Road Trip to Chicago Day ONE – Commute, Deep Dish Pizza, and Turtle Racing

Road Trip to Chicago Day ONE – Commute, Deep Dish Pizza, and Turtle Racing

This post is an additional post to the Road Trip to Chicago From Toronto – Four Day Itinerary. Day Two details can be found here.

Day One focuses on the drive from Toronto to Chicago, our first Deep Dish pizza experience, and Turtle Racing.



4 Day Road Trip Itinerary – Toronto to Chicago and Back

As a reminder, here is our 4-day itinerary:

Our Experience with Day One

  • 6:00 AM – Leave Toronto
  • 9:30 AM – Stop in Windsor to eat at A Dog’s Breakfast
  • 12:00 PM – Find the Detroit-Windsor Tunnel and cross the border.
  • 5:30 PM – Arrive in Chicago!
    • We checked in at the Ohio House Motel and ordered delivery from Lou Malnati’s
  • 8:30pm – Take an Uber to Big Joe’s to watch some Turtle Racing (note: Turtle Racing only happens on Fridays so plan accordingly!)
  • 12:30am – That’s a wrap for day one in Chicago

****Maria’s Tip – Weekday Vacation Start? Leave at 6:00 AM from Toronto to Avoid Rush Hour in Toronto, Windsor, Detroit, and Chicago! SUPER WIN****

Our first day of the trip began on a Friday. My friend recommended that we start at 6:00AM to avoid conflicts with rush hour traffic times.

By leaving at 6:00 AM, you are able to leave before most of the working commuters heading into Toronto make their way onto the highways. From personal experience, the Toronto morning commuter rush starts at 7:00 AM and doesn’t end until well past 9:30 AM.

By 9:30 AM, we had arrived in Windsor, where it was recommended we take a quick breakfast break to avoid the tail-end of the cross-border morning commute. Similar to the Toronto morning commute, the cross-border traffic peaks from 7:00 AM and lasts until 10:00 AM.

Then as an added bonus, the distance from Detroit to Chicago is about 4.5 hours, and even if you take a couple of bathroom pit stops, you should arrive into the core of Chicago no later than 4:30 PM – before the congestion from the evening commuter rush really picks up – leaving you with enough time to relax for the evening with still enough time to explore parts of the city before calling it a night. Because we got lost and lost time, we ended up arriving in Chicago at 5:30 PM instead – hitting congestion head-on.

****Maria’s Tip – If you aren’t comfortable driving long distances but want to expand your experience, offer to drive more familiar roads first – like…. driving on the Canadian side instead of the American side****

I’m really excited to write this as it’s something I’m pretty proud of – I doubled my 2-hour driving threshold! I can now drive for FOUR HOURS without quitting. As someone who doesn’t drive much beyond the weekend trips to the grocery store, this is a monumental step for me. Sure, my butt was sore, but I did it.

  • 24 hours before our trip, our AirBnB host cancelled on us, so Ohio House Motel wasn’t actually our first pick but it worked out
  • We got lost trying to find the Detroit-Windsor tunnel, and our conversation with the border control officer was longer than usual
  • We loved the Turtle Racing experience so much! Our favorite experience in Chicago by far – check out the video below so that you can enjoy the excitement with us

Turtle Racing at Big Joe’s (video)

And that concludes our first day of the four-day road trip to Chicago! You can head back to the general itinerary guide again by clicking here, or head on over to Road Trip to Chicago Day TWO – Around Millennium Park for a more detailed account and experience of the next day.

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