“Chicagoland” refers to the expansive metropolitan region surrounding Chicago, encompassing the city’s urban core as well as parts of northeastern Illinois, northwestern Indiana, and occasionally southeastern Wisconsin. This region is home to countless midwesterners, many of whom commute into downtown Chicago, whether occasionally or daily. A well-connected network of major highways makes traveling and commuting throughout Chicagoland convenient and efficient. Whether you’re a longtime local or new to the area, here’s an overview of the key highways you should know.

I-90 (Kennedy Expressway)

Interstate 90 in Chicago is part of the extensive I-90 system, the longest interstate highway in the United States, stretching from Boston to Seattle. In Illinois, I-90 spans 124 miles, weaving through farmland, suburbs, industrial zones, and downtown Chicago. Within the Chicago area, I-90 is divided into four distinct sections:

Chicago Skyway: A toll bridge located on the city’s southeast side.
Dan Ryan Expressway: A major north-south route that carries both I-90 and I-94.
Kennedy Expressway: Another segment that also includes both I-90 and I-94.
Jane Addams Memorial Tollway: The portion west of Chicago, often referred to as the Northwest Tollway.

Together, these sections connect diverse parts of Illinois, serving as a vital artery for travel and commerce.

I-290 (Dwight D. Eisenhower Expressway)

Interstate 290, commonly known as the “Ike,” is a vital east-west freeway connecting Chicago’s Loop to the city’s western suburbs. Starting at the Jane Byrne Interchange in downtown Chicago, the highway stretches westward, serving as a critical route for commuters traveling to and from the city’s central business district. Officially named the Dwight D. Eisenhower Expressway, the road’s nickname pays homage to its namesake, though many locals simply call it “the Eisenhower.” As a key corridor, I-290 plays an essential role in facilitating daily travel throughout the region.

I-94 (Bishop Ford Memorial Freeway)

I-94 is a major east-west highway running through Chicago, seamlessly connecting the Kennedy Expressway, the Dan Ryan Expressway, and the Bishop Ford Memorial Freeway. For part of its route, it merges with I-90 along the Kennedy and Dan Ryan sections. Entering Illinois from the Wisconsin border, I-94 travels through downtown Chicago before continuing into Indiana. A small stretch of the highway, located on the Tri-State Tollway just north of Chicago, is subject to tolls. North of the tollway, the highway’s final segment within Illinois is known as the Edens Expressway.

I-294 (Tri-State Tollway)

Interstate 294, an extension of I-94, is a toll highway that serves northeastern Illinois. Known as the southern section of the Tri-State Tollway, it stretches from South Holland—where I-80 and I-94 intersect—to Northbrook at I-94. This route passes through the Chicago Panhandle, providing a critical connection between Chicago O’Hare International Airport and the rest of the city.

As it continues, I-294 enters Rosemont, passing beneath I-190, Balmoral Avenue, and the Blue Line “L” tracks. The highway also offers convenient access to major roadways, including I-90, making it a vital thoroughfare for travelers and commuters alike.

To pay tolls on I-294, drivers must use an electronic transponder or opt for the pay-by-plate system, which bills users by mail. Traditional payment methods, such as cash and credit cards, are no longer accepted at toll plazas—a change implemented to reduce congestion and improve traffic flow.

I-55 (Adlai E. Stevenson Expressway)

Interstate 55 closely follows the historic route of US Route 66 and is officially designated as the Adlai E. Stevenson Expressway. Starting at Lake Shore Drive in Chicago, it winds southwest through key Illinois suburbs like Joliet, Bloomington, and Springfield, eventually connecting to St. Louis and beyond. As a major north-south artery, I-55 is essential for Illinois commuters, providing a vital link for daily travel into the city.

A section of I-55, stretching from the southern suburbs to near Pontiac, has been renamed the Barack Obama Presidential Expressway. This honor recognizes the 44th president, whose political career began in Illinois. Before his presidency, Obama served as both a state senator and U.S. senator, leaving a lasting impact on the state he once called home.

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