Louis calls Matt from Chicago. Matt talks gives tip on taking the Greyhound Bus, and when to check out of a hotel. Louis talks about bringing warm weather clothes to a cold weather tour. Matt talks about his vacation to the Catskills, rental car tips in the trip-state area, commuting from the city to the suburbs, Zipcar, and his trip to MD, DC, and Atlantic City.

Matt and Louis discuss new cars versus old cars, hecklers, Tom Segura's Canadian tour, flying private, Matt's last trip to Calgary (2018), precheck at the airport, airline credit cards, the airport lounge, timing airport security, public confrontations, and the Catholic Church.