Flights New York → Chicago — September 22, 2026

One way · Economy · 1 adult · price per person

The cheapest itinerary observed for Tuesday, September 22, 2026 on the New York–Chicago route: 1 stop itinerary (2 flights) via Atlanta Hartsfield-Jackson (ATL), from New York JFK (JFK) to Chicago Midway (MDW), first flight Frontier Airlines F94731, departs 1:00 PM, arrives 5:46 PM, total travel time 5h 46m including layovers, flight time 4h 40m (layovers excluded), $111 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 6, 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 WN2412, from New York LaGuardia (LGA) to Chicago Midway (MDW), departs 7:25 AM, arrives 8:45 AM, direct, 2h 20m, $139 per person. Fare as listed by Aviasales: carry-on bag not included (personal item only), checked bag not included, changes not allowed, non-refundable.