Cheap Flights from Pittsburgh to Chicago
No deal from Pittsburgh to Chicago has cleared our price bar yet. What we have seen on the route is below.
Across 3 months of observations from Pittsburgh to Chicago, the lowest round-trip fare we recorded was $116, in August. The typical fare was $255. August was the cheapest month we saw and October the dearest.
The most recent price we saw on this route was $267 on Frontier and Southwest, seen Oct 14. It is an unverified observation and may have changed.
See every deal <a href="/from/pittsburgh">from Pittsburgh</a>, <a href="/to/chicago">to Chicago</a>, or the return direction <a href="/from/chicago/to/pittsburgh">Chicago to Pittsburgh</a>.
Latest price we saw: Pittsburgh to Chicago
The most recent round-trip fare our sweep found on this route. It is not verified and may have changed since the date shown.
| From | Price | Per mile | Travel dates | Airline | Seen | Check price |
|---|---|---|---|---|---|---|
| Pittsburgh (PIT) to Chicago (MDW) | $267 | 33.3¢ | Feb 22 – Mar 2 | Frontier and Southwest | Oct 14 | Check price |
Price history: Pittsburgh to Chicago
What we observed by month, from our signals database. Unverified observations, not bookable prices.
| Month | Low | Typical | Sightings |
|---|---|---|---|
| Oct 2026 | $228 | $300 | 95 |
| Sep 2026 | $226 | $275 | 131 |
| Aug 2026 | $116 | $191 | 109 |
Frequently asked questions
How many flight deals from Pittsburgh to Chicago are on Sparkflights right now?
There are 0 verified deals from Pittsburgh to Chicago on the board right now. The list refreshes hourly.
What is the lowest price ever seen from Pittsburgh to Chicago?
The lowest fare we've recorded from Pittsburgh to Chicago is $116, based on 335 price observations over 3 months.
How much does a flight from Pittsburgh to Chicago cost?
The typical round-trip fare we observed from Pittsburgh to Chicago is $255, against a recorded low of $116. These are observations, not quotes.
When is the cheapest month to fly Pittsburgh to Chicago?
August was the cheapest month we observed from Pittsburgh to Chicago and October the dearest, over 3 months of data.
What is the current price from Pittsburgh to Chicago?
The most recent fare our sweep saw from Pittsburgh to Chicago is $267, on Oct 14. It is an unverified observation rather than a verified deal, so check it before booking.