Getting from Milwaukee to Chicago

Milwaukee and Chicago are about 90 miles apart, close enough that plenty of people do the trip as a day out. The train is the best way to do it, and it isn't close. The bus is cheaper, and driving makes sense if you're going somewhere the L doesn't reach. Flying is only for connections.

By train

Amtrak's Hiawatha is one of the best short train rides in the Midwest. It makes six round trips a day (five on Sunday), and the ride takes about an hour and a half, faster than most drives at rush hour (Wikipedia). Trains leave from the Milwaukee Intermodal Station at 433 W. St. Paul Ave. downtown and stop at Milwaukee Airport, Sturtevant and Glenview before Chicago Union Station. Every train has a quiet car, and there's a Business Class car if you want a bigger seat.

The daily Borealis runs the same line with the same stops, on its way between Chicago and St. Paul, so it gives you one more departure each way. It started in 2024 (Wikipedia). Between them, the first train leaves Milwaukee in the early morning and the last one leaves Chicago late in the evening, with a later train on Fridays. Check the Amtrak timetable for times.

A few tips. The Milwaukee Airport station isn't in the terminal. It's about three-quarters of a mile away, and a free shuttle runs between the station and baggage claim. The Chicago Union Station stop is on Canal Street on the west side of the Loop, a short walk from the Blue Line and the Loop L. Fares go up as trains fill, so book early for Brewers-Cubs weekends and holidays.

One more option, if you're coming from Kenosha or south of Racine. Metra's Union Pacific North Line runs from Kenosha to Ogilvie Transportation Center downtown, though only some trains go all the way to Kenosha (Metra). It's a commuter train, slower than the Hiawatha, but you don't need a reservation.

By bus

FlixBus and Greyhound, which Flix owns, run several buses a day from the Milwaukee Intermodal Station, the same building as the train, and some FlixBus trips also stop at Mitchell Airport. Most end at the Greyhound station at 630 W. Harrison St. in Chicago, close to the Blue Line's Clinton stop. Some stop at the Cumberland Blue Line station near O'Hare instead. The ride takes about an hour and a quarter to two and a quarter hours, depending on the run and traffic. Fares are usually lower than the train, which is the main reason to take the bus.

If you're flying out of O'Hare, look at Coach USA's Airport Express. It runs daily from stops around southeast Wisconsin and Mitchell Airport to O'Hare.

Megabus, the cheap double-decker that used to run this route, isn't the same business now. After its parent went through bankruptcy in 2024, megabus.com became a booking site for other bus lines. Milwaukee tickets sold there are on partner buses, so check which company and stop your ticket names.

Driving

It's about 90 miles, almost all on I-94. Figure on an hour and a half to two hours without heavy traffic, and a lot longer on a weekday rush hour or a summer Friday afternoon. The road from the state line into the city is the Tri-State Tollway, and Illinois tollways don't take cash. An I-PASS or E-ZPass works, or you can pay online with the Illinois Tollway after the trip. Closer in, I-94 becomes the Edens and then the Kennedy, which backs up at almost any hour.

Downtown parking is expensive, and hotel valet costs even more. If you're only in town for a day, drive to the Hiawatha instead, or park near an outlying L station and ride in. See our getting to Chicago page for more on driving and parking in the city.

Flying

American Eagle and United Express fly from Milwaukee Mitchell to O'Hare, and Southwest flies to Midway (Wikipedia). Those flights are for connecting to somewhere else, not for getting to Chicago. With check-in and security, a flight takes longer door to door than the train. See our airports page for O'Hare and Midway.

If you're making the trip in the other direction, see our page on things to do in Milwaukee.

Photo by magrolino