Fantasy Road Trip: Seattle to Chicago

Seattle to Chicago daydream route.

Update: Not just a fantasy anymore, we’re actually doing it.

Another update: We did it.

Sometimes the slightest thought can inspire an epic road trip. Innocent seeming quotes like “I’m visiting my sister in South Carolina this summer, want to come with?” or “I bet Maine is nice” have taken us on thousand-mile plus journeys. Our recent Southwestern road trip was roughly outlined between appetizer and entree at The Bento Box. Clearly it doesn’t take much to get us dreaming up a new adventure. So when I heard “If you want to go to Glacier National Park, we’re in,” I immediately went to Google Maps to see what that would involve. I guess it’s kind of an addiction, but everyone needs hobbies.

The attached map shows a bit of what goes into our first stage of planning. Select a destination, see how much time you have, and then trace a line that has varied points of interest and preferably takes you to places you’ve never been. This sample route would nicely fill in a blank spot in our map as we’ve never taken a path this far north and neither of us has been to Montana or North Dakota. It would involve a one-way flight to Seattle and then returning to Chicago via rental car. Since National Parks are a favorite of ours, we’ve included five. I also threw in a stop at Lake Itasca, Minnesota, because I couldn’t pass within a hundred miles of the source of the Mississippi River without making a detour. At more than 2,800 miles, this one would blow away our current road trip distance record and require at least a week and a half (more likely two weeks) to maintain an enjoyable pace. Alas, for now it’s just a thought as we have plenty of these fantasy maps up our sleeves.

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7 Responses to Fantasy Road Trip: Seattle to Chicago

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  4. Linda Bonnington says:

    Really interested in your trip as my son and I are planning to do the Seattle to Chicago drive in September this year. We shall be flying from the UK to Seattle and then back to the UK from Chicago. Looking for interesting places along the way. sadly we only have two weeks for the trip but hope to cover some of the less interesting areas quickly.

    • Neil says:

      Sounds great! Depending on what route you’re taking, we highly recommend hitting the western South Dakota/Black Hills region. There are lots of National Parks and Monuments in a compact area. We passed through that area on a previous trip so we’re heading across North Dakota this time. Two weeks should be a good amount of time to explore. Stay tuned, we’ll try to keep everyone updated with our findings while on the road.

      • Linda Bonnington says:

        We have booked our flights. We are having a couple of days in Chicago before flying to Seatlle, but the rest of the trip has not been planned yet. I am leaving the route to my son and I will then sort out the logistics! I did a tour a few years ago that covered South Dakota, included a quick trip to Yellowstone, and many other tourist attractions in the area. I don’t know if my son is planning the ND or SD route. Flights were booked last week, so this week’s priority is to decide how long we should take to get from Seattle to Yellowstone and book some accommodation while there is still some available.
        Enjoy your trip. I will watch this space with eager anticipation. Hoping to pick up some great tips and ideas of where to go along the way, route permitting!

  5. Pingback: Seattle to Chicago: Planning Timeline | highkicktravel

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