Flights from Pittsburgh to Chicago

Cheapest flights from Pittsburgh

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Jul 16 - Wed, Jul 23

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$248 Roundtrip, found 4 days ago

$248

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Wed, Jul 16 from Pittsburgh Intl. to O'Hare Intl., returning Wed, Jul 23, priced at $248 found 4 days ago

Sat, Jul 19 - Tue, Jul 22

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$250 Roundtrip, found 4 days ago

$250

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Jul 19 from Pittsburgh Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $250 found 4 days ago

Sat, Jul 19 - Tue, Jul 22

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$250 Roundtrip, found 4 days ago

$250

Roundtrip

found 4 days ago

Select United flight, departing Sat, Jul 19 from Pittsburgh Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $250 found 4 days ago

Wed, Jul 16 - Tue, Jul 22

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$255 Roundtrip, found 4 days ago

$255

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Jul 16 from Pittsburgh Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $255 found 4 days ago

Sat, Jul 19 - Tue, Jul 22

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$260 Roundtrip, found 4 days ago

$260

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Jul 19 from Pittsburgh Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $260 found 4 days ago

Mon, Jul 21 - Wed, Jul 23

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$268 Roundtrip, found 4 days ago

$268

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Mon, Jul 21 from Pittsburgh Intl. to O'Hare Intl., returning Wed, Jul 23, priced at $268 found 4 days ago

Sat, Jul 19 - Tue, Jul 22

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$270 Roundtrip, found 4 days ago

$270

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Jul 19 from Pittsburgh Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $270 found 4 days ago

Wed, Jul 16 - Thu, Jul 24

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$271 Roundtrip, found 4 days ago

$271

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Jul 16 from Pittsburgh Intl. to O'Hare Intl., returning Thu, Jul 24, priced at $271 found 4 days ago

Sat, Jul 19 - Tue, Jul 22

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$275 Roundtrip, found 4 days ago

$275

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Jul 19 from Pittsburgh Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $275 found 4 days ago

Tue, Jul 22 - Fri, Jul 25

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$278 Roundtrip, found 4 days ago

$278

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Tue, Jul 22 from Pittsburgh Intl. to O'Hare Intl., returning Fri, Jul 25, priced at $278 found 4 days ago

Sat, Jul 19 - Tue, Jul 22

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$280 Roundtrip, found 4 days ago

$280

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Jul 19 from Pittsburgh Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $280 found 4 days ago

Sat, Jul 19 - Tue, Jul 22

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$285 Roundtrip, found 4 days ago

$285

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Jul 19 from Pittsburgh Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $285 found 4 days ago

Sat, Jul 19 - Thu, Jul 24

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$286 Roundtrip, found 4 days ago

$286

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Jul 19 from Pittsburgh Intl. to O'Hare Intl., returning Thu, Jul 24, priced at $286 found 4 days ago

Wed, Jul 16 - Fri, Jul 25

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$287 Roundtrip, found 4 days ago

$287

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Wed, Jul 16 from Pittsburgh Intl. to O'Hare Intl., returning Fri, Jul 25, priced at $287 found 4 days ago

Sat, Jul 19 - Tue, Jul 22

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$290 Roundtrip, found 4 days ago

$290

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Jul 19 from Pittsburgh Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $290 found 4 days ago

Tue, Jul 22 - Thu, Jul 24

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$294 Roundtrip, found 4 days ago

$294

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Jul 22 from Pittsburgh Intl. to O'Hare Intl., returning Thu, Jul 24, priced at $294 found 4 days ago

Wed, Jul 16 - Sun, Jul 20

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$300 Roundtrip, found 4 days ago

$300

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Jul 16 from Pittsburgh Intl. to O'Hare Intl., returning Sun, Jul 20, priced at $300 found 4 days ago

Sat, Jul 19 - Mon, Jul 21

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$302 Roundtrip, found 4 days ago

$302

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Jul 19 from Pittsburgh Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $302 found 4 days ago

Mon, Jul 21 - Thu, Jul 24

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$302 Roundtrip, found 4 days ago

$302

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Mon, Jul 21 from Pittsburgh Intl. to O'Hare Intl., returning Thu, Jul 24, priced at $302 found 4 days ago

Thu, Jul 17 - Wed, Jul 23

PIT

Pittsburgh Intl.

ORD

O'Hare Intl.

$316 Roundtrip, found 4 days ago

$316

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Jul 17 from Pittsburgh Intl. to O'Hare Intl., returning Wed, Jul 23, priced at $316 found 4 days ago