Careers with the City of Chicago Department of Law

If you’re looking to get hands on experience, get treated like a full-fledged attorney during your internship, or practice in just about any area of law, including both litigation and transactional practice areas, you should seriously consider the City of Chicago Department of Law for an internship, school-year externship, or postgraduate entry-level attorney position.

The City of Chicago’s Department of Law has over 270 lawyers spread out over 14 divisions so the opportunities are quite varied.

Recently, I attended a panel presentation put on by City of Chicago Department of Law attorneys who joined us to talk about their personal backgrounds and career paths, work that their divisions do, whether they hire interns, what interns do, and postgraduate hiring within their divisions.  The panel included most of the Deputy Attorneys heading each of the 14 divisions within the Law Department and the Corporate Counsel and Supervisor of the entire Department, Edward Siskel.

What do City of Chicago, Department of Law attorneys do? They are the lawyers for the city of Chicago. They advise the mayor, represent city employees,  and provide counsel to alderman. They work with General Counsel at various city departments and agencies. The City of Chicago has a very diverse practice and attorneys there have the opportunity to make a difference in challenges facing Chicago.

Department of Law attorneys engage in police reform efforts. The Labor Division negotiates with police unions. They have policy discussions on changes to police use of force policy. They help craft changes to city ordinances and guide them through the legislative process.

Edward Siskel is the Department of Law’s Corporation Counsel. As Corporation Counsel, he is Mayor Rahm Emanuel’s senior legal advisor and supervises the City’s 450-person Law Department. Mr. Siskel took time to speak with us about his incredibly varied career path and how he became Corporation Counsel for the Department. Siskel went to the University of Chicago of Law School, clerked for a judge on the 9th Circuit, clerked for Justice Stevens on the Supreme Court and then went to work for a firm in D.C, as a U.S. Attorney in Chicago,  for the White House Counsel’s office, for Wilmer Hale, and then he accepted the position as Corporation Counsel for Chicago in February 2017. He heads the entire Law Department and its 14 divisions.

Department of Law Divisions

There are ten litigation divisions, two prosecution divisions, and four transactional divisions within the Department of Law, which means that no matter what experience you are looking to get, you can get it at the Department.

Litigation Divisions:


Aviation, Environmental, Regulatory & Contracts

Collections, Ownership & Administrative Litigation

Constitutional & Commercial Litigation

Employment Litigation

Federal Civil Rights Litigation


Legal Information, Investigations & Prosecutions

Revenue Litigation


Prosecution Divisions:

Building & License Enforcement

Legal Information & Prosecutions

Transactional Divisions:

Aviation, Environmental, Regulatory & Contracts

Finance & Economic Development

Legal Counsel

Real Estate

Department attorneys get to work on very interesting projects. When I attended the panel presentation, Department attorneys were in the middle of a public debate about executive orders regarding immigration in America, so attorneys were filing amicus briefs in challenges to the travel ban and sanctuary city litigation.

Department attorneys develop as lawyers, get first chair experience, try cases, and handle cutting edge appellate and constitutional law.

On average, the Department takes 40 summer interns and 5 post graduate clerks.

Below, I will go division by division and share what each Attorney told us about their division.

Alpita Shah, Division of Aviation, Environment, Regulatory & Contracts (AERC)

Alpita went to University of Illinois for undergrad, Yale for Law school, and kept coming back to Chicago for summers. She clerked for a district court judge in the Northern District of Illinois and then worked for Mayer Brown because it was the only firm that did international transactional work in Chicago at the time. She worked in international affairs at the U.S. Treasury Department in D.C.  and then at the World Bank, where she negotiated agreements between countries and advised U.S. officials as a policy advisor and lawyer. She wanted to continue her career in public service when she returned home to Chicago so she joined the Department and has been there for 3 years.

The Aviation section of the division has local, federal and international elements. They handle regulatory issues with the FAA,and the airport  operates like a mini-city in some ways . They deal with noise issues with residents, First Amendment protests, and bond deals to finance airport capital projects. A high profile case they worked on recently with their colleagues in Torts involved a passenger being dragged off an overbooked United flight.

Alpita is at the airport 1-3 times a week.

Attorneys in this division also work on utilities issues, administrative hearings, and get other litigation and transactional experience.

Recently, an extern got to work on a research issue with the mayor’s office.

Their division has a yoga room,  and they describe themselves as the fitness oriented division within the Department. They take postgraduate fellows and recently hired a fellow as a full-time attorney.

FCRL Division:

Susan Song, Collections, Ownership & Administrative Litigation Unit:

Susan went to Chicago-Kent for law school, clerked on an Illinois Appellate court, and then joined the Department of Law. She has worked in several divisions.

There are 49 people working in her unit. Collections collects over 150 million in fines. Ownership does all title analysis such as determining who the owner of a building is when that building receives a building code violation.

Interns working in Collections, Ownership & Administrative Litigation will get hands on experience. The division takes 10-15 law clerks and not all need a 7/11 license. Most of the work in the divisions is in ownership or collections.

Interns in this division get assigned to a mentor who reviews their work.


The Collections Section handles in-house collection and cost recovery matters, advises City departments on collection and revenue issues, and supervises outside collection law firms who handle collections, cost recovery and benefits subrogation matters for the City.  Through its in-house and outside collection efforts, the Section collects more than $150M annually.
In-house attorneys also handle a wide variety of tasks focused on collecting money owed to the City and preventing or defending collection-related claims against the City.  These matters are litigated in state and federal court as well as the City’s Department of Administrative Hearings.


The Ownership Section is responsible for conducting title research to determine real property ownership and proper service addresses for responsible parties who have property related violations of the Municipal Code of Chicago.  Ownership information is provided to the client departments to use in preparation of litigation at the Department of Administrative Hearings or in circuit court.  Attorneys in this Section conduct hearings at the Department of Administrative Hearings for ownership dispute matters.  The Section conducts approximately 45,000 title searches annually.  The Section also works closely with client departments to ensure quality and accuracy of citations and complaints issued by City departments.

Liens and Acquisitions

The Liens and Acquisitions Section oversees the City’s inventory of priority demolition liens and other property liens created by the Illinois Unsafe Property Act.
Additionally, attorneys in this Section defend the Department of Planning and Development (DPD) in mortgage foreclosure proceedings involving DPD loans and regulatory agreements; handle all mechanics lien claims and surety bond claims against the City that involve City-owned property; manage all property-tax take notices; and litigate property-tax contested issues in matters involving priority liens.


The Bankruptcy Section is responsible for protecting the City’s interests when debtors file bankruptcy cases under Chapter 7, 11 and 13 of the United States Bankruptcy Code.   Attorneys in this Section handle in-house bankruptcy cases and supervise outside law firms who represent the City in bankruptcy matters.   Attorneys also provide legal advice and counseling on a wide range of bankruptcy issues to other divisions within the law department and various City departments.

Federal Civil Rights Litigation

The FCRL division has 44 attorneys.

The Federal Civil Rights Litigation division defends the cops. Attorneys handle common-law police misconduct cases, such as excessive force, false arrest, malicious prosecution, extended detention, and reversed conviction that are filed in the First Municipal Department of the Cook County Circuit Court.

The division attorneys stated that when one person goes to trial, we all go to trial. They have regular team meetings to talk about cases and are at the cutting edge of civil and police litigation.

Attorneys from the division said they recently had a case in federal court where the state alleged that the police strangled someone to death, but it turned out that the individual had done heroin. In that case, the extern argued motions, helped prepare witnesses for trial, and got to participate in mock closing arguments and cross examinations. If you have a 711 license, you can take depositions and try cases as a 3rd chair in federal court. 30-48% of all cases tried in federal court in the Northern District of Illinois involve the Federal Civil Rights Litigation division. If you want to argue before judges, this division is the place for you. No one does anything on their own. They are a very collaborative team.

They recently hired 13 former externs and volunteers so if you want to get hired into this section as an attorney, externing there is huge.

Eileen Geary, Labor

The Labor Division handles traditional labor and employment discrimination at the agency level and handles all issues regarding discipline of employees. The city has 35,000 employees, most of whom are in a union and the Labor Division handles all of the issues that arise from these 35,000 employees.

The Labor Division drafts charges against employees, present those charges to departments, and advises them throughout the disciplinary process. They deal with very serious issues and are involved mostly when employees are really getting punished.

The Labor Division interacts a lot with the City of Chicago Human Resources Board and Police Board. They also handle separation or discharge cases with police officers.

The Labor Division participates in many full evidentiary hearings and handles charges filed at the EEOC. They investigate allegations, interview witnesses,  and draft responses to the charges.

Additionally, cases the Labor Division handles can be heard at the Illinois human rights commission.

The Labor Division also counsels city departments in different areas like ADA, FMLA, leaves of absence, violence in the workplace, Military leave act issues, and Illinois domestic violence statute issues.

Lastly, the division handles traditional labor issues. They have labor negotiators who work on negotiating contracts for collective bargaining agreements, they handle arbitration hearings, go before the Illinois Department of Labor and Labor Board, and draft settlement agreements.

If you intern with the Labor Division, you will get some good writing samples.

Mark Harrison, Torts

Mark Harrison worked for the City of Chicago during his second year summer and joined the division right after law school graduation. He switched to the torts division in 1995 from the building division.

The Torts Division tries a lot of cases to juries and has about 25-30 trials each year. People tend to stay in the division because it is collaborative and the division has strong teamwork.

In Chicago, most torts claims against the city mostly involve people getting injured driving vehicles. They see everything from sprains to paralysis and loss of limb.

Younger attorneys immediately get involved in litigation writing motions, going to court, and representing the City at arbitration hearings.

The Torts Division tries a lot of cases to juries and has about 4-8 trials each year. People don’t really leave the division because it is collaborative and the division has strong teamwork. Mark describes the Torts Division as resembling summer camp. The attorneys frequently eat lunch together.

If you’re looking to work on trials, the Torts Division is a great place for you.

Kim Roberts, Building & License Enforcement Division

Kim started working at the Department during law school as a 711 clerk and has worked there for 17 years. The Building & License Enforcement Division consists of 8 different sections. 6 sections deal exclusively with enforcement of the Chicago building code, one revokes licenses, and one investigates potential building code violations.

The division prosecutes issues such as landlords failing to provide heat to tenants, hoarding complaints, developers skirting laws and the building codes, zoning issues, and issues with drug and gang house enforcement. This division works closely with the Chicago Police Department; they refer problem properties to them and file cases in housing court. They use court orders to eliminate problems.

You should intern for this division if you love hands-on experience. While working as an intern here, you will go out with inspectors to visit properties and go with the police in bullet proof vests. You will see what is going on in Chicago neighborhoods, go to court, and see building enforcement issues play out from beginning to end. It’s quick and not bogged down with complex litigation. Their division is shaping communities.

Jim McDonald, Finance & Economic Development

Jim worked at Chapman & Cutler in Chicago doing public finance transactions for several years,  went traveling for 2 years,  and then came to the Finance Division. He has been working in that division since 1990.

As one of the Department’s four transactional divisions, the Finance Division does not go to court. The division has 13 lawyers and most of them have been there a long time. It is transactional work. The City gets money from the federal government, state government, and private grantors, and those transactions need to be documented.

They also work on economic development projects such affordable housing. The City’s Planning and Development Division is their client, and they work a lot with the Chicago Housing Authority. One of their big recent projects was the Chicago Riverwalk; Finance Division lawyers did the financing for it. They got $98 million as a loan from the Department of Transportation. They also recently worked on a parking garage built with bonds issued by the city.

The Division also worked on the City of Chicago’s parking meter concession where the city got $1.5 billion for a 75 year concession. Jim said you can walk around the City of Chicago and see the results of the Finance Division’s work.

The division is looking for people who are flexible and can get started right away. There is no need for a 711 license. The division has a lot of work and will give interns and externs as much as they can handle. Interns will get research questions, they will get to draft ordinances authorizing transactions, sit in on negotiating sessions with development, go to finance meetings with alderman, and go to real estate closings.

The division regularly hires externs and hires former externs as attorneys. A former summer clerk is now senior counsel in the Finance Division.

Jeff Levine, Deputy of Legal Counsel Division

Jeff went to Georgetown for law school, completed an  8th Circuit clerkship after graduating, and then worked at Mayer Brown. He has been with the Legal Counsel Division for 22 years. He specializes in legislative drafting and advisory work.

The Legal Counsel Division works on issues that are at the intersection of law and policy. Recently, they have engaged with issues such as protesters wanting to put balloons over Trump Tower and assessing what permits they need and drafting ordinances regulating ridesharing, Airbnb, and drones.

The Legal Counsel Division takes on as many interns as they can and turns them into a full-fledged division attorney to the full extent that they can rather than putting them in a hierarchical situation.

The Constitutional and Commercial Litigation,  Real Estate, Employment Litigation, Revenue, Legal Information and Prosecutions, and Appeals divisions were not able to attend but all of those divisions provide great experience and you can read more about them on the City of Chicago website. You can read more about all of the divisions in the City’s viewbook.

Externing with the City of Chicago

Students can work with the City of Chicago during the summer. Positions are unpaid but they qualify for Notre Dame’s federal work study funding.

Divisions will take students who can work 10-15 hours a week but it is a better experience if you can work full time. If you have a 711 license, you can appear in court. Notre Dame students can work for the City of Chicago Department of Law full-time during the fall or spring semester through the Notre Dame Law in Chicago program or a couple of days per week during the semester through Notre Dame’s Lawyering Practice externship.

Division hiring is limited by the number of supervisors and the size of the department. For instance, the Legal Counsel Division has a small group so they cannot take on a lot of externs. By contrast, the Building and License Enforcement Division can take 12 externs. The Collections, Ownership, and Administrative Litigation Division can take a lot of externs as well. The Federal Civil Rights Litigation Division takes 8 externs over the summer. The Division of Aviation, Environment, and Regulatory took 3 externs last summer and recently hosted a 2017 NDLS graduate as a Bridge-to-Practice fellow.

The Department is not extremely competitive but  the later you apply, the fewer choices you will have. When you apply, you list your top three divisions. If a particular division is full, the Recruiting Manager will keep shopping your application around until there is a division that can take you. 

If you are interested in externing, then don’t wait. They hire on a rolling basis. If you don’t follow the rules for applying, you will not be considered.

The Department accepts applications for summer positions between January 15 – March 1.

You can find the instructions for applying here. Please note that applications must be mailed in and email applications are not accepted so be sure to apply early. 

Postgraduate, entry-level attorney hiring

Notre Dame 3Ls who wish to work at the Department after graduation can work there through Notre Dame’s Bridge-to-Practice Program. There are NDLS graduates working there as Bridge-to-Practice fellows now. There is no guarantee that you will get hired when your fellowship concludes but it does happen.

If you work with one division after graduation, you can still get hired by another division later.

If you are interested in an entry-level job with the Department, they recommend creating a profile on their website and getting emails set up from their job search agent so you know as soon as positions are posted.

Salaries are based on legal experience and there is no fixed starting salary but in the past, we have known ND grads who earned $60-65K as attorneys starting at the Department.

Insider application tips from Division leaders (do grades matter?)

I asked how much weight different divisions assign to grades. Some supervisors care about grades and some do not. The head of Federal Civil Rights Litigation Division, stated unequivocally that she doesn’t care about grades. Alpita Shah, the head of the Aviation Division, does care.

Many supervisors cared most about a good attitude and the ability to hold a conversation rather than grades.

The Federal Civil Rights Litigation division elaborated on what they look for in externs, stating that they “wants ballers.” They are very protective of the atmosphere in their division, which is very collegial and team oriented. It is very bad if a candidate only talks about what they want and asks questions about how many hours they are expected to work and what the division does. You should know what the division does when you interview and be ready to work hard. The division wants people who are passionate about defending the cops, going out on the scene, and are interested in the work. In this division, you get experience and depositions very fast so you need to be ready for that.

The division also encourages applicants to pay close attention to detail when applying. They once had an applicant address an application to them but say that they wanted to work for the state’s attorney.  Basically, he was saying he couldn’t get job with the state’s attorney but the Federal Civil Rights Litigation Division was close enough. He didn’t get an interview.

Kim Roberts, who heads the Building and License Enforcement Division, doesn’t care about grades but wants to see a cover letter that is specifically tailored to her division. You need to care. Her attitude is that her division can groom a student into a good attorney but they have to be motivated. She looks for that motivation.

Ed Siskel, the head of the Law Department, does look at grades but he recognizes that not everyone knows how to take law school exams. For him, it is important that you take relevant classes and have a demonstrated commitment to public service. Take classes related to the division you are interested in. For example, take trial advocacy if you want to work for the Torts Division.

Jeff Levine, who heads the Legal Counsel Division, wants a cover letter tailored specifically to a position in his office. He says that some see a fully developed cover letter as outdated but he looks very carefully at the cover letter. If he sees typos or misspellings, that’s death. In his view, if you can’t take the time to make the cover letter just right, it shows an overall lack of care.

When it comes to postgraduate hiring, the deputy attorneys review applications and decide who to interview. They make recommendations to Ed. Ed reviews files and either agrees or disagrees with the recommendation.

You can get great experience externing with the City of Chicago Department of Law. If you’re interested, meet with me and I can help you prepare your application materials.

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