Route Price Intelligence
Cheap Flights From Philadelphia to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
PHL to Chicago fares fell to $140 round trip, more than half off the usual price and comfortably above the $61 floor we have seen on this route, so it is a real discount rather than a one-off fluke. Chicago's deep dish, architecture river cruises, and lakefront make it an easy weekend add at this price.
✓ 4 date combinations found at this price
Search Google FlightsMonthly Price Guide
Best Time to Fly from Philadelphia to Chicago
The cheapest time to fly from Philadelphia to Chicago is typically September, when fares average around $190. The most expensive month tends to be July at around $339. For the best deals, consider flying in September, October, August.
Typical Price by Travel Month
Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route