Flights from Pittsfield to Chicago

Cheapest flights from Pittsfield

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.

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$621 Roundtrip, found 3 days ago

$621

Roundtrip

found 3 days ago

Select United flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $621 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$626 Roundtrip, found 3 days ago

$626

Roundtrip

found 3 days ago

Select United flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $626 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$631 Roundtrip, found 3 days ago

$631

Roundtrip

found 3 days ago

Select United flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $631 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$638 Roundtrip, found 3 days ago

$638

Roundtrip

found 3 days ago

Select United flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $638 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$641 Roundtrip, found 3 days ago

$641

Roundtrip

found 3 days ago

Select Delta flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $641 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$659 Roundtrip, found 3 days ago

$659

Roundtrip

found 3 days ago

Select United flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $659 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$669 Roundtrip, found 3 days ago

$669

Roundtrip

found 3 days ago

Select Delta flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $669 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$703 Roundtrip, found 3 days ago

$703

Roundtrip

found 3 days ago

Select United flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $703 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$709 Roundtrip, found 3 days ago

$709

Roundtrip

found 3 days ago

Select United flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $709 found 3 days ago

Tue, Jun 17 - Sun, Jun 22

ALB

Albany Intl.

ORD

O'Hare Intl.

$714 Roundtrip, found 1 day ago

$714

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Jun 17 from Albany Intl. to O'Hare Intl., returning Sun, Jun 22, priced at $714 found 1 day ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$728 Roundtrip, found 3 days ago

$728

Roundtrip

found 3 days ago

Select United flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $728 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$731 Roundtrip, found 3 days ago

$731

Roundtrip

found 3 days ago

Select United flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $731 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$745 Roundtrip, found 3 days ago

$745

Roundtrip

found 3 days ago

Select Delta flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $745 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$750 Roundtrip, found 3 days ago

$750

Roundtrip

found 3 days ago

Select Delta flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $750 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$752 Roundtrip, found 3 days ago

$752

Roundtrip

found 3 days ago

Select United flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $752 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$754 Roundtrip, found 3 days ago

$754

Roundtrip

found 3 days ago

Select Delta flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $754 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$760 Roundtrip, found 3 days ago

$760

Roundtrip

found 3 days ago

Select Delta flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $760 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$763 Roundtrip, found 3 days ago

$763

Roundtrip

found 3 days ago

Select United flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $763 found 3 days ago

Mon, Jun 23 - Mon, Jun 23

ALB

Albany Intl.

ORD

O'Hare Intl.

$781 Roundtrip, found 3 days ago

$781

Roundtrip

found 3 days ago

Select Delta flight, departing Mon, Jun 23 from Albany Intl. to O'Hare Intl., returning Mon, Jun 23, priced at $781 found 3 days ago

Thu, Jun 19 - Thu, Jun 19

ALB

Albany Intl.

ORD

O'Hare Intl.

$782 Roundtrip, found 1 day ago

$782

Roundtrip

found 1 day ago

Select United flight, departing Thu, Jun 19 from Albany Intl. to O'Hare Intl., returning Thu, Jun 19, priced at $782 found 1 day ago