This is the cheapest price found by a KAYAK user in the last 72 hours by searching for a train to Chicago departing on 9/24. 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
Fri 10/17
Fri 10/24
Book train tickets to Chicago
Here are some of the best deals found on KAYAK recently from the most popular providers for trips 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.
Train tickets to Chicago are on average 18% less expensive on Saturdays
Train tickets to Chicago are on average 11% more expensive on Tuesdays
(avg. price over the last 2 weeks)
(avg. price over the last 2 weeks)
Top tips for finding Chicago train tickets
If you’re taking a train to Chicago, Union Station is the only train station in the city offering regional transit. All trains connecting with other cities in the United States and Canada leave from and arrive here. Get to and from Union Station using the CTA train system. It’s a great way to get around the city and the CTA Quincy stop is just half a mile away from the train station.
When visiting Chicago, look up train tickets to Union Station in Chicago instead of arriving by plane. It’s probable this option is more affordable than flying in to the city. Not only is it more likely to be more inexpensive, but when arriving in Chicago you’ll find that the Union train station is already downtown. Arriving at Union Station can make getting around the city and to wherever you may be staying easier and avoids any airport hassle.
If you’re taking the Amtrak to Chicago Union Station and you require accessible options of getting around, you have nothing to worry about. Chicago Union Train Station has an accessible entrance available at the main entrance on Canal Street. The station also offers elevators to get to the concourse from street level as well as assisted waiting and boarding areas in case you require extra assistance to get on or off the train.
A great idea for traveling by train is taking a day trip from Chicago. There are a couple good options. Take a trip to Milwaukee, Wisconsin for example. There are plenty of departure and return times out of Union Station starting in the early morning until late evening. The trip is just about an hour and a half between cities and it’s definitely worth your while. Traveling by train gets you easily from one downtown to another.
Looking for cheap train tickets to Chicago? 25% of our users found round-trip tickets to Chicago for the following prices or less: From Milwaukee $42, from Champaign $48, from South Bend $50
Chicago's most searched train station on KAYAK is Chicago Union. It is located 1 mile from the city center.
You will generally catch the best train deals if you travel to Chicago in the afternoon.
FAQs when traveling to Chicago by train
What is the most popular train station in Chicago?
Chicago Union is the most searched station in Chicago by KAYAK users.
Which train companies travel to Chicago?
Amtrak is the only train company serving Chicago.
How long is the train journey to Chicago from the closest popular cities?
Milwaukee to Chicago - 1h 19m
Springfield to Chicago - 3h 14m
East Lansing to Chicago - 3h 51m
Champaign to Chicago - 2h 37m
Bloomington to Chicago - 2h 24m
South Bend to Chicago - 1h 54m
St. Louis to Chicago - 4h 55m
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