requirements, contracts, and taxes associated with working as a contractor in the Second City.

When it comes to freelancing, Chicago has some of the most comprehensive business laws in the United States. This means that understanding the local regulations can help you to be a successful contractor in the city. Understanding the differences between an employee and an independent contractor is a key concern when it comes to contracting work. The IRS has a series of factors that it uses to differentiate between the two, including “Behavioral Control” (What types of instructions are given?), “Financial Control” (Who controls the finances?), and “Relationship Type” (Are there written agreements?).

When it comes to irregularities, one of the most important considerations is the number of days or hours you work within a calendar year. In Chicago, contractors must have a total of 20 days (or 40 hours) of work within a calendar year to be considered an independent contractor. The city also requires that contracts provide 90 days of notice before they are terminated.

Meanwhile, the city requires that all contractors and freelancers working there register with the Business Affairs and Consumer Protection Dept., where they must pay a registration fee as well as filing a business activity report. Additionally, freelancers must obtain a city sticker or a Chicago business tax return stamp to complete their registration. As part of the process, contractors must also obtain a $7,000 “IPRA” (Illinois Public Resources Act) bond – which serves as a security that the contractor will properly deliver the contracted product or service.

Once you are certain you fulfill all of the requirements, the next step is to find contract work. For this, you’ll want to build a reputation both online and offline. Of course, that means having and utilizing a strong online presence. Buildingsocial proof through user reviews, ratings, and endorsements is immensely helpful, and is often the deciding factor between you and your competitors. Offline, networking is your best bet. Attend local industry events and seminars, and build relationships with those in the field who can help you find contracts.

For help with legal support you may also consider working with an experienced business lawyer. With expertise in understanding business law, contract law, and local regulations, business lawyers are best suited to help contractors effectively fulfill legal requirements when it comes to hiring practices and document review. Whether you need a one-time consult or a legal department to handle short and long term contracts, UpCounsel, a leading online attorney network, can help.

At UpCounsel, you can access experienced and highly rated attorneys with over 14 years of experience. With ratings, reviews, and transcripts of experienced lawyers, you can be sure that you are connecting with the best legal advocate for your particular needs. With a large network of attorneys and a business-first approach, you can rest assured that your contracts and agreements will be legally sound and compliant with the Chicago regulations.

At the end of the day, understanding the regulations in your particular area and leveraging the right resources at the right time to get the best outcomes is key. Get out there, network, utilize online resources, and build your online network and reputation. With clear expectations and the right support from experienced business attorneys, contract work in the Second City is within your grasp.


Contract Work,

Local Regulations,

Chicago Business Laws