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.


Table of Contents


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.

Related:  Surprise Getaway from Toronto - Guess Where Trips | Ontario Review

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
Related:  (VIDEO) - Chicago Road Trip Captured Two Ways

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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Maria is the founder of SYDE Road, a blog about adventure and often-times dog-friendly traveling. She loves researching and planning for trips and is the 'project manager' for many of the small group adventures documented on this blog. She believes that while it is always best to go into a trip with a plan, the best planned trips are always the ones that have time built-in to explore and get a bit lost. Her itineraries are detailed with safety hints and tips, but are also peppered with unique travel stories and experiences that are the result of free time, getting lost, or stepping off the main trails. She aims to inspire others and give people the confidence to travel the world and get a bit sidetracked!

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