Flights New York → Chicago — September 21, 2026

One way · Economy · 1 adult · price per person

The cheapest itinerary observed for Monday, September 21, 2026 on the New York–Chicago route: 1 stop itinerary (2 flights) via Atlanta Hartsfield-Jackson (ATL), from New York JFK (JFK) to Chicago O'Hare (ORD), first flight Frontier Airlines F94731, departs 1:00 PM, arrives 6:23 PM, total travel time 6h 23m including layovers, flight time 5h 5m (layovers excluded), $126 per person. Fare as listed by Aviasales: carry-on bag not included (personal item only), 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: Southwest Airlines WN2411, from New York LaGuardia (LGA) to Chicago Midway (MDW), departs 6:00 AM, arrives 7:15 AM, direct, 2h 15m, $143 per person. Fare as listed by Aviasales: carry-on bag not included (personal item only), checked bag not included, changes not allowed, non-refundable.