Rachael Ray sets out for America's heartland and finds herself in Milwaukee, WI, just itching to spend her $40 she's got burning in her wallet. It's breakfast at Katie's, a funky fifties-style diner, lunch at The Safehouse, and dinner at Three Brothers.

Rachael Ray toddles into the Windy City of Chicago with a farmer-sized appetite and just $40. She hits Kitsch 'n on Roscoe for breakfast, and Back Stage Bistro for lunch. For dinner she tries Greek Islands, a Greek family restaurant. The evening ends at Navy Pier with macadamia popcorn.