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We will be taking a vacation to visit family in Grand Marais, MN this summer, and are planning to make one overnight stop in Chicago. We have 2 kids, ages 4 and 5, and are looking for some ideas of places to stop and break that are kid-friendly and not too far off course. Any ideas or suggestions would be great! :)
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Sorry, but trying to cover nearly 1300 miles in two days is not going to be "kid friendly" no matter how you slice it. The only way to accomplish the first day's 700 mile drive to Chicago is to get on the Turnpikes and stay on them for 12 hours straight with your only stops at the service plazas. The second day is only marginally better at 580 miles, but much of that is on two lane roads (US-53 and MN-61) so another 10-12 hours in the car. You can try to stop at handy places every few hours, but this is not going to be a fun drive unless you add at least another half day to the journey.
AZBuck
I have to agree with Buck, and in fact, in some ways its even a bit worse.
The second day's 600 mile drive is a killer. Its practically a full day drive to Duluth (although I will note that US-53 is now a 4 lane expressway all the way to Superior) and that alone with take you 8 hours. Duluth to Grand Marias is only another 150 miles, but it is along an incredibly scenic highway, that is also slow going. You could easily spend a full day making this drive (in fact, just a few weeks ago I was up there and leaving from Duluth, I barely made it halfway to Grand Marias in one day.) Even if you skip all of the amazing attractions along this route, like Split Rock Lighthouse and Gooseberry Falls, just to name a couple, its still a route that is going to take you more than 3, and likely closer to 4 hours.
I have to agree, adding a half day is the only way you'll even be able to think about making this a fun trip, and a full 3rd day would be highly recommended.