S$98 Cheap Flights from Pittsburgh to Chicago

View S$98 flight on Sat, 23 Aug, 2025Opens in a new window

Popular airlines from Pittsburgh Intl. Airport (PIT) to Chicago

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Cheap Flights from Pittsburgh to Chicago (PIT-CHI)

Prices were available within the past 7 days and start at S$98 for one-way flights and S$486 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 16 Jul - Tue, 22 Jul
PIT
Pittsburgh
ORD
Chicago
S$486 Return, found 5 days ago
S$486
Return
found 5 days ago
Select Delta flight, departing Wed, 16 Jul from Pittsburgh to Chicago, returning Tue, 22 Jul, priced at S$486 found 5 days ago
JetBlue Airways
Thu, 10 Jul - Wed, 23 Jul
PIT
Pittsburgh
ORD
Chicago
S$493 Return, found 5 days ago
S$493
Return
found 5 days ago
Select JetBlue Airways flight, departing Thu, 10 Jul from Pittsburgh to Chicago, returning Wed, 23 Jul, priced at S$493 found 5 days ago
JetBlue Airways
Sun, 13 Jul - Wed, 23 Jul
PIT
Pittsburgh
ORD
Chicago
S$495 Return, found 5 days ago
S$495
Return
found 5 days ago
Select JetBlue Airways flight, departing Sun, 13 Jul from Pittsburgh to Chicago, returning Wed, 23 Jul, priced at S$495 found 5 days ago
American Airlines
Sun, 13 Jul - Sun, 20 Jul
PIT
Pittsburgh
ORD
Chicago
S$524 Return, found 5 days ago
S$524
Return
found 5 days ago
Select American Airlines flight, departing Sun, 13 Jul from Pittsburgh to Chicago, returning Sun, 20 Jul, priced at S$524 found 5 days ago
Delta
Sun, 13 Jul - Sun, 20 Jul
PIT
Pittsburgh
ORD
Chicago
S$527 Return, found 5 days ago
S$527
Return
found 5 days ago
Select Delta flight, departing Sun, 13 Jul from Pittsburgh to Chicago, returning Sun, 20 Jul, priced at S$527 found 5 days ago
JetBlue Airways
Thu, 10 Jul - Sat, 19 Jul
PIT
Pittsburgh
ORD
Chicago
S$530 Return, found 5 days ago
S$530
Return
found 5 days ago
Select JetBlue Airways flight, departing Thu, 10 Jul from Pittsburgh to Chicago, returning Sat, 19 Jul, priced at S$530 found 5 days ago
JetBlue Airways
Sun, 13 Jul - Sat, 19 Jul
PIT
Pittsburgh
ORD
Chicago
S$533 Return, found 5 days ago
S$533
Return
found 5 days ago
Select JetBlue Airways flight, departing Sun, 13 Jul from Pittsburgh to Chicago, returning Sat, 19 Jul, priced at S$533 found 5 days ago
United
Sun, 13 Jul - Sun, 20 Jul
PIT
Pittsburgh
ORD
Chicago
S$537 Return, found 5 days ago
S$537
Return
found 5 days ago
Select United flight, departing Sun, 13 Jul from Pittsburgh to Chicago, returning Sun, 20 Jul, priced at S$537 found 5 days ago
American Airlines
Sun, 13 Jul - Sun, 20 Jul
PIT
Pittsburgh
ORD
Chicago
S$543 Return, found 5 days ago
S$543
Return
found 5 days ago
Select American Airlines flight, departing Sun, 13 Jul from Pittsburgh to Chicago, returning Sun, 20 Jul, priced at S$543 found 5 days ago
Delta
Sun, 13 Jul - Sun, 20 Jul
PIT
Pittsburgh
ORD
Chicago
S$548 Return, found 5 days ago
S$548
Return
found 5 days ago
Select Delta flight, departing Sun, 13 Jul from Pittsburgh to Chicago, returning Sun, 20 Jul, priced at S$548 found 5 days ago

Find the cheapest month to fly from Pittsburgh (PIT) to Chicago (CHI)

June is typically the cheapest month to fly

From S$98 - S$493 per traveller.

Graph displaying average flight prices per month

Pittsburgh to Chicago route information
Origin airport
Pittsburgh Intl.
Destination airport
O'Hare Intl.
Return price
S$486
Distance
656 km

Perfect flights from Pittsburgh to Chicago

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*Note: Prices may vary based on availability and are subject to change.

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Chicago Airports

Chicago

Pittsburgh to O'Hare Intl.
S$485.80
*Available to Expedia members.