Labor Day weekend is the perfect time to plan a quick Midwestern Road Trip. Luckily for us, our friends over at City Cast Madison aren’t too far away. So we asked host Bianca Martin to design her ideal Chicago day, while our host Jacoby Cochran comes up with his own Madison trip. And of course we wouldn’t be us if we didn’t make the two hosts compete for “Best Midwestern Daycation!”

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