Route Price Intelligence
Cheap Flights From Pittsburgh to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Chicago usually costs around $315 round trip from Pittsburgh, and today American has it at $137, more than half off. It's a nonstop hop that's perfect for a long weekend of deep dish, architecture tours, and lakefront walks this fall. Nonstop fares this low on this city pair are rare.
✓ 10 date combinations found at this price
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Best Time to Fly from Pittsburgh to Chicago
The cheapest time to fly from Pittsburgh to Chicago is typically May, when fares average around $284. The most expensive month tends to be April at around $446. For the best deals, consider flying in May, June, 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