S$139 Cheap Flights from Pittsburgh to Chicago

View S$139 flight on Thu, 5 Mar, 2026Opens in a new window

Popular airlines from Pittsburgh 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$139 for one-way flights and S$272 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 5 Mar - Mon, 16 Mar
PIT
Pittsburgh
ORD
Chicago
S$272 Return, found 5 days ago
S$272
Return
found 5 days ago
Select Delta flight, departing Thu, 5 Mar from Pittsburgh to Chicago, returning Mon, 16 Mar, priced at S$272 found 5 days ago
United
Thu, 5 Mar - Mon, 16 Mar
PIT
Pittsburgh
ORD
Chicago
S$285 Return, found 5 days ago
S$285
Return
found 5 days ago
Select United flight, departing Thu, 5 Mar from Pittsburgh to Chicago, returning Mon, 16 Mar, priced at S$285 found 5 days ago
American Airlines
Thu, 5 Mar - Mon, 16 Mar
PIT
Pittsburgh
ORD
Chicago
S$298 Return, found 5 days ago
S$298
Return
found 5 days ago
Select American Airlines flight, departing Thu, 5 Mar from Pittsburgh to Chicago, returning Mon, 16 Mar, priced at S$298 found 5 days ago
Delta
Thu, 5 Mar - Mon, 16 Mar
PIT
Pittsburgh
ORD
Chicago
S$324 Return, found 5 days ago
S$324
Return
found 5 days ago
Select Delta flight, departing Thu, 5 Mar from Pittsburgh to Chicago, returning Mon, 16 Mar, priced at S$324 found 5 days ago
United
Thu, 5 Mar - Mon, 16 Mar
PIT
Pittsburgh
ORD
Chicago
S$337 Return, found 5 days ago
S$337
Return
found 5 days ago
Select United flight, departing Thu, 5 Mar from Pittsburgh to Chicago, returning Mon, 16 Mar, priced at S$337 found 5 days ago
Delta
Thu, 5 Mar - Mon, 16 Mar
PIT
Pittsburgh
ORD
Chicago
S$342 Return, found 5 days ago
S$342
Return
found 5 days ago
Select Delta flight, departing Thu, 5 Mar from Pittsburgh to Chicago, returning Mon, 16 Mar, priced at S$342 found 5 days ago
Delta
Thu, 5 Mar - Mon, 16 Mar
PIT
Pittsburgh
ORD
Chicago
S$346 Return, found 5 days ago
S$346
Return
found 5 days ago
Select Delta flight, departing Thu, 5 Mar from Pittsburgh to Chicago, returning Mon, 16 Mar, priced at S$346 found 5 days ago
United
Thu, 5 Mar - Mon, 16 Mar
PIT
Pittsburgh
ORD
Chicago
S$355 Return, found 5 days ago
S$355
Return
found 5 days ago
Select United flight, departing Thu, 5 Mar from Pittsburgh to Chicago, returning Mon, 16 Mar, priced at S$355 found 5 days ago
Delta
Fri, 6 Mar - Tue, 10 Mar
PIT
Pittsburgh
ORD
Chicago
S$357 Return, found 22 hours ago
S$357
Return
found 22 hours ago
Select Delta flight, departing Fri, 6 Mar from Pittsburgh to Chicago, returning Tue, 10 Mar, priced at S$357 found 22 hours ago
United
Thu, 5 Mar - Mon, 16 Mar
PIT
Pittsburgh
ORD
Chicago
S$359 Return, found 5 days ago
S$359
Return
found 5 days ago
Select United flight, departing Thu, 5 Mar from Pittsburgh to Chicago, returning Mon, 16 Mar, priced at S$359 found 5 days ago
Pittsburgh to Chicago route information
Origin airport
Pittsburgh Intl.
Destination airport
O'Hare Intl.
Return price
S$272
Distance
656 km

Perfect flights from Pittsburgh to Chicago

Your Journey from Pittsburgh to Chicago

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Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, American Airlines, United. Our selection of flights from Pittsburgh Intl. to CHI-All Airports caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

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Experience the Vibrant Chicago

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

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