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We are planning for a trip around Lake Michigan [from a Friday noon to Monday night]. We will be starting from Northbrook, IL. We are a group of 4 and will be taking a Corolla. All 4 of us can drive. When I checked in google maps for the closest route to the lake, it came up to 930 miles [19 hours]. This seems a bit aggressive to me to cover in 3.5 days.

google maps screenshot

I did a google search for travel logs but no luck. Some people have done it in weeks taking a lot of breaks.

Has anyone done this stretch in 3 or 4 days? Will it be too tiring?

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Living in Chicago I'd saying 3-4 days is incredibly unlikely. The traffic going north to – William Aug 21 '12 at 23:54
up vote 5 down vote accepted

Tiring, maybe. But consider that there are four of you in a car for 3.5 days, during which you'll be stuck in that metal box for 5-7 hours a day. That's a LOT.

On the flipside, it is only for 3.5 days. I did a trip in South Africa where we drove 7300km (4500miles) in 22 days. It is possible. We took turns, each person being the driver for the day. We took regular breaks. Music, the like to keep us entertained. Good scenery. Animals in the game reserves.

So consider - you drive essentially a full work day each day driving. You're not going to have much time to see places, get out and explore.

Short answer: It's possible. But why not wait until you can spend a bit longer (even a couple of days more) and really enjoy it.

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