1995: In 1995, the Chamber joined together with Lt. Governor Bob Kustra, the Illinois Department of Alcoholism and Substance Abuse, The Illinois State Chamber of Commerce and the Chicago Department of Health to expand the Drug-Free Workplace Program into the Drug-Free Illinois Workplace Program. The Chamber supported what proved to be passage of brownfields legislation and viewed it to be a great success for businesses and cities throughout the state. Moreover, the Chamber was the lead chamber in putting together the Chicago Area Health Alliance, in which both neighborhood and suburban chambers participated. In the same year, the Chamber fought and won a tough battle for tort reform in the Illinois legislature, the Chamber led the successful effort to reduce Chicago's Employee Head Tax, and the Chamber played a leading part in securing Chicago as the site of the 1996 Democratic Convention. Additionally, the Chamber was instrumental in passing legislation that gave Chicago’s Mayor governance and administrative control of Chicago Public Schools (CPS).

In addition to hosting a series of citywide meetings on Chicago Public School reform in 1996, the Chamber was instrumental in pushing the CPS agenda in Springfield, leading to the passage of school principal accountability legislation. This same year, the Chamber sponsored the August 5th Chicago appearance of Presidential Candidate Bob Dole, at which he revealed his tax and economic plan. U.S. Attorney Janet Reno was the keynote speaker for the Crime Prevention Awards Luncheon and commended Chicago for having the first and most effective community policing effort. The Luncheon also drew James Burns, U.S. Attorney for the Northern District of Illinois as well as Mayor Richard M. Daley in 1996. Meanwhile, freshman Congressman, Jesse Jackson Jr., was the keynote speaker at the 30th annual Youth Motivation Program recognition Luncheon.

Also in 1996 the Chamber developed the region's first labor management consortium, the Chicagoland Area Labor-Management Committee. The Chamber Subcommittee for Central Europe and Eurasia visited Romania and signed memoranda of cooperation with chamber executives in the cities of Galati and Bihor in 1996. These documents commit their chambers and the Chicagoland Chamber to sharing economic and business information that benefit respective members.

The National Chamber of Commerce in Poland visited Illinois and entered into a formal relationship with the Chicagoland Chamber, launching a chamber-to-chamber partnership.

The Chamber's Latin American Subcommittee signed an alliance with the Chamber of Commerce in San Cristobal, Dominican Republic.

Finally in 1996, the Chamber-backed Unemployment Insurance Tax reform bill was successfully signed by Governor Jim Edgar on February 8th.

The Chamber created a coalition of banks and governmental agencies to promote the FLAG (Financial institutions, Law enforcement And related Government agencies) program which protects the elderly and disabled from financial fraud in 1997. Also, the Chamber was among 11 business organizations in the Illinois Business Education Coalition that achieved major statewide education reform along with guaranteeing a foundation level of school funding.

In 1998, yearlong efforts by the Chamber-led Midwest Asia Aviation Coalition led to a treaty signing in early 1998 that added 22 non-stop O'Hare - Japan flights per week.

The Chamber also commissioned a 1998 study on O’Hare’s economic impact by Booz Allen & Hamilton. The report concluded that an O’Hare left in its current state of congestion and capacity would cost the region hundreds of thousands of jobs and billions of dollars per year in lost revenue.

Additionally, the Education Work Force Quality Committee recommended that the Board expand its school choice public policy to support school choice options that place a priority on improving the academic performance of those students who are the most educationally disadvantaged, presumably those in low income communities, and have the least choice.

The Chamber joined in 1999 with CTA, Yellow Cab, the Mayor's Office of Substance Abuse and the Illinois State Chamber in the first-ever Chicago safe holiday entertaining campaign, "Celebrate Smart." Also, the Croatian Chamber of Economy signed a co-operation agreement with the Chicagoland Chamber encouraging trade, investment, technical and economic cooperation between the Chamber and the Republic of Croatia. The Chamber hosted an Economic Conference on Trade and Business Opportunities in Croatia, in conjunction with the Croatian government as an integral part of the Presidential Trade and Business Mission this year as well.