[a] The system opened in 1958 in the Chicago area, and has subsequently expanded to include the eastern and central sections of Interstate 88 (I-88) extending into the northwestern part of the state.

The first segment to open was the Jane Addams Memorial Tollway between Devon Avenue and Elgin on August 20, 1958 at 3 p.m.[7] The Toll Highway Act, in its present form, dates from 1967, but has been amended since.

[8] Under this Act, promulgated April 1, 1968, ISTHA assumed the assets and obligations of the Illinois State Toll Highway Commission.

[10] Officials at the Morton Arboretum, one of the nation's premier woodland research centers, promptly filed a federal lawsuit to block construction of the tollway.

I-355 was extended south of I-55 to connect to I-80 in New Lenox, a distance of 12.5 miles (20.1 km), in order to serve fast-growing areas of Will County.

The Authority has the power to collect and raise tolls, and is responsible for the maintenance and construction of tollway roads and related signage (including electronic message boards, used for driving time notices, Amber Alerts and other notifications).

The close relationship between the governor and the near-majority of appointed board members has led to numerous allegations of endemic corruption throughout the tollway authority's lifetime.

[30] ISTHA also operates a fleet of Highway Emergency Lane Patrol vehicles which assist stranded motorists with mechanical problems, flat tires or insufficient fuel.

[31] As of 2017[update], ISTHA maintains and operates 306 miles (492 km) of tollways in 12 counties in northern Illinois, comprising five routes: Except for the vicinity of O'Hare International Airport, none enter the city of Chicago.

On January 1, 2012, tolls increased by 87 percent, to 75 cents at the main plazas for transponder-equipped cars, and $1.50 for those paying cash.

Illinois Tollway offers an auto-pay replenishment option by registering a credit or debit card to an I-Pass account at the time of activation.

[39] Users choosing to replenish their account without auto-pay are responsible for monitoring their transactions and balance and must pay a $20 refundable deposit.

Original plans for this toll highway would have seen it constructed through the middle of land belonging to the Arboretum, and closer to the existing Illinois Route 53.

The original decision to build the tollway was made in an era when five states used toll roads to create a superhighway between New York and Chicago.

[43] Citizens' groups formed in the 1990s to try to force ISTHA to disband, and convert the toll highways in Illinois into freeways.

The Sierra Club criticized the capital projects as adding to urban sprawl while hurting air quality.

[48] In response, the expense of implementing Open Road Tolling has justified by claiming it significantly decreases the amount of pollution from vehicle exhaust that enters the air.

This is because the old barrier style tollbooths adds to the amount of time that certain vehicles spend on the roadway by requiring them to slow down, stop, and sometimes idle for several minutes while waiting to pay their tolls.

[49] In 2003, during Governor George Ryan's administration, ISTHA entered into a public-private partnership with Wilton Partners to renovate the oasis rest stops in exchange for a 25-year lease.

[50][51][52] On December 9, 2008, Governor Blagojevich was arrested on corruption charges including allegations that he solicited campaign donations from Tollway construction contractors.

[53] On December 18, Dalley resigned claiming that Illinois Attorney General Lisa Madigan would not grant waivers from the state ethics law that prohibited high level ISTHA executives from being employed by contractors within a year of leaving office.

[52] On August 12, 2009, John Mitola, who was appointed the ISTHA board chairman in 2003 by Governor Blagojevich, resigned for personal reasons.

[52] Ex-ISTHA Chairman Mitola was reported to have failed to disclose an investment in a real estate development with former state purchasing and contracting CEO Michael Rumman under ousted Governor Blagojevich.