Flights New York → Chicago — September 18, 2026

One way · Economy · 1 adult · price per person

The cheapest itinerary observed for Friday, September 18, 2026 on the New York–Chicago route: 1 stop itinerary (2 flights) via Denver International (DEN), from New York LaGuardia (LGA) to Chicago Midway (MDW), first flight Southwest Airlines WN4240, departs 9:05 PM, arrives 9:20 AM the next day, total travel time 13h 15m including layovers, flight time 6h 35m (layovers excluded), $162 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, $162 per person. Fare as listed by Aviasales: carry-on bag included, checked bag not included, changes not allowed, non-refundable.