This is the cheapest price found by a KAYAK user in the last 72 hours by searching for a train from Milwaukee to Chicago departing on 7/8. Fares are subject to change and may not be available on all trains or dates of travel. Click the price to replicate the search for this deal.
Round-trip
1 adult
Sat 7/12
Sat 7/19
Book train tickets from Milwaukee to Chicago
Here are some of the best deals found on KAYAK recently from the most popular providers for trips from Milwaukee to Chicago that are departing in the next months. While these deals were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Round-trip
One-way
Direct
Recent return train deals from Milwaukee to Chicago
Tue, Jun 24 - Thu, Jun 26
7:35 pm - 9:04 pmMilwaukee Intermodal- Chicago Union
1h 29mnonstop
6:10 am - 7:39 amChicago Union- Milwaukee Intermodal
Train tickets from Milwaukee to Chicago are on average 3% less expensive on Mondays
Train tickets from Milwaukee to Chicago are on average 2% more expensive on Tuesdays
(avg. price over the last 2 weeks)
(avg. price over the last 2 weeks)
Top tips for finding Milwaukee to Chicago train tickets
The most common departure and arrival stations for trains from Milwaukee to Chicago are Intermodal Station and Union Station. Intermodal Station is located just under a mile from downtown Milwaukee, with amenities including a waiting room, ATM, payphones, restrooms, vending machines, and a ticket sales office. In addition, the station offers checked baggage service and storage, and the staff provides baggage assistance service. Other amenities include wheelchairs and wheelchair lifts. Union Station in Chicago has a waiting room, restrooms, payphones, vending machines, and wheelchairs. You can access elevators and Amtrak Wi-Fi there as well.
When you book a train ticket from Milwaukee to Chicago through KAYAK, you can compare round-trip and single-ticket fares to get the best possible deal. Although unusual, it's possible to find two one-way tickets for less than a round-trip ticket. Try searching for different departure dates and times of day to find a ticket that best fits your budget.
We recommend thinking about the class of service you’d like onboard a train from Milwaukee to Chicago before purchasing your ticket. For instance, Amtrak from Milwaukee to Chicago offers services in coach and business class. Coach class has comfortable seats, at-seat lighting, tray tables, and ample legroom. On the other hand, business-class features more legroom, adjustable footrests, electrical outlets, and complimentary non-alcoholic drinks. Another factor to consider when choosing your seat class is whether your pet will tag along, as pets can't travel in business class on trains from Milwaukee to Chicago.
Flexible travel dates and times will allow you to find cheap train tickets for your trip. You should be ready to travel when the best deals are available on trains from Milwaukee to Chicago. Usually, that involves weekday travel when fewer people travel, particularly on Wednesdays. Therefore, you might want to forego traveling during busier times, such as weekends and holidays.
25% of our users found round-trip train tickets from Milwaukee to Chicago for $44 or less.
You will generally catch the best train deals if you travel in the afternoon.
The cheapest train from Milwaukee to Chicago was found 58 days before departure, on average.
FAQs when traveling from Milwaukee to Chicago by train
Is free Wi-Fi available on trains from Milwaukee to Chicago?
Yes, the Hiawatha Service route from Milwaukee to Chicago offers complimentary Wi-Fi, enabling you to work or check your email in transit. However, you might be unable to perform high bandwidth acts such as streaming music and videos. Free Wi-Fi is also available at your destination train station, Union Station in Chicago.
What are the luggage limits on trains from Milwaukee to Chicago?
While amenities vary by train, you can board with two personal items weighing up to 25 pounds and two carry-on items up to 50 pounds at no cost. It's worth noting that not all trains offer checked baggage service, but if your train from Milwaukee to Chicago allows it, you can check in two bags for free and two additional for roughly $20 each; each bag must weigh 50 pounds or less.
Are there business-friendly amenities onboard trains from Milwaukee to Chicago?
Yes, all Hiawatha trains journeying from Milwaukee to Chicago have a Quiet Car, which provides a quiet workspace for business travelers. Note that seats in the Quiet Car are on a first-come, first-served basis, so it's best to grab one early if you'll need to work. Seats in this section also have reading lights and outlets to power your devices and stay connected.
Are trains from Milwaukee to Chicago pet-friendly?
Yes, your small cat or dog can accompany you on your train ride, as long as it's in a pet carrier. However, the total weight of the pet and carrier shouldn't be more than 20 pounds. Only one pet per person is allowed, and you'll be required to purchase a pet transit fee for roughly $26. Pets can only travel in coach class on this route. Your train from Milwaukee to Chicago can only carry five total pets in one trip, so it's best to make your pet reservation early.
How long is a train journey to Chicago from Milwaukee?
The train journey from Milwaukee to Chicago takes 1h 30m on average and covers a distance of 81 miles.
What train companies travel from Milwaukee to Chicago?
Amtrak is the only train operator serving this route.
Search Chicago trains on KAYAK. Find cheap train tickets to Chicago from Milwaukee. KAYAK searches hundreds of travel sites to help you find cheap train fares and book the train that suits you best.
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