Night two of the tour is a big one for Kristin as she gears up for the Windy City and a high school reunion like no other with her friends from Laguna Beach; the old classmates catch up and spill some 20+ year secrets.

On her day off in Chicago, Kristin checks in on her Uncommon James store followed by a dinner with friends that takes a turn; her entourage heads to Boston where Camille Kostek joins her on stage.