Find Trains
Deals
When to book
Tips
FAQs

CHI

$27 Find train tickets to Chicago

This is the cheapest price found by a KAYAK user in the last 72 hours by searching for a train to Chicago departing on 12/9. 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.
1 adult
Thu 12/18
Thu 12/25

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.

Recent return train deals to Chicago

Wed, Dec 3 - Thu, Dec 4
Amtrak Logo
7:08 pm - 9:45 pmChampaign-
Chicago Union
2h 37mnonstop
Amtrak Logo
4:05 pm - 6:36 pmChicago Union-
Champaign
2h 31mnonstop
$30Amtrak
Find Deal
Thu, Dec 11 - Sun, Dec 14
Amtrak Logo
1:05 pm - 2:34 pmMilwaukee Intermodal-
Chicago Union
1h 29mnonstop
Amtrak Logo
8:05 pm - 9:34 pmChicago Union-
Milwaukee Intermodal
1h 29mnonstop
$48Amtrak
Find Deal
Thu, Dec 11 - Sun, Dec 14
Amtrak Logo
7:45 pm - 9:04 pmMilwaukee Airport-
Chicago Union
1h 19mnonstop
Amtrak Logo
8:05 pm - 9:18 pmChicago Union-
Milwaukee Airport
1h 13mnonstop
$48Amtrak
Find Deal
Tue, Dec 9 - Tue, Dec 16
Amtrak Logo
7:35 am - 11:45 amFlint-
Chicago Union
5h 10mnonstop
Amtrak Logo
4:00 pm - 10:03 pmChicago Union-
Flint
5h 03mnonstop
$62Amtrak
Find Deal
Tue, Dec 9 - Sat, Dec 13
Amtrak Logo
7:35 am - 11:45 amFlint-
Chicago Union
5h 10mnonstop
Amtrak Logo
4:00 pm - 10:03 pmChicago Union-
Flint
5h 03mnonstop
$65Amtrak
Find Deal
Thu, Dec 11 - Sat, Dec 13
Amtrak Logo
7:35 am - 11:45 amFlint-
Chicago Union
5h 10mnonstop
Amtrak Logo
4:00 pm - 10:03 pmChicago Union-
Flint
5h 03mnonstop
$68Amtrak
Find Deal
Thu, Dec 4 - Sat, Dec 6
Amtrak Logo
7:35 am - 11:45 amFlint-
Chicago Union
5h 10mnonstop
Amtrak Logo
4:00 pm - 10:03 pmChicago Union-
Flint
5h 03mnonstop
$75Amtrak
Find Deal
Thu, Dec 11 - Mon, Dec 15
Amtrak Logo
6:00 am - 9:08 amGrand Rapids-
Chicago Union
4h 08mnonstop
Amtrak Logo
6:30 pm - 11:34 pmChicago Union-
Grand Rapids
4h 04mnonstop
$75Amtrak
Find Deal
Sat, Nov 29 - Sun, Nov 30
Amtrak Logo
9:07 am - 10:12 amSouth Bend Amtrak Station-
Chicago Union
2h 05mnonstop
Amtrak Logo
9:30 pm - 11:59 pmChicago Union-
South Bend Amtrak Station
1h 29mnonstop
$76Amtrak
Find Deal
Fri, Nov 28 - Mon, Dec 15
Amtrak Logo
9:00 pm - 10:40 pmKalamazoo-
Chicago Union
2h 40mnonstop
Amtrak Logo
6:45 am - 10:12 amChicago Union-
Kalamazoo
2h 27mnonstop
$76Amtrak
Find Deal

Good to know

Cheapest day

Tuesday

Most expensive day

Thursday

Average price (round-trip)

$83

Average price (one-way)

$43
Train tickets to Chicago are on average 27% less expensive on Tuesdays
Train tickets to Chicago are on average 13% more expensive on Thursdays
(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 Champaign $30, from Milwaukee $47, from Kalamazoo $76
  • 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 and Train are popular train companies operating in Chicago.

  • How long is the train journey to Chicago from the closest popular cities?

    Milwaukee to Chicago - 1h 19m
    East Lansing to Chicago - 3h 51m
    Kalamazoo to Chicago - 2h 40m
    Champaign to Chicago - 2h 37m
    Bloomington to Chicago - 2h 19m
    Grand Rapids to Chicago - 4h 08m
    South Bend to Chicago - 1h 54m

More options for your train ride to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Flights to Chicago
Hotels in Chicago
Car rentals in Chicago
Vacation rentals in Chicago