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Explore your options and book your Chicago (Midway) to Washington, D.C. (Reagan National) flight with Southwest today! The average flying time for a direct flight from Chicago, IL to Washington DC is 1 hour 53 minutes; Most direct flights leave around CST; Air New Zealand flight # is today's earliest flight from Chicago, IL to Washington DC ( CST, Airbus A/) Southwest Airlines flight # is today's latest flight from Chicago, IL to.
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