August is the cheapest month to fly this route, with average fares around $178 round trip.
Average round-trip fares by departure month, based on current availability.
| Month | Avg Price | Lowest | Relative Cost | |
|---|---|---|---|---|
| May 2026 | $202 | $187 | Peak | |
| June 2026 | $186 | $177 | ||
| July 2026 | $182 | $177 | ||
| August 2026 | $178 | $177 | Best |
Departing on Tuesday offers the lowest average fares at $181. Friday departures are the most expensive at $191, a difference of $10.
The best time to fly is August. Set up an alert and we'll notify you when prices drop.
Get Started Free →The cheapest month to fly from New York to Chicago is August, with average round-trip fares around $178. The lowest fare found in August is $177.
Tuesday departures are the cheapest, averaging $181 round trip. The most expensive day is Friday at $191.
Based on current pricing trends, booking for August travel offers the best value. Avoid May if possible, as fares average $202 compared to $178 in the cheapest month. June is a solid middle-ground option at $186.
Flying in August instead of May can save you approximately $24 per round trip. The cheapest month averages $178 while the most expensive averages $202.
Airlines, flight times, price calendar, and more for New York to Chicago
View JFK → ORD Details