Trying to take a well-deserved break from their jobs, Ken and Sarah planned a weekend getaway to Chicago to visit friends, John and Charlotte, and discover new places. Chicago has always held a special place in Ken and Sarah's heart, as it was their very first trip together. Little did Sarah know that Ken had been plotting with John for weeks about much more than tourist activities. After their 6 hour drive, they stopped in downtown to eat at their favorite Chicago pizza place, Gino's. They enjoyed their deep dish pizza, walked around to avoid a food coma, and then continued driving just north of the city to John and Charlotte's house. They spent the next day and a half playing with John and Charlotte's children, Jackson and Claire, working out at the Naval base John was stationed at, and visiting Milwaukee. While in Milwaukee, they went to a Bucks game in their new arena and got to see Dwayne Wade play his last game in the city where he went to college. Sarah probably thought this was the most entertaining thing they would do during their trip, but she would be wrong. The next day, Ken told Sarah that John and his family were coming with them to tour the city and John wanted to try his new camera out. From the moment Ken picked to propose in Chicago, he knew Navy Pier was the place he wanted to do it at. As they were walking to and around Navy Pier, they all noticed the place was packed with people dancing and covered in powdered paint. Ken started to freak out and wonder if he would be able to find a location not engulfed in madness, with a view of the skyline. As they kept walking they found a portion of the pier that extended out over the water and was clear of people. Ken told John this was a great place for a picture and Sarah walked over to join him. After handing her phone to Charlotte to also take a picture, Sarah turned around to Ken on one knee, asking Sarah to be his wife. Neither of them remember what Ken said, but they both remember Sarah saying yes!