July is the cheapest month to fly this route, with average fares around $174 round trip.
Average round-trip fares by departure month, based on current availability.
| Month | Avg Price | Lowest | Relative Cost | |
|---|---|---|---|---|
| May 2026 | $211 | $148 | Peak | |
| June 2026 | $182 | $128 | ||
| July 2026 | $174 | $118 | Best | |
| August 2026 | $191 | $158 |
Departing on Saturday offers the lowest average fares at $166. Tuesday departures are the most expensive at $194, a difference of $28.
The best time to fly is July. Set up an alert and we'll notify you when prices drop.
Get Started Free →The cheapest month to fly from Philadelphia to Chicago is July, with average round-trip fares around $174. The lowest fare found in July is $118.
Saturday departures are the cheapest, averaging $166 round trip. The most expensive day is Tuesday at $194.
Based on current pricing trends, booking for July travel offers the best value. Avoid May if possible, as fares average $211 compared to $174 in the cheapest month. August is a solid middle-ground option at $191.
Flying in July instead of May can save you approximately $37 per round trip. The cheapest month averages $174 while the most expensive averages $211.
Airlines, flight times, price calendar, and more for Philadelphia to Chicago
View PHL → ORD Details