Flights from Chicago to Windsor Locks

Cheapest flights from Chicago

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.

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$391 Roundtrip, found 1 day ago

$391

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $391 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$401 Roundtrip, found 1 day ago

$401

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $401 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$410 Roundtrip, found 1 day ago

$410

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $410 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$411 Roundtrip, found 1 day ago

$411

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $411 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$468 Roundtrip, found 1 day ago

$468

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $468 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$478 Roundtrip, found 1 day ago

$478

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $478 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$499 Roundtrip, found 1 day ago

$499

Roundtrip

found 1 day ago

Select United flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $499 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$516 Roundtrip, found 1 day ago

$516

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $516 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$531 Roundtrip, found 1 day ago

$531

Roundtrip

found 1 day ago

Select United flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $531 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$531 Roundtrip, found 1 day ago

$531

Roundtrip

found 1 day ago

Select United flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $531 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$535 Roundtrip, found 1 day ago

$535

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $535 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$541 Roundtrip, found 1 day ago

$541

Roundtrip

found 1 day ago

Select United flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $541 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$541 Roundtrip, found 1 day ago

$541

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $541 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$551 Roundtrip, found 1 day ago

$551

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $551 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$551 Roundtrip, found 1 day ago

$551

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $551 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$554 Roundtrip, found 1 day ago

$554

Roundtrip

found 1 day ago

Select United flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $554 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$561 Roundtrip, found 1 day ago

$561

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $561 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$561 Roundtrip, found 1 day ago

$561

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $561 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$645 Roundtrip, found 1 day ago

$645

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $645 found 1 day ago

Thu, May 22 - Fri, May 23

ORD

O'Hare Intl.

BDL

Bradley Intl.

$719 Roundtrip, found 1 day ago

$719

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Thu, May 22 from O'Hare Intl. to Bradley Intl., returning Fri, May 23, priced at $719 found 1 day ago