Season 4, Episode 6

A Food Truck Kind of Town, Chicago is

In Chicago, Tyler starts the finalists off on their 800-mile final trek with a Chicago-style pizza challenge judged by Mayor Rahm Emanuel. After the mayor chooses the winner, the teams get ready to sell all day in Chicago when they're given their speed bump: every time Tyler calls, they'll have to move a mile away from their current location. On day two, the teams must use another famed Chicago food in all their dishes - hot dogs. Once the teams make $500, they race to Mike Ditka's restaurant, where the first team to arrive will get a five hour head start to the next city, while the slackers are on dish washing duty.
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So Much Pretty Food Here