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.

Sat, Aug 30 - Mon, Sep 1

ALB

Albany Intl.

ORD

O'Hare Intl.

$231 Roundtrip, found 4 days ago

$231

Roundtrip

found 4 days ago

Select United flight, departing Sat, Aug 30 from Albany Intl. to O'Hare Intl., returning Mon, Sep 1, priced at $231 found 4 days ago

Wed, Aug 27 - Sat, Sep 6

ALB

Albany Intl.

ORD

O'Hare Intl.

$237 Roundtrip, found 4 days ago

$237

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Aug 27 from Albany Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $237 found 4 days ago

Sat, Aug 30 - Mon, Sep 1

ALB

Albany Intl.

ORD

O'Hare Intl.

$241 Roundtrip, found 4 days ago

$241

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Aug 30 from Albany Intl. to O'Hare Intl., returning Mon, Sep 1, priced at $241 found 4 days ago

Sat, Aug 30 - Mon, Sep 1

ALB

Albany Intl.

ORD

O'Hare Intl.

$250 Roundtrip, found 4 days ago

$250

Roundtrip

found 4 days ago

Select United flight, departing Sat, Aug 30 from Albany Intl. to O'Hare Intl., returning Mon, Sep 1, priced at $250 found 4 days ago

Sat, Aug 30 - Mon, Sep 1

ALB

Albany Intl.

ORD

O'Hare Intl.

$252 Roundtrip, found 4 days ago

$252

Roundtrip

found 4 days ago

Select United flight, departing Sat, Aug 30 from Albany Intl. to O'Hare Intl., returning Mon, Sep 1, priced at $252 found 4 days ago

Sat, Aug 30 - Mon, Sep 1

ALB

Albany Intl.

ORD

O'Hare Intl.

$257 Roundtrip, found 4 days ago

$257

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Aug 30 from Albany Intl. to O'Hare Intl., returning Mon, Sep 1, priced at $257 found 4 days ago

Sat, Aug 30 - Mon, Sep 1

ALB

Albany Intl.

ORD

O'Hare Intl.

$266 Roundtrip, found 4 days ago

$266

Roundtrip

found 4 days ago

Select United flight, departing Sat, Aug 30 from Albany Intl. to O'Hare Intl., returning Mon, Sep 1, priced at $266 found 4 days ago

Sat, Aug 30 - Mon, Sep 1

ALB

Albany Intl.

ORD

O'Hare Intl.

$266 Roundtrip, found 4 days ago

$266

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Aug 30 from Albany Intl. to O'Hare Intl., returning Mon, Sep 1, priced at $266 found 4 days ago

Fri, Aug 29 - Mon, Sep 8

ALB

Albany Intl.

ORD

O'Hare Intl.

$266 Roundtrip, found 6 days ago

$266

Roundtrip

found 6 days ago

Select American Airlines flight, departing Fri, Aug 29 from Albany Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $266 found 6 days ago

Fri, Aug 29 - Mon, Sep 8

ALB

Albany Intl.

ORD

O'Hare Intl.

$268 Roundtrip, found 6 days ago

$268

Roundtrip

found 6 days ago

Select United flight, departing Fri, Aug 29 from Albany Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $268 found 6 days ago

Sun, Aug 31 - Tue, Sep 2

ALB

Albany Intl.

ORD

O'Hare Intl.

$269 Roundtrip, found 4 days ago

$269

Roundtrip

found 4 days ago

Select Delta flight, departing Sun, Aug 31 from Albany Intl. to O'Hare Intl., returning Tue, Sep 2, priced at $269 found 4 days ago

Sat, Aug 30 - Mon, Sep 1

ALB

Albany Intl.

ORD

O'Hare Intl.

$276 Roundtrip, found 4 days ago

$276

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Aug 30 from Albany Intl. to O'Hare Intl., returning Mon, Sep 1, priced at $276 found 4 days ago

Fri, Aug 29 - Mon, Sep 8

ALB

Albany Intl.

ORD

O'Hare Intl.

$277 Roundtrip, found 6 days ago

$277

Roundtrip

found 6 days ago

Select United flight, departing Fri, Aug 29 from Albany Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $277 found 6 days ago

Sat, Aug 30 - Mon, Sep 1

ALB

Albany Intl.

ORD

O'Hare Intl.

$278 Roundtrip, found 4 days ago

$278

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Aug 30 from Albany Intl. to O'Hare Intl., returning Mon, Sep 1, priced at $278 found 4 days ago

Fri, Aug 29 - Mon, Sep 8

ALB

Albany Intl.

ORD

O'Hare Intl.

$281 Roundtrip, found 6 days ago

$281

Roundtrip

found 6 days ago

Select American Airlines flight, departing Fri, Aug 29 from Albany Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $281 found 6 days ago

Sat, Aug 30 - Mon, Sep 1

ALB

Albany Intl.

ORD

O'Hare Intl.

$282 Roundtrip, found 4 days ago

$282

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Aug 30 from Albany Intl. to O'Hare Intl., returning Mon, Sep 1, priced at $282 found 4 days ago

Sat, Aug 30 - Mon, Sep 1

ALB

Albany Intl.

ORD

O'Hare Intl.

$284 Roundtrip, found 4 days ago

$284

Roundtrip

found 4 days ago

Select United flight, departing Sat, Aug 30 from Albany Intl. to O'Hare Intl., returning Mon, Sep 1, priced at $284 found 4 days ago

Fri, Aug 29 - Mon, Sep 8

ALB

Albany Intl.

ORD

O'Hare Intl.

$286 Roundtrip, found 6 days ago

$286

Roundtrip

found 6 days ago

Select American Airlines flight, departing Fri, Aug 29 from Albany Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $286 found 6 days ago

Sat, Aug 30 - Mon, Sep 1

ALB

Albany Intl.

ORD

O'Hare Intl.

$287 Roundtrip, found 4 days ago

$287

Roundtrip

found 4 days ago

Select United flight, departing Sat, Aug 30 from Albany Intl. to O'Hare Intl., returning Mon, Sep 1, priced at $287 found 4 days ago

Sat, Aug 30 - Mon, Sep 1

ALB

Albany Intl.

ORD

O'Hare Intl.

$287 Roundtrip, found 4 days ago

$287

Roundtrip

found 4 days ago

Select United flight, departing Sat, Aug 30 from Albany Intl. to O'Hare Intl., returning Mon, Sep 1, priced at $287 found 4 days ago