The Daily Show is in Chicago for night one of the DNC and Michael Kosta covers what to expect this week, including vague nightly themes, unsubstantiated rumors of surprise celebrity appearances, and a recycled Biden platform. Plus, Grace Kuhlenschmidt reports on a giant inflatable IUD and Jordan Klepper stops by to teach Tim Walz a thing or two about pandering to local crowds. Klepper then takes a tour of the city with Illinois Governor JB Pritzker. They talk history, food, sports, and culture. And, of course, they stop for a drink or three along the way. Plus, Michigan Gov. Gretchen Whitmer discusses her bestselling book, “True Gretch: What I’ve Learned About Life, Leadership, and Everything in Between.” She shares how taking on Donald Trump earned her the nickname “Big Gretch,” bridging the gap between her constituents as governor, serving as a co-chair for the Harris-Walz presidential campaign and swing-state strategy.