Route Price Intelligence
Cheap Flights From Pittsburgh to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Chicago from Pittsburgh is running $137 round trip, down from a typical $314, a 56% discount and one of the steepest drops we are tracking this week. Deep dish pizza, the Riverwalk, and Lake Michigan's summer waterfront are all just over an hour away. It's a great value fare for a quick city break this season.
✓ 15 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