Major highways of the Chicago region meet at the downtown core, so if your destination is elsewhere in the city it may be wiser to follow a different route. Freeways or expressways are usually referred to by name rather than by number by locals, especially in the city, less so in the suburbs.

• From the east (New York, Toledo, Detroit): Follow I-80/90 (Indiana Toll Road) or I-94 from Detroit. In Portage, IN, one can elect to stay on the toll road (I-90), which leads one to the Chicago Skyway toll bridge and thence to the Dan Ryan Expressway. Advantages include a slightly more direct route, slightly less traffic and a stunning view of the cityscape from atop the bridge. Disadvantage is the combined $3.50 passenger car toll. Otherwise, one can follow the Borman Expressway (I-80/94) which becomes the Kingery, then I-94 (Bishop Ford Freeway) to the Dan Ryan Expressway. This route, while free, is often plagued with traffic and is somewhat lengthier. See caution below about Dan Ryan construction.
• From the southeast (Indianapolis, Louisville): Take I-65 north to Gary, Indiana, then choose between alternatives mentioned above.
• From the south (Urbana, Memphis): Take I-57 north to its junction with I-94, follow I-94 (Dan Ryan) to downtown Chicago.
• From the southwest (Midway Airport, St. Louis, Tulsa): Take I-55 north (Stevenson Expressway) which ends at Lake Shore Drive just south of downtown.
• From the west (Des Moines, Omaha): Take I-80 east to I-55 or I-57 north, or I-94 west. Long-distance travelers may prefer taking I-88 (Reagan, ex-East-West Tollway), from the Quad Cities, then following I-290 (Eisenhower Expressway) into the city.
• From the northwest (O'Hare Airport, Madison, Minneapolis): Take I-90 east, the Northwest Tollway until the airport, the Kennedy Expressway thereafter, into the city.
• From the north (Milwaukee): Take I-94 west (actually mostly south), which is the Tri-State tollway for some miles, then the Edens Expressway until it merges with I-90 and becomes the Kennedy.

Major highways by name and number:

• I-55 (Stevenson Expressway): begins at Lake Shore Drive south of the Loop, travels southwest to Midway Airport, southwest suburbs and toward Saint Louis.
• I-57 (unnamed, sometimes labeled Dan Ryan Expressway, West Leg on older maps): Begins at I-94 south of 95th St, serves south suburbs, Urbana-Champaign and other Illinois communities.
• I-90: Enters the region as the Northwest Tollway, becomes the Kennedy Expressway then the Dan Ryan Expressway and then breaks off as the tolled Chicago Skyway, a link to the Indiana Toll Road.
• I-94: Enters the region as the Tri-State Tollway, then spurs off to become the Edens Expressway, meets I-90 and takes on its name (Kennedy Expressway), then follows the Dan Ryan Expressway and the Bishop Ford Freeway before meeting up with the Tri-State again and being known as the Kingery Expressway (in Illinois) and the Borman Expressway in Indiana.
• I-290 (Eisenhower Expressway) Runs straight west from downtown, serving West Side and western suburbs, then turns north to rejoin I-90 in Schaumburg.
• U.S. 41 (Lake Shore Drive) Mostly limited-access highway (but several stoplights downtown) with rewarding views of shore- and skyline. Posted speed limits (40-45mph) widely ignored.
• I-294 (Tri-State Tollway) Tolled beltway serving what are now middle-tier suburbs and a great deal of through truck traffic. Passes close to O'Hare.
• I-80 (Moline, then Kingery Expressway, with a segment in between on the Tri-State) While it doesn't serve Chicago proper, passes through south suburbs and links Chicago with points east (Toledo, Cleveland, New York...) and west (Des Moines, Omaha, San Francisco...).

-I-190 (Kennedy Expressway) Not really known as the Kennedy, this short spur provides access to O'Hare Airport's terminals.