A first-class letter mailed through the U.S. Postal Service takes, on average, three days to go from Tennessee to Chicago, according to the USPS map server. The Postal Service does...Jul 23, 2020 · Stretching from Chicago to the Santa Monica Pier, the legendary Route 66 road trip is arguably one of the most famous in the world, crossing eight states and three time zones. The trip will take you past some of the country’s most iconic roadside scenes, from neon signage and middle-of-nowhere truck stops to kitschy Americana.

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There are several routes you can take between Chicago and San Francisco. But since we only had around five days to make the trip, we took the most direct: the I-80 road trip. Yes, that’s one road for 30+ hours. When you get on the highway, your GPS will say: “continue on I-80 for 2,000-something miles.”. Pretty insane!

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