There are most likely no direct flights on the Pittsburgh — Chicago route
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A non-stop flight is the most convenient and comfortable way to fly from Pittsburgh to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
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Answers to questions about the route that travelers are most interested in.
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There are most likely no direct flights on the Pittsburgh — Chicago route
Pittsburgh — Chicago
09/04/2026
Departure
Direct flight
UA2180
starting at $366
Pittsburgh — Chicago
09/08/2026
Departure
Direct flight
AA1173
starting at $225
Pittsburgh — Chicago
09/09/2026
Departure
Direct flight
AA4525
starting at $365
Pittsburgh — Chicago
09/10/2026
Departure
Direct flight
WN2278
starting at $220
Pittsburgh — Chicago
09/13/2026
Departure
Direct flight
AA2675
starting at $355
Pittsburgh — Chicago
10/25/2026
Departure
Direct flight
WN4221
starting at $209
starting at $366
starting at $165
starting at $209
starting at $144
More than 4 airlines operate flights from Pittsburgh to Chicago, including United Airlines, American Airlines, Southwest Airlines, and Frontier Airlines. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $144, and our service lets you instantly compare all options. The variety of offers simplifies planning: you can choose budget fares or more comfortable options with baggage included or extra services. We help you find the best deals so your trip is cost-efficient.
The cheapest one-way flight from Pittsburgh to Chicago departs on 09/10/2026, is operated by Frontier Airlines and costs $144
The cheapest roundtrip flight from Pittsburgh to Chicago departs on 10/21/2026, is operated by Southwest Airlines and costs $287
Fastest flight from Pittsburgh to Chicago takes 1h 30m
There are direct flights on this route 5 days a week: Su, Tu, We, Th, and Fr
The distance between Pittsburgh and Chicago is 658km (408 miles). There are 102 direct flights from Pittsburgh to Chicago. The time difference between Pittsburgh and Chicago is 1h. Flights from Pittsburgh begin at 5:21 AM. The latest flight from Pittsburgh departs at 8:59 PM
The cheapest flight ticket from Pittsburgh to Chicago according to data for the last 48 hours costs $144
Often the best time to buy tickets from Pittsburgh to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Pittsburgh to Chicago can be found flying in these months: September, October.
The fastest flights from Pittsburgh to Chicago start from 1 hour 30 minutes in the air.
The following airlines operate direct flights on the route Pittsburgh — Chicago: United Airlines, American Airlines, Southwest Airlines
The cost of a one-way flight from Pittsburgh to Chicago ranges from $135 (September 2026) to $209 (October 2026). On average, the ticket price is about $172–$209.
We couldn't find any special offers for flights from Pittsburgh to Chicago