Flights New York → Chicago — September 14, 2026

One way · Economy · 1 adult · price per person

The cheapest itinerary observed for Monday, September 14, 2026 on the New York–Chicago route: 1 stop itinerary (2 flights) via Boston Logan (BOS), from New York JFK (JFK) to Chicago O'Hare (ORD), first flight American Airlines AA4397, departs 3:30 PM, arrives 8:05 PM, total travel time 5h 35m including layovers, flight time 4h 45m (layovers excluded), $155 per person. Fare as listed by Aviasales: carry-on bag included, checked bag not included, changes not allowed, non-refundable. Price found in an Aviasales search on September 8, 2026 and read by AirSource on September 10, 2026, 19:00 UTC: it is not guaranteed and is confirmed on Aviasales at booking time. The cheapest direct flight observed: American Airlines AA2841, from New York LaGuardia (LGA) to Chicago O'Hare (ORD), departs 9:29 PM, arrives 11:15 PM, direct, 2h 46m, $168 per person. Fare as listed by Aviasales: carry-on bag included, checked bag not included, changes not allowed, non-refundable.