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Arriving at the South Gate, Hayden & Aaron stepped onto the mat in third place. However, due to their penalty, they fell to last place and became the eighth and final Team eliminated from THE AMAZING RACE. Disappointed in her performance, Hayden received the surprise of a lifetime when Aaron dropped to one knee and offered his hand in marriage. The shocked Hayden accepted his proposal through her tears as Aaron joked, "She's speechless for once." The emotion of the moment also affected Aaron as he choked up, telling Hayden, "I love you so much."
AMERICA AWAITS
Departing the Pit Stop in first place at 5:27 am, Kris & Jon opened their clue to learn they had to fly over 5,600 miles to Honolulu, Hawaii. Once there, they must drive to Puu Ualakaa State Park and find the next Route Marker at a lookout point. By going to a hotel instead of a travel agency, Freddy & Kendra pulled into the lead by booking a flight landing in Honolulu at 9:30 am, while Kris & Jon settled for a flight arriving at 9:45 am. Being several hours behind, Adam & Rebecca booked seats on a flight landing in Hawaii at 11 am. However, the formerly dating couple almost caught up in Osaka, Japan, but when trying to get on Freddy & Kendra's connecting flight, Adam & Rebecca were turned away as the plane had already boarded, sending Adam into a rage.
Touching down in Hawaii in first place, Freddy & Kendra drove on the interstate to Puu Ualakaa State Park with Kris & Jon 15 minutes behind. Arriving at the lookout point, Freddy & Kendra opened their clue to discover a Detour. In this Detour, Teams had to choose between Outfits and Outrigger. Outfits required Teams to travel 10 miles to a tropical clothing distributor and search racks filled with 165,000 articles of clothing for ones matching the outfit on a mannequin. After donning the outfits themselves, they would earn their next clue. For Outrigger, Teams had to drive six miles to a canoe club and, with the help of a steering person, paddle an outrigger canoe down a course over two miles long.
While Freddy & Kendra got lost on the way to the canoe club, Kris & Jon arrived at the clothing company. As Freddy & Kendra finally began paddling down the course, Kris & Jon found the matching clothes to complete the Detour. Opening their clue, they discovered they had to drive five miles to Kamaka Air for the next Route Marker.
WINDY CITY SHOWDOWN
As Adam & Rebecca opted for Outrigger, Kris & Jon arrived at the airport, followed closely by Freddy & Kendra. Opening their clue, the Teams found a Roadblock. In this Roadblock, one Team member must skydive 11,000 feet in tandem with an instructor, landing on a sandbar where their next clue waited. After taking the exhilarating plunge for his Team, Jon landed in the Pacific Ocean while Kris cheered nearby. Opening their next clue, the pair learned they were heading back to where it all began, Chicago, Illinois. Once there, they had to travel by train to the Water Tower, one of the few buildings to survive the Great Chicago Fire of 1871.
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