The Daily Show is in Chicago for night one of the DNC. 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. To kick off night one of the DNC, former Chicago resident Jordan Klepper and Illinois Governor JB Pritzker take a tour of the city they love. They talk history, food, sports, and culture. And of course they stop for a drink or three along the way. "There's a lesson in every tough story." Michigan Gov. Gretchen Whitmer joins fellow Michigander Michael Kosta during the Democratic National Convention in Chicago to discuss 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.