As a Chicagoan, the pilgrimage to Milwaukee is a rite of passage. Compared to Chicago, Milwaukee is a change-of-pace city with a collegial vibe. Chicagoans descend upon Milwaukee en masse to enjoy the city’s bar, beer, and sports scene alongside its Lake Michigan beaches and sweeping Art Museum. From Chicago, Milwaukee is roughly a 90-mile drive and travel times range between two and four hours, depending on traffic counts and the time of day.
Driving Directions to Milwaukee: From Chicago
When driving to Milwaukee from Chicago, your ultimate goal is to merge with Interstate 94. Although I-94 follows a north-south geographical alignment between Milwaukee and Chicago, it will be signed as east-west. The east-west signage is due to the fact that 94 extends between Montana and Michigan across the Northern tier of America. For Milwaukee, you will therefore take I-94 West, which may also read as “Wisconsin” at some major junctions.
On the South Side, I-94 is referred to as the Dan Ryan Expressway. You can pick up the Dan Ryan heading west from the Chicago Skyway and off major numbered streets, such as 95th, 87th, 79th, 55th, and 47th streets. After the Skyway exits, The Dan Ryan is cosigned as I-90/94 as it barrels its way towards the Chicago Loop.
At the Loop, the Dan Ryan wraps around the Chicago skyline – with important interchanges at I-55 and I-290 alongside Roosevelt Road and the Ohio – Ontario feeders. North of downtown, I-90/94 transitions in the Kennedy Expressway and follows a northwest geographic alignment towards O’Hare Airport. On the North Side, you can pick up the Kennedy heading west for Milwaukee at IL 64/North Avenue, Fullerton Avenue, Belmont Avenue and IL 19/Irving Park Road.
After Irving Park Road, I-90/94 will divide at what locals refer to as “The Junction.” For 94 and Milwaukee, you will bear right onto the Edens Expressway. The Edens collects traffic on Chicago’s Far North Side and North Shore suburbs, before it meets the Tri-State Tollway in Northbrook. At the Tri-State, you will also bear right and follow signs for I-94 and Milwaukee. As of 2011, the Tri-State is a tolled route, and you will need $2.50 in cash as a passenger vehicle to make it to the Wisconsin border.
In Wisconsin, I-94 is six lanes across and a straight shot to Milwaukee. Be advised that this stretch of road is notorious for Wisconsin State Police that love to book Illinois drivers with speeding tickets.
Driving Directions to Milwaukee: From the Chicago – North Shore
From the North Shore, you will also look to pick up I-94 heading west (geographic north) for Milwaukee. On the North Shore, 94 traces the Edens Expressway and Tri-State Tollway within five miles of Lake Michigan. As a north suburbanite, you can merge onto 94 at major roads that include U.S. 41/Skokie Boulevard, IL 68/Dundee Road, and IL 22/Half Day Road. After joining the interstate, 94 heads directly into Southeast Wisconsin and the City of Milwaukee.
Driving Directions to Milwaukee: From Chicago – West and South Suburbs
From the west and south suburbs, you will link up with the I-294/Tri-State Tollway to bypass the City of Chicago and its notorious traffic. The 294/Tri–State forms a semi arc around Chicago through the suburbs of South Holland, Alsip, Elmhurst, Des Plaines, and Northbrook – with major interchanges at I-80, 55, 88, 290, and 90. For Milwaukee, you will take I-294 North, which is likely to be signed as “Wisconsin.”
In Northbrook, 294 ends and feeds into I-94 / Tri-State traffic. Once on I-94, you will follow this route west (geographic north) and into Milwaukee, Wisconsin.