Quick Summary:

  • Question: What makes Chicago a great starting point for day trips?
  • Answer: Chicago is nicely placed for a number of day trips, being connected to some beautiful locations by train.
  • Question: What are some options for day trips from Chicago?
  • Answer: If you're living in Chicago or visiting the city and looking to spend a day somewhere different, here are some of the best day trips you can take from Chicago by train.


  • Updated with new information since originally published.
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  • Our editors recommend these diverse local experiences.

1. From Chicago to Milwaukee ⭐⭐⭐⭐⭐

From Chicago to Milwaukee | You Can Take These Day Trips From Chicago By Train
© SeanPavonePhoto/stock.adobe.com

2. From Chicago to Oak Park ⭐⭐⭐⭐⭐

Category: Activities
From Chicago to Oak Park | You Can Take These Day Trips From Chicago By Train
© Brad Pict/stock.adobe.com

3. Day Trip to Michigan City from Chicago

Day Trip to Michigan City from Chicago | You Can Take These Day Trips From Chicago By Train
© CLIFTON/stock.adobe.com

4. Kalamazoo from Chicago

Kalamazoo from Chicago | You Can Take These Day Trips From Chicago By Train
© Michael/stock.adobe.com

5. Day Trip to Libertyville from Chicago

Day Trip to Libertyville from Chicago | You Can Take These Day Trips From Chicago By Train
© Anatolii/stock.adobe.com

Summary & FAQ From Chicago to Milwaukee From Chicago to Oak Park Day Trip to Michigan City from Chicago Kalamazoo from Chicago Day Trip to Libertyville from Chicago

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