Driving to Chicago from the north, south, east, or west is very easy given that Chicago is a Midwestern hub and several major interstates connect right in Chicago's downtown. Here's how to get to Chicago by car depending on which direction you're coming from.
From the East: When traveling from the east, the best route is to take I-80. Once crossing into Indiana, I-80 merges into the I-90/Chicago Skyway, which in turn feeds into the I-94/Dan Ryan Expressway which goes directly into downtown. Travelers starting out from points further northeast can take I-90 the entire way to I-94.
From the West: I-80 is the most direct route coming from the west as well -- it stretches all the way to California. When you're approximately 150 miles from Chicago, I-80 merges onto I-88. Continue following I-88 and it becomes the I-290/Eisenhower Expressway, which also leads directly downtown.
From the North: I-94 is the way to go when traveling from parts north, like Minneapolis. Once I-94 reaches Madison, Wisconsin, it heads due east towards Lake Michigan where it turns south towards Chicago, eventually feeding into the I-90/Kennedy Expressway, which -- once again -- leads directly downtown.
From the South: I-55 is the interstate of choice for drivers coming to Chicago from places like Memphis or New Orleans. Once I-55 reaches Illinois, it mainly follows the direction of the famous Route 66. I-55 can be taken all the way into Chicago, where it ends at Lake Shore Drive in front of Soldier Field.