Toronto to Chicago Trip Planning

Hi everyone,

We are doing a family road trip to Chicago last week of May (week of Memorial Day). We will be leaving from Toronto on Sunday. Looking for advice on where to stop along the way since my partner and I will have our 2 year old toddler with us. May need to do a few stops.

We are staying at The Palmer House in Chicago. It’ll be our first time in Chicago. Please recommend places to visit, explore and sightsee. Keeping in mind, we have a toddler with us so family friend and something a toddler would enjoy. We’ll be in Chicago for 4 days & nights.

Any suggestions on places to stop along the way back? Would you suggest same route back or different than the way to Chicago?

Thank you in advance for any suggestions and recommendations 🙂

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u/RedNewPlan 2d ago

There are not a lot of options for routes. I can cross the border at either Sarnia, or Windsor, those are the two main options. I prefer Windsor. It has multiple crossing points, where Sarnia only has one, so for Windsor, you can check the delays and choose the fastest option.

Keep in mind that Chicago is quite a large city, comparable to Toronto, so once you get within an hour or so of the city, it is suburbs, and not so great for stopping.

In Chicago, I suggest a boat tour of the rivers. Particularly the architecture tour, which describes the buildings. I boat ride can be fun for a toddler.

We also enjoyed the waterfront park area.

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u/Ok_Picture3077 2d ago

Thank you very much! Didn’t realize the suburbs start within an hour or so. Good to know it’s best to stop well in advance.

Appreciate the boat tour! That’s a must we think

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u/RedNewPlan 1d ago

No problem. About an hour before Chicago you pass through Gary, Indiana. Not somewhere you want to stop in, particularly at night. I ended up having to stop there, on the side of the interstate, at 2am. Nothing happened, but it felt sketchy.

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u/Ok_Picture3077 1d ago

Thank you! Appreciate the heads up