Cheap flights from Pittsburgh to Chicago
from 123 US$
From 251 USD — compare hundreds of airlines
The cheapest month is usually 2026-09 · 123 US$
See prices for my dates →Live fares from 100+ sites — free, with no hidden fees.
About this route
Compare flights from Pittsburgh to Chicago, a about 659 km route (around 1h 19m nonstop). We gather live prices from hundreds of airlines and agencies so you can find the cheapest and book on the official site, with no hidden fees. Direct flights are available. Airlines such as American Airlines, United Airlines, Southwest Airlines operate this route.
When to buy and when to fly
Prices by date
Fares found by date — cheapest days in green.
How to get the best price
Airlines on this route
FAQ
What's the cheapest month to fly Pittsburgh to Chicago?
It's usually 2026-09, from 123 USD. Use the price calendar to compare other dates.
How long is the flight from Pittsburgh to Chicago?
A nonstop flight takes about 1h 19m and covers around 659 km. Connecting itineraries take longer.
Are there direct flights from Pittsburgh to Chicago?
Yes, this route has nonstop flights. Filter by "nonstop" to see them.
Which airlines fly from Pittsburgh to Chicago?
American Airlines, United Airlines, Southwest Airlines operate this route, among others. Compare them all in the results.
When should I book Pittsburgh–Chicago flights?
As a rule of thumb, booking 3–8 weeks ahead and avoiding weekends and holidays tends to give the best prices. Use the calendar to spot the cheapest dates.
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Pittsburgh → Chicago · Live fares from 100+ sites — free, with no hidden fees.