Jessica L. Ryan

Principal

Community Association Law, Landlord & Tenant Law
Illinois

Contact

Jessica Ryan joined Kovitz Shifrin Nesbit in 2001 and became a principal of the firm in 2011. As head of the Landlord/Tenant Department, she has extensive experience in assisting landlords and property managers with rental property issues, including: evictions, building code violations, construction defect litigation, disputes (third party, tenant, vendor), and lease/contract review to confirm compliance with state statutes and local ordinances.

Jessica has a wide-range of experience in landlord/tenant litigation and is well-versed in the Chicago Residential Landlord Tenant Ordinance (RLTO) as well as the Cook County Residential Tenant and Landlord Ordinance (RTLO).

Jessica also assists condominium, homeowner (HOA), and townhome associations with forcible entry and detainer issues, covenant and rule enforcement, and collection of damages and fees. In addition, she has successfully argued before the Second District Appellate Court and prevailed over Motions brought in the Illinois Supreme Court.

Jessica is a frequent speaker at industry tradeshows and community seminars. She regularly contributes articles to local and national publications addressing relevant and timely landlord/tenant issues. She currently serves on the Chicagoland Apartment Association (CAA) Board of Directors and acts as local counsel to the National Apartment Association.

Education

J.D., University of San Diego School of Law, 1999
B.A. (English, minors in French and Psychology), Indiana University, Bloomington, 1995

Admissions

Illinois State Bar
U. S. District Court, Northern District of Illinois (Member, Trial Bar)

Memberships

Illinois State Bar Association
Chicagoland Apartment Association (CAA)
CAI Illinois – Community Associations Institute

Podcasts

- “Understanding Abandonment for Illinois Landlords and Rental Property Managers” – KSN landlord/tenant attorney Jessica Ryan discusses how Illinois landlords and rental property managers should handle tenant abandonment. This episode will cover what constitutes abandonment under Illinois law, the legal steps landlords must take before entering or re-renting a unit, handling abandoned property, avoiding liability, and how abandonment interacts with notices and other landlord responsibilities. Jessica will also touch on relevant legal updates and best practices to stay compliant with federal, state, and local regulations. (57 mins.)
- “Eviction Basics for Illinois Landlords and Rental Property Managers” – KSN landlord/tenant attorney Jessica Ryan discusses immigration enforcement and the impact to Illinois landlords and rental property managers. Topics include adhering to updated laws (federal and state plus local ordinances), landlord responsibilities, notices, liability, potential violations, rental assistance, and more. (63 mins.)
- “ICE Raids, Immigration Enforcement, & Rental Properties: What Illinois Landlords Need to Know” – KSN landlord/tenant attorney Jessica Ryan discusses immigration enforcement and the impact to Illinois landlords and rental property managers. Topics include warrants, property owner rights, interacting with Immigration and Customs Enforcement (ICE) and Department of Homeland Security (DHS) agents. (66 mins.)
- “2025 Chicago and Illinois Landlord Legal Updates” – KSN landlord/tenant attorney Jessica Ryan discusses important legal updates impacting Illinois landlords and rental property managers. Topics include Landlord Retaliation Act, tenant credit reports, flood disclosure, serving lawsuits, RLTO updates, rental assistance, and more. (60 mins.)
- “Chicago and Illinois Landlord Legal Updates: Preparing for 2025” – KSN landlord/tenant attorney Jessica Ryan discusses important legal updates impacting Illinois landlords and rental property managers. Topics include upcoming 2025 legal updates to evictions, leases, notices, and more. (58 mins.)

“Chicago and Illinois Landlords: Preparing for an Eviction” – KSN landlord/tenant attorney Jessica Ryan discusses important legal updates impacting Illinois landlords and rental property managers. Topics include adhering to updated laws (federal and state plus local ordinances), landlord responsibilities, notices, liability, potential violations, and more. (65 mins.)
“Termination Notices for Illinois and Chicagoland Landlords” – KSN landlord/tenant attorney Jessica Ryan discusses important legal updates impacting Illinois landlords and rental property managers. Topics include evictions, proper termination notices, legal requirements, and more. (61 mins.)
“The State of Post-Pandemic Evictions: Where Are We Now?” – KSN landlord/tenant attorney Jessica Ryan discusses important legal updates impacting Illinois landlords and rental property managers. Topics include the CARES Act, Cook Counties Early Resolution Program (ERP), rental assistance, and more. (64 mins.)
“Chicago and Cook County Landlord Laws – Comparing the RLTO and RTLO” – KSN landlord/tenant attorney Jessica Ryan discusses important legal updates impacting Illinois landlords and rental property managers. Topics include the Residential Tenant Landlord Ordinance (RTLO), Residential Landlord Tenant Ordinance (RLTO), local ordinance comparisons (Oak Park, Evanston, Mount Prospect), and more.(55 mins.)
“2024 Illinois Landlord Legal Updates – Part 2” – KSN landlord/tenant attorney Jessica Ryan discusses important legal updates impacting Illinois landlords and rental property managers. Topics include the Just Housing ordinance, Cook County Residential Tenant Landlord ordinance, source of income, state of evictions, and more. (50 mins.)
“2024 Illinois Landlord Legal Updates – Part 1” – KSN landlord/tenant attorney Jessica Ryan discusses important legal updates impacting Illinois landlords and rental property managers. Topics include changes to accepting electronic rent payments, updates to Fair Housing, electric vehicle charging, Illinois Tenant Radon Protection Act, and more. (60 mins.)
“Illinois Fair Housing Act and Discrimination: Legal Issues Impacting Chicagoland Landlords and Rental Property Managers” – KSN landlord/tenant attorney Jessica Ryan and Laura Boggioni discuss the Illinois Fair Housing Act and Discrimination. Topics include affects on tenants, Section 8 housing vouchers, screening, inspections, property management, and more. (55mins.)
“Landlord Frequently Asked Questions Part 2” – KSN landlord/tenant attorney Jessica Ryan discusses frequently asked questions by Chicagoland landlords and rental property managers. Topics include evictions process, legal concerns, serving a tenant proper notice, accepting partial rent payments, unpaid balance options, and more. (48 mins.)
“Landlord Frequently Asked Questions Part 1” – KSN landlord/tenant attorney Jessica Ryan discusses frequently asked questions by Chicagoland landlords and rental property managers. Topics include emotional support animals, move-in fees, security deposits, updated Illinois regulations regarding electric vehicle charging, lease violations, and more. (46 mins.)
“Just Housing Ordinance & Criminal Background Screening” – KSN landlord/tenant attorney Jessica Ryan discusses the Just Housing Ordinance & criminal background screening in Chicagoland and Illinois residential rentals. Topics include adhering to updated laws (federal and state plus local ordinances), landlord responsibilities, liability, potential violations, and more. (51 mins).

“Evictions: Common Mistakes” – KSN landlord/tenant attorney Jessica Ryan discusses common mistakes in residential rental evictions. Topics impacting landlords and rental property managers include adhering to updated laws (federal and state plus local ordinances), landlord responsibilities, notices, liability, potential violations, and more. (57 mins)

“2023 Illinois Landlord/Tenant Legal Updates” – KSN landlord/tenant attorney Jessica Ryan discusses the addition of source of income as a protect class to Illinois Fair Housing law and the impact on Chicagoland and Illinois landlords. Jessica reviews how this legal update affects tenants, Section 8 housing vouchers, screening, inspections, property management, and more. (52 mins.)
“Chicago Residential Landlord and Tenant Ordinance” – KSN landlord/tenant attorney Jessica Ryan discusses the Chicago Residential Landlord and Tenant Ordinance (RLTO). She reviews what steps need to be followed to be in compliance with this Chicago ordinance. (54 mins.)

“Cook County Residential Tenant Landlord Ordinance” – KSN Attorney Jessica Ryan discusses the Cook County Residential Tenant Landlord Ordinance (RTLO) and what steps need to be taken in order to be compliant with the ordinance. (60 mins.)

“Laws Affecting Rental Properties In Illinois” – KSN attorney Jessica Ryan discusses important laws affecting rental properties, legal updates including evictions, notices, tenant screening, and more. (49 mins.)

Publications

KSN Blog: Understanding Abandonment in Illinois Rental Properties
KSN Blog: Update to Illinois Fair Housing Law Effective January 2023: Impact on Illinois Landlords
KSN Blog: How Does the New Cook County Landlord Ordinance Impact Landlords?
KSN Blog: How the New Fair Debt Collection Practices Act Rule Impacts Landlords
KSN Blog: Breach of Contract: A Landlord’s Beacon of Hope
KSN Blog: Case Update: Wing Street CA v. Kiss the Chef, LLC
KSN Blog: HUD Issues New Guidelines on the Use of Criminal Records in Rental Applications
KSN Blog: Chicago Adopts Home Sharing Ordinance
KSN Blog: Appellate Court Rules In Favor Of Association To Recover Unpaid Assessments From Third-Party Purchaser
KSN Blog: A Landlord’s Trial Testimony Made Simple
KSN Blog: Unmasking Opportunities in Foreclosures
KSN Blog: Service vs. Posting: What’s the Difference?
KSN Blog: Associations as Landlords: Evictions
KSN Blog: A Landlord’s Five-Day Notice: The Who, What, When, and How
Quoted in “Should I let my tenant post their unit on short-term rental sites like Airbnb and VRBO?” (2022, Story by JP Morgan)
Quoted in “Thinking about investing in short-term rentals? Here’s what to know.” (2022, Story by JP Morgan)
3rd Quarter 2014: Co-author, “Assessing the Value of a Property Tax Appeal: Worth it or Not?”, APTitudes Magazine.
March 2014: “Illinois Finally Pulled the Trigger on Concealed Carry”, National Apartment Association, Apartment Holdings.
1st Quarter 2014: “New Illinois Legislation: Key Issues”, APTitudes Magazine.
December 2013: “Medical Marijuana: Are Association Rules going Up in Smoke?”, KSN Blog:
March 2010: Quoted in “Tips on getting delinquent owners to pay up”, Chicago Tribune.
Spring 2009: “Unmasking Opportunities in Foreclosures”, Common Interest Magazine.

Speaking

Straight Up Chicago Investor Podcast episode 193 – “The 2023 Guide to The Chicago Eviction Process” (2023)
Straight Up Chicago Investor Podcast episode 143 – “Ins and Outs to Navigating Chicago Short-Term Rentals” (2022)
2013 – 2020: Presenter, “Crime Free Housing” Seminar, Mount Prospect Police Department.
August 2021: Presenter, “Expiring Eviction Moratorium” Webinar, KSN.
July 2021: Presenter, “Illinois Eviction Moratorium Set to Expire.” WGN-TV Political Report. Chicago.
June 2021: Presenter, “Cook County RTLO Compliance and Implementation” Webinar, Chicagoland Apartment Association.
May 2021: Presenter, “Rental Housing Law Review 2021: Overview of Landlord-Tenant Ordinance for Chicago and Cook County” Webinar, CIC.
April 2021: Presenter, “Cook County RTLO” Webinar, KSN.
January 2021: Presenter, “Landlord Tenant Legal Updates” Webinar, KSN.
December 2020: Presenter, eviction moratorium and landlord/tenant legal updates, Chicagoland Apartment Association.
June 2020: Presenter, Local Legal Update, National Apartment Association.
May 2020: Presenter, Local Legal Update, Chicagoland Apartment Association.
May 2020: Presenter, Local Legal Update, Community Investment Corporation.
April 2019: Presenter, “22.1 Disclosures” Seminar, Community Association Institute, Illinois Chapter.
November 2013 – 2017: Presenter, “Crime Free Housing” Seminar, Mount Prospect Police Department.
February 2018: Presenter, “The Chicago RLTO: An Overview” Seminar, Community Investment Corporation.
January 2018: Presenter, “The Chicago RLTO: Avoiding Pitfalls and Liability” Webinar Series, National Apartment Association.
June 2017: Presenter, “The Chicago RLTO: An Overview” Seminar, Community Investment Corporation.
May 2017: Presenter, “Crime Free Housing” Seminar, Wheeling Police Department.
April 2017: Presenter, “The Chicago RLTO” Seminar, Chicago Housing Authority.
April 2017: Presenter, “The Chicago RLTO: Avoiding Pitfalls and Liability” Webinar, KSN.
October 2016: Panelist, “Retaining Your Best Tenants: Keeping Residents Safe, Happy, and Ready to Renew” Panel, Chicago Housing Authority Owner Symposium.
May 2016: Presenter, “Disparate Impact and Criminal Background Checks” Seminar, Rogers Park Builders Group.
February 2016: Presenter, “CAA Legal Update 2016”, Chicagoland Apartment Association.
May 2015: Presenter, “Security Deposits” Webinar, KSN.
February 2014: Presenter, “Association Legal Update”, Naperville Area Homeowners Confederation.
September 2013: Presenter, “Navigating the Eviction Process”, Chicago Housing Authority Owner Symposium.
July 2013: Presenter, “Foreclosures and Bankruptcy” Webinar, KSN.
May 2013: Presenter, “Evictions and Problem Tenants” Seminar, National Association of Rental Property Managers.
April 2013: Presenter, “The Fundamental Five for 2013: Hot Topics You Need to Know” Seminar, Chicagoland Apartment Association.
January 2013: Presenter, “Mock Trial” Presentation, Community Association Institute.
October 2013: Presenter, “Bedbugs: Tiny Pests That Create Huge Problems in Multi-Family Housing” Webinar, KSN.
September 2012: Presenter, “Navigating the Eviction Process” Seminar, Chicago Housing Authority Owner Symposium.
February 2012: Presenter, “Collections and Foreclosure in Condominium Associations” Seminar, Chicago Bar Association Young Lawyers Section, Real Estate Committee.
January 2012: Presenter, “Racing the Banks: Association Collections in the Foreclosure Crisis” Webinar, KSN.
April – June 2010: Presenter, “Securing the Financial Future of Your Association” Seminar Series.
April 2010: Presenter, “Making Your Association Marketable: The New FHA Guidelines” Seminar, Dundee Public Library.
March 2010: Presenter, “Association Strategies in Today’s Economy” Seminar, Joliet Public Library.
February 2010: Presenter, “How Not To Collect Assessments”, CAI-Illinois Conference and Trade Show.

Awards

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