by Robin B 

This guide has been updated July 1, 2017

Driving to Chicago can be a nightmare can’t it? You have to time your departure just right to avoid rush-hour traffic, and even then there is no guarantee you won’t be sitting in construction traffic pulling your hair out listening to the kids ask for the millionth and one time “when will we get there??”

There are a couple different options to consider for traveling to Chicago via the rails:


The Amtrak departs right from Kalamazoo and the entire trip takes around 2 ½ hours, with four stops total. Amtrak offers several departures daily.

RELATED: 10 Kid-Friendly Activities To Do With Kids In Chicago

(Photo courtesy of Michigan Department of Transportation (MDOT) Photo Unit)

Here are some tips we learned traveling via AMTRAK to Chicago:

  • The station in Kalamazoo isn’t very crowded (we departed on a weekday afternoon). The website suggests to arrive 30 minutes prior to departure and that is plenty of time.
  • It is simple to book tickets online – print out your ticket and have it ready to scan as you board the train.
  • The train lines offer general seating and there were plenty of open seats. Since it is a short distance, only carry-on items are allowed. However, AMTRAK carry-on item policy is quite generous.
  • Food is allowed on the train and we packed our own lunch. It must be eaten in your seats (not in the lounge car).
  • Kids love the diversion of walking between cars so plan on visiting the lounge car. Carry-on luggage must stay in your seat area/overhead bin, so take any valuables with you in a smaller bag/purse if you plan to visit the lounge car.
  • Before the first stop in Niles, the train picks up speed and can be bumpy. Once you round the bend into Illinois, the train is much slower and not nearly as bumpy.
  • This line is a pet-friendly route. For $25, dogs and cats (up to 20 pounds) are welcome to ride. Visit HERE for specific guideline information and how to make pet travel arrangements.
  • Wi-Fi available on the train, make sure to check out the Amtrak Kids Depot – a fun online resource for kids which includes games, activities and downloadable sheets.





The South Shore Line is a commuter rail line operated by the Northern Indiana Commuter Transportation District (NICTD).

Split the trip by driving to Indiana and you can hop aboard the South Shore Line on the commuter train to Chicago.There are several stations to choose from (such as Michigan City at 11th Street or at Carroll Ave. or Dune Park Station in Chesterton, IN), with a one-way fare costing just under $10 for an adult. The trip to Chicago’s Loop takes about an hour and a half.

The South Shore Line offers more daily options for train departure times, but try to avoid the rush hour times since it is a commuter train. Parking is free at most stations. The 11th Street station can fill quickly on the weekdays.

There are a number of options available to purchase train tickets – online, from a ticket agent, or from the ticket vending machine located at the stations. One-way and reduced one-way tickets are valid for 90 days from the date of sale, allowing for flexibility with travel dates.

Photo courtesy South Shore Line / NICTD

Tips for taking the South Shore Line:

  • Children under two years of age ride free in the arms or lap of an adult passenger.
  • Children under age 14 qualify for the Reduced One-way Fare, costing just under $5.00
  • Storage space is limited and luggage must be placed in overhead racks or under a seat.
  • Strollers are permitted on the train. However, since space can be tight, it is best to use umbrella-style or collapsable stroller if at all possible.
  • There are several stops to get off once in Chicago. Millennium Station, at Randolph St. and is near Millennium Park, Navy Pier, the Loop and and North Michigan Avenue shopping.

Photo courtesy Drew Jacksich

The South Shore Line is an inexpensive way to take a family day trip to Chicago with their Kids Ride Free program. On weekends, holiday and daily off-peak trains, 3 children under 14 years of age may ride free when accompanied by a parent or guardian.


Do you have any tips for taking the train into Chicago? If so, let us know!


Chicago Train-2




By | 2017-07-17T06:03:56+00:00 July 17th, 2017|Categories: Around Kalamazoo, Newly Published, Parent resources|Comments Off on All Aboard! Destination: The Windy City

About the Author:

Robin is a native Michigander and mother of two. She has a keen eye for discovering deals and an honest desire to share local activities and family fun. In addition to enjoying early mornings with strong coffee, she likes hanging outside with her kids, biking and reading.