Flights New York → Chicago — September 17, 2026

One way · Economy · 1 adult · price per person

The cheapest itinerary observed for Thursday, September 17, 2026 on the New York–Chicago route: 1 stop itinerary (2 flights) via Orlando International (MCO), from Newark Liberty (EWR) to Chicago O'Hare (ORD), first flight Frontier Airlines F91659, departs 5:55 AM, arrives 10:59 PM, total travel time 18h 4m including layovers, flight time 6h (layovers excluded), $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. Price found in an Aviasales search on September 7, 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 AA3221, from New York JFK (JFK) to Chicago O'Hare (ORD), departs 6:55 AM, arrives 8:48 AM, direct, 2h 53m, $152 per person. Fare as listed by Aviasales: carry-on bag included, checked bag not included, changes not allowed, non-refundable.