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- After accidentally damaging a neighbor's property, a homeless man embarks on an unlikely journey to right the wrong.
- Series regular Kelly Kiorpes recalls a hilarious and very true story of life in the Windy City.
- With the one million dollar prize on the line, the final three teams race to Chicago where they must complete their final challenges within the windy city's most iconic landmarks, including a trip to Wrigley Field, the home of the World Champion Chicago Cubs.