Cheap Flights from Pittsburgh to Chicago
Browse current best options from Pittsburgh. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Pittsburgh
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated today
456 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated Aug 31, 2026.)
Today’s best flight deals from Pittsburgh to Chicago
Explore current cheapest deals departing from Pittsburgh to Chicago
2026-09-21 – 2026-09-23
PIT - Chicago
76% AI deal score
$256
$135
Round trip
2026-10-12 – 2026-10-17
PIT - Chicago
48% AI deal score
$151
$135
Round trip
2026-10-13 – 2026-10-15
PIT - Chicago
49% AI deal score
$154
$135
Round trip
2026-10-03 – 2026-10-05
PIT - Chicago
48% AI deal score
$153
$135
Round trip
2026-10-20 – 2026-10-22
PIT - Chicago
48% AI deal score
$159
$135
Round trip
2026-10-22 – 2026-10-29
PIT - Chicago
47% AI deal score
$147
$135
Round trip
2026-11-07 – 2026-11-09
PIT - Chicago
49% AI deal score
$158
$135
Round trip
2027-02-18 – 2027-02-22
PIT - Chicago
49% AI deal score
$153
$135
Round trip
2026-09-23 – 2026-09-28
PIT - Chicago
75% AI deal score
$248
$136
Round trip
2026-10-17 – 2026-10-19
PIT - Chicago
48% AI deal score
$159
$136
Round trip
