U.S. Route 20 (US 20) in the U.S. state of Illinois is a major arterial highway that runs from the Iowa state line at East Dubuque at the northwestern tip of Illinois to the Indiana state line at Chicago south of the Chicago Skyway, a distance of 233.93 miles (376.47 km). For its entire length, US 20 is designated as the General Ulysses S. Grant Highway, often abbreviated the U.S. Grant Memorial Highway. However, this name is only commonly used west of Elgin. US 20 bypasses the city of Elgin on a freeway known as the Elgin Bypass or Dr. Martin Luther King Jr. Memorial Highway. From Elgin to Melrose Park, US 20 follows Lake Street. It then follows Mannheim Road and, further south, La Grange Road. US 20 also follows 95th Street as it turns east through Chicago's southwestern suburbs. It ultimately leaves Illinois on Indianapolis Boulevard.

Interstate 90 (I-90) in the US state of Illinois runs roughly northwest-to-southeast through the northern part of the state. From the Wisconsin state line at South Beloit, it heads south to Rockford before heading east-southeast to the Indiana state line at Chicago. I-90 traverses 124 miles (200 km) through a variety of settings, from farmland west of the Fox River Valley through the medium-density suburbs west of O'Hare International Airport, through Downtown Chicago, and through the heart of the industrial southeast side of Chicago before entering Indiana.