● Deals from
● Sweeping every destination…
$91usually $166−45%18 Nov 2026 · 1-stop · score 82/100 · Exceptional
Live check · This route is not on today’s below-usual board, so we re-scanned it just now: the current cheapest upcoming fare sits about 45% below its usual level.
Why so cheap?
Researching this route’s pricing right now — checking season, sales, capacity and route news…
Fares by departure date
Today’s fare is cheaper than 98% of the 40 fares tracked for this route.
Questions people ask about this route
- What is the lowest price for a flight from New York to Chicago right now?
- The lowest price our scan found today (2026-10-13) is $91 one-way fare, departing 18 Nov 2026, 1-stop. Fares move constantly — the link below re-checks live availability on Aviasales.
- Is $91 a good price for a New York to Chicago flight (JFK→CHI)?
- Yes by the data: this route usually costs about $166 (midpoint of Google Flights' typical price range), so $91 is 45% below usual and cheaper than 98% of the 40 fares tracked for this route. FareFloor's deal score for it is 82/100 as of 2026-10-13.
- When is the cheapest time to fly from New York to Chicago in the coming months?
- Across the departure windows our 2026-10-13 scan compared, the lowest-priced departure found is 18 Nov 2026 at $91 one-way fare. Method: we sweep this origin's destinations several times a day via Google Flights data and keep the cheapest round-trip window per route — a cheaper window can appear any day, so treat this as today's answer, not a permanent one.
- Is there a direct flight from New York to Chicago at this price?
- The cheapest fare found today is 1-stop. A direct option, where one exists, may cost more — check the live fare link for alternatives.