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.

Tue, Jul 1 - Tue, Jul 8

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$267 Roundtrip, found 19 hours ago

$267

Roundtrip

found 19 hours ago

Select Delta flight, departing Tue, Jul 1 from Pittsburgh Intl. to Midway Intl., returning Tue, Jul 8, priced at $267 found 19 hours ago

Mon, Jun 30 - Sat, Jul 5

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$281 Roundtrip, found 19 hours ago

$281

Roundtrip

found 19 hours ago

Select Frontier Airlines flight, departing Mon, Jun 30 from Pittsburgh Intl. to Midway Intl., returning Sat, Jul 5, priced at $281 found 19 hours ago

Tue, Jul 1 - Fri, Jul 4

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$285 Roundtrip, found 19 hours ago

$285

Roundtrip

found 19 hours ago

Select Delta flight, departing Tue, Jul 1 from Pittsburgh Intl. to Midway Intl., returning Fri, Jul 4, priced at $285 found 19 hours ago

Mon, Jun 30 - Sat, Jul 5

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$320 Roundtrip, found 19 hours ago

$320

Roundtrip

found 19 hours ago

Select Frontier Airlines flight, departing Mon, Jun 30 from Pittsburgh Intl. to Midway Intl., returning Sat, Jul 5, priced at $320 found 19 hours ago

Mon, Jun 30 - Tue, Jul 8

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$324 Roundtrip, found 19 hours ago

$324

Roundtrip

found 19 hours ago

Select Delta flight, departing Mon, Jun 30 from Pittsburgh Intl. to Midway Intl., returning Tue, Jul 8, priced at $324 found 19 hours ago

Tue, Jul 1 - Mon, Jul 7

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$333 Roundtrip, found 19 hours ago

$333

Roundtrip

found 19 hours ago

Select Delta flight, departing Tue, Jul 1 from Pittsburgh Intl. to Midway Intl., returning Mon, Jul 7, priced at $333 found 19 hours ago

Mon, Jun 30 - Fri, Jul 4

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$342 Roundtrip, found 19 hours ago

$342

Roundtrip

found 19 hours ago

Select Delta flight, departing Mon, Jun 30 from Pittsburgh Intl. to Midway Intl., returning Fri, Jul 4, priced at $342 found 19 hours ago

Sat, Jun 28 - Tue, Jul 8

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$347 Roundtrip, found 19 hours ago

$347

Roundtrip

found 19 hours ago

Select Delta flight, departing Sat, Jun 28 from Pittsburgh Intl. to Midway Intl., returning Tue, Jul 8, priced at $347 found 19 hours ago

Mon, Jun 30 - Sat, Jul 5

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$359 Roundtrip, found 19 hours ago

$359

Roundtrip

found 19 hours ago

Select Delta flight, departing Mon, Jun 30 from Pittsburgh Intl. to Midway Intl., returning Sat, Jul 5, priced at $359 found 19 hours ago

Sat, Jun 28 - Fri, Jul 4

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$365 Roundtrip, found 19 hours ago

$365

Roundtrip

found 19 hours ago

Select Delta flight, departing Sat, Jun 28 from Pittsburgh Intl. to Midway Intl., returning Fri, Jul 4, priced at $365 found 19 hours ago

Mon, Jun 30 - Sat, Jul 5

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$389 Roundtrip, found 19 hours ago

$389

Roundtrip

found 19 hours ago

Select Delta flight, departing Mon, Jun 30 from Pittsburgh Intl. to Midway Intl., returning Sat, Jul 5, priced at $389 found 19 hours ago

Wed, Jul 2 - Wed, Jul 2

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$399 Roundtrip, found 19 hours ago

$399

Roundtrip

found 19 hours ago

Select Delta flight, departing Wed, Jul 2 from Pittsburgh Intl. to Midway Intl., returning Wed, Jul 2, priced at $399 found 19 hours ago

Fri, Jun 27 - Sat, Jul 5

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$412 Roundtrip, found 19 hours ago

$412

Roundtrip

found 19 hours ago

Select Frontier Airlines flight, departing Fri, Jun 27 from Pittsburgh Intl. to Midway Intl., returning Sat, Jul 5, priced at $412 found 19 hours ago

Mon, Jun 30 - Sat, Jul 5

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$419 Roundtrip, found 19 hours ago

$419

Roundtrip

found 19 hours ago

Select Delta flight, departing Mon, Jun 30 from Pittsburgh Intl. to Midway Intl., returning Sat, Jul 5, priced at $419 found 19 hours ago

Mon, Jun 30 - Thu, Jul 3

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$422 Roundtrip, found 19 hours ago

$422

Roundtrip

found 19 hours ago

Select Delta flight, departing Mon, Jun 30 from Pittsburgh Intl. to Midway Intl., returning Thu, Jul 3, priced at $422 found 19 hours ago

Sat, Jun 28 - Thu, Jul 3

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$445 Roundtrip, found 19 hours ago

$445

Roundtrip

found 19 hours ago

Select Delta flight, departing Sat, Jun 28 from Pittsburgh Intl. to Midway Intl., returning Thu, Jul 3, priced at $445 found 19 hours ago

Mon, Jun 30 - Sat, Jul 5

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$449 Roundtrip, found 19 hours ago

$449

Roundtrip

found 19 hours ago

Select Delta flight, departing Mon, Jun 30 from Pittsburgh Intl. to Midway Intl., returning Sat, Jul 5, priced at $449 found 19 hours ago

Mon, Jun 30 - Sat, Jul 5

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$499 Roundtrip, found 19 hours ago

$499

Roundtrip

found 19 hours ago

Select Delta flight, departing Mon, Jun 30 from Pittsburgh Intl. to Midway Intl., returning Sat, Jul 5, priced at $499 found 19 hours ago

Mon, Jun 30 - Sat, Jul 5

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$510 Roundtrip, found 19 hours ago

$510

Roundtrip

found 19 hours ago

Select Delta flight, departing Mon, Jun 30 from Pittsburgh Intl. to Midway Intl., returning Sat, Jul 5, priced at $510 found 19 hours ago

Thu, Jul 3 - Thu, Jul 3

PIT

Pittsburgh Intl.

MDW

Midway Intl.

$539 Roundtrip, found 19 hours ago

$539

Roundtrip

found 19 hours ago

Select Delta flight, departing Thu, Jul 3 from Pittsburgh Intl. to Midway Intl., returning Thu, Jul 3, priced at $539 found 19 hours ago