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I do my own F1 style loop through the city on early weekend mornings before 8 AM that’s pretty fun. 290 to lower wacker to LSD heading north, l loop back to wacker south, to 290 to Ashland, south to hit a couple long over passes (tunnels!), then back to 90 north, take the down town exits option, the new interchange is fun, and then i decide from there what to do, often off to grab breakfast.
It’s tough being a car lover in the city. If you have more time then you can head out to Ottawa (1.25 hrs) and then drive the river road down to Preoria and then loop back. It’s pretty fun but more like a half day.
I don’t drive too much of Sheridan as it’s slow moving and has cops camped out. DM me if you ever want to run the loop. I am still tweaking the route a bit for fun and new spots I am finding in the city.
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