Next departures for Milwaukee to Chicago on November 15
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Train
MKE Airport - Trains
Chicago (Union Station), IL
CheapestFastest
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
Intermodal Station
Chicago (Union Station), IL
No tags
Train
Intermodal Station
Chicago (Union Station), IL
No tags
Next departures for Milwaukee to Chicago on November 16
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Train
MKE Airport - Trains
Chicago (Union Station), IL
Cheapest
Train
MKE Airport - Trains
Chicago (Union Station), IL
Fastest
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Next departures for Milwaukee to Chicago on November 17
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Train
MKE Airport - Trains
Chicago (Union Station), IL
CheapestFastest
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Next departures for Milwaukee to Chicago on November 18
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Train
MKE Airport - Trains
Chicago (Union Station), IL
CheapestFastest
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Next departures for Milwaukee to Chicago on November 19
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Train
MKE Airport - Trains
Chicago (Union Station), IL
Cheapest
Train
MKE Airport - Trains
Chicago (Union Station), IL
Fastest
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Next departures for Milwaukee to Chicago on November 20
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Train
MKE Airport - Trains
Chicago (Union Station), IL
Cheapest
Train
MKE Airport - Trains
Chicago (Union Station), IL
Fastest
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Next departures for Milwaukee to Chicago on November 21
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Train
MKE Airport - Trains
Chicago (Union Station), IL
Cheapest
Train
MKE Airport - Trains
Chicago (Union Station), IL
Fastest
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Next departures for Milwaukee to Chicago on November 22
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Train
MKE Airport - Trains
Chicago (Union Station), IL
CheapestFastest
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Train
MKE Airport - Trains
Chicago (Union Station), IL
No tags
Last refresh of the prices: Today at 8:22 AM CST.
Compare 2 ways to go from Milwaukee to Chicago
We recommend taking the train
Among the sustainable travel choices, the train stands out as the good way to reach Chicago. The journey takes about 1 hour 29 minutes and with fares starting at just $23, it presents an excellent value for a comfortable ride.
Customers generally found the booking process straightforward and appreciated a pleasant, relaxing trip. They noted that bringing extra layers is advisable due to cold temperatures on board. Some mentioned minor issues such as delays caused by equipment problems and interactions with staff could be improved in certain situations.
Amtrak Milwaukee Chicago recent customer reviews
It was very relaxing and quiet had a great nap just didn’t like how cold It was but luckily I brought my sweater
5 out of 5 stars
Chamqual G.
The conductor was very personable. There was a 40 minute delay due to equipment issues
4 out of 5 stars
Jeffrey B.
It was very easy to book an e-ticket
The trip was pleasant there were no problems or issues
Frequently asked questions about traveling from Milwaukee to Chicago by train
How much does a train ticket from Milwaukee to Chicago cost?
The average train ticket price from Milwaukee to Chicago is $30. The best way to find train tickets from Milwaukee to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the train trip from Milwaukee to Chicago?
A train trip between Milwaukee and Chicago is around 1h 29m, although the fastest train will take about 1h 19m. This is the time it takes to travel the 84 miles that separates the two cities.
How many daily trains are there between Milwaukee and Chicago?
The number of trains from Milwaukee to Chicago can differ depending on the day of the week. On average, there are 15. Some trains are direct while others have layovers. Simplify your train trip from Milwaukee to Chicago by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from Milwaukee to Chicago?
When taking the train from Milwaukee to Chicago, you can travel comfortably and safely with Amtrak.
What are the best sights and things to do in Chicago?
Once in Chicago, you can explore the city. The top sights and things to do are Museum of Contemporary Art, Willis Tower (Sears Tower), Chicago Shakespeare Theater on Navy Pier, Navy Pier, Lincoln Park Zoo.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
11/13
$27
11/14
$30
Today
$27
11/16
$30
11/17
$23
11/18
$23
11/19
$23
11/20
$25
The cheapest trip from Milwaukee to Chicago was searched and found on Nov 17, 2025 with a price of $23
To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Milwaukee to Chicago, as early as possible.
You can expect to pay from $23 to $38 for a train ticket from Milwaukee to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $23 which is on 2025-11-17.
What's the cheapest way to go from Milwaukee to Chicago?
The train is the cheapest travel choice for this destination
The best way to travel between Milwaukee and Chicago is by train. By choosing the train, you'll get to save some money as you travel to your destination, as ticket prices cost $30 on average. If you're on a budget, you'll find cheap tickets from $23. If you're looking for the fastest way to get to Chicago, choose the train, as it will take you from Milwaukee to Chicago in about 1h 29m - that's the fastest way to get there!