How to Travel From Chicago to Milwaukee by Train, Bus, Car, and Plane

TripSavvy / Julie Bang

Traveling from Chicago, Illinois to Milwaukee, Wisconsin is relatively simple as the two cities are only 93 miles apart. There are many ways to get from Chicago to Milwaukee and there are pros and cons for each mode of transportation.

While you can fly from one city to the next, the overall travel time will be quite lengthy when you factor in getting to the airport and waiting for your one-hour flight to take off. Plus, flights are more costly than traveling by train, bus, or by driving. Taking the bus is an option, but it will take around two hours from point A to point B, depending on traffic, and might not be as comfortable as a car or train. If you have to rent a car for the trip, you’ll have to factor in the extra costs, including gas and tolls, and traffic will be a concern. The Amtrak train, an optimal option, is smooth, quiet, and clean and will get you to Milwaukee in 90 minutes. You'll also have to consider options for getting around Milwaukee if you don't have a car; public transportation is a great resource.

How to Get from Chicago to Milwaukee

  •      Train: 1 hour, 29 minutes, from $27 (fastest)
  •      Flight: 59 minutes, from $200 (most expensive)
  •      Bus: 2 hours, 20 minutes, from $11
  •      Car: 1 hour, 29 minutes, 93 miles

By Train

Amtrak is a great option, perhaps the best, for traveling from the biggest city in Illinois to the biggest city in Wisconsin. Trains operate every two to four hours and tickets cost between $27 and $40, depending on route, operator, and distance traveled. You’ll travel from Chicago Union Station to Milwaukee Intermodal Station. You can track your train, book and store purchased tickets, and receive travel advice on your smart device via the free Amtrak mobile app. Tickets may also be purchased online or in-person at Union Station.

The biggest advantage of traveling by train is that it’s quick, inexpensive, comfortable, and direct. You won’t have to worry about traffic or driving in inclement weather and if you’re traveling with friends or loved ones, you can socialize instead of paying attention to the rules of the road.

By Bus

Taking the bus is an affordable option for traveling from one city to the next but it is also the mode of transportation that will take the longest, depending on traffic and weather. Travel times vary and range from one hour and 45 minutes to two hours and 40 minutes.

The Greyhound bus station is located at the Chicago Amtrak Bus Station in Chicago Union Station, located at 225 S. Canal Street. You can also take a Megabus which operates with up to four services per day, costs $24.99, and takes around two hours.

The pros of bus travel are that multiple departure times exist, even at night, and the fares are relatively inexpensive. Plus, you’ll have free Wi-Fi onboard, and you can utilize power outlets to charge your devices.

By Car

Traveling by car is one of the best, and least expensive, ways to get from the Windy City to the Cream City. It will behoove you to follow the rules of the road and pay attention to traffic, timing, and road etiquette. Hop on I-90/I-94 west and it’s pretty much a straight shot north, along Lake Michigan. En route, you’ll pass Des Plaines, Riverwoods, and Gurnee in Illinois before you cross state lines, and then you’ll travel through Kenosha and Racine before reaching Milwaukee.

You can expect to pay between $9 to $14 in gas and tolls will cost between $2.35 and $4.70, depending on whether you pay in cash or have a transponder like the I-PASS or E-Z Pass. Parking can be easily found in Milwaukee, especially if you’re visiting a venue or hotel.

There are several advantages to traveling via car. You can go at your own pace, pack as much gear and clothing as you like, and you’ll have an automobile to get around in when you’ve reached Milwaukee. Having a vehicle, when you have kids in tow, is also a big pro. The cost of travel is much lower compared to other forms of transportation when you consider how many passengers are along for the ride.  

By Plane

Flights from Chicago O’Hare International Airport (ORD) or Chicago Midway Airport (MDW) leave for Milwaukee throughout the day, every day, serviced by United Airlines and American Airlines. Flights are about one hour, and the pricing varies.

The drawback to flying from city to city is that it is the most expensive way to travel and the most time-consuming. You have to factor in the time it takes to get to the airport—either by public transportation or ride share—check in, and wait for your flight to board. ORD is 18 miles from Chicago’s Loop and MDW is 11 miles away. From the Loop, travel times are 50 minutes to ORD on Chicago Transit Authority’s (CTA) Blue Line or 37 minutes to MDW via CTA’s Orange Line.

What to See in Milwaukee

From seasonal events and festivals to macro and micro-brewery tours to casinos to venues that draw big musical acts, Milwaukee has a lot to offer every visitor. Plus, the city is changing and constantly refreshing its look. There’s a shiny new sport’s arena (Fiserv Forum, where the Milwaukee Bucks play basketball), plenty of retail spaces that are opening their doors on the regular, and new and renovated hotels. The Kimpton Journeyman Hotel opened in 2016 and The Westin Milwaukee opened in 2017. New restaurants and markets in the city include Sherman Phoenix, Crossroads Collective, Uncle Wolfie’s Breakfast Tavern, and La Merenda Marketplace.

Visit with your family or friends to see the Milwaukee County Zoo, Milwaukee Art Museum, or the Harley-Davidson Museum. Take your significant other to The Pabst Mansion, Milwaukee Riverwalk District, or to a Brewers game at Miller Park. 

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