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WebFlights from Los Angeles to Chicago with American Airlines. Round trip. expand_more. 1 Adult, Economy class. expand_more. From. close. To. close. Depart 04/19/23. today. Return 04/26/23. today. Search. Home; American Airlines flights; Flights to United States; Los Angeles to Chicago; Recent searches for flights from Los Angeles to Chicago . From. WebThe cheapest flight from Los Angeles to Chicago O'Hare Airport was found 30 days before departure, on average. Book at least 2 weeks before departure in order to get a below-average price. High season is considered to be May, June and July. The cheapest month to fly is January. WebThe cheapest flight from Los Angeles to Chicago was found 63 days before departure, on average. Book at least 2 weeks before departure in order to get a below-average price. … symbol that speaks to you most