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.

Tue, Jul 29 - Tue, Aug 5

ORD

O'Hare Intl.

BDL

Bradley Intl.

$197 Roundtrip, found 4 days ago

$197

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Jul 29 from O'Hare Intl. to Bradley Intl., returning Tue, Aug 5, priced at $197 found 4 days ago

Tue, Jul 29 - Wed, Aug 6

ORD

O'Hare Intl.

BDL

Bradley Intl.

$207 Roundtrip, found 4 days ago

$207

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Jul 29 from O'Hare Intl. to Bradley Intl., returning Wed, Aug 6, priced at $207 found 4 days ago

Tue, Jul 29 - Sun, Aug 3

ORD

O'Hare Intl.

BDL

Bradley Intl.

$227 Roundtrip, found 4 days ago

$227

Roundtrip

found 4 days ago

Select United flight, departing Tue, Jul 29 from O'Hare Intl. to Bradley Intl., returning Sun, Aug 3, priced at $227 found 4 days ago

Thu, Jul 31 - Tue, Aug 5

ORD

O'Hare Intl.

BDL

Bradley Intl.

$227 Roundtrip, found 4 days ago

$227

Roundtrip

found 4 days ago

Select American Airlines flight, departing Thu, Jul 31 from O'Hare Intl. to Bradley Intl., returning Tue, Aug 5, priced at $227 found 4 days ago

Wed, Jul 30 - Tue, Aug 5

ORD

O'Hare Intl.

BDL

Bradley Intl.

$245 Roundtrip, found 4 days ago

$245

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Jul 30 from O'Hare Intl. to Bradley Intl., returning Tue, Aug 5, priced at $245 found 4 days ago

Thu, Jul 31 - Sat, Aug 2

ORD

O'Hare Intl.

BDL

Bradley Intl.

$245 Roundtrip, found 4 days ago

$245

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Jul 31 from O'Hare Intl. to Bradley Intl., returning Sat, Aug 2, priced at $245 found 4 days ago

Fri, Aug 1 - Sun, Aug 3

ORD

O'Hare Intl.

BDL

Bradley Intl.

$246 Roundtrip, found 4 days ago

$246

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Fri, Aug 1 from O'Hare Intl. to Bradley Intl., returning Sun, Aug 3, priced at $246 found 4 days ago

Tue, Jul 29 - Mon, Aug 4

ORD

O'Hare Intl.

BDL

Bradley Intl.

$247 Roundtrip, found 4 days ago

$247

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Jul 29 from O'Hare Intl. to Bradley Intl., returning Mon, Aug 4, priced at $247 found 4 days ago

Wed, Jul 30 - Wed, Aug 6

ORD

O'Hare Intl.

BDL

Bradley Intl.

$255 Roundtrip, found 4 days ago

$255

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Jul 30 from O'Hare Intl. to Bradley Intl., returning Wed, Aug 6, priced at $255 found 4 days ago

Thu, Jul 31 - Fri, Aug 1

ORD

O'Hare Intl.

BDL

Bradley Intl.

$265 Roundtrip, found 4 days ago

$265

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Jul 31 from O'Hare Intl. to Bradley Intl., returning Fri, Aug 1, priced at $265 found 4 days ago

Fri, Aug 1 - Mon, Aug 4

ORD

O'Hare Intl.

BDL

Bradley Intl.

$266 Roundtrip, found 4 days ago

$266

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Fri, Aug 1 from O'Hare Intl. to Bradley Intl., returning Mon, Aug 4, priced at $266 found 4 days ago

Mon, Aug 4 - Wed, Aug 6

ORD

O'Hare Intl.

BDL

Bradley Intl.

$267 Roundtrip, found 4 days ago

$267

Roundtrip

found 4 days ago

Select American Airlines flight, departing Mon, Aug 4 from O'Hare Intl. to Bradley Intl., returning Wed, Aug 6, priced at $267 found 4 days ago

Fri, Aug 1 - Sun, Aug 3

ORD

O'Hare Intl.

BDL

Bradley Intl.

$275 Roundtrip, found 4 days ago

$275

Roundtrip

found 4 days ago

Select United flight, departing Fri, Aug 1 from O'Hare Intl. to Bradley Intl., returning Sun, Aug 3, priced at $275 found 4 days ago

Thu, Jul 31 - Thu, Aug 7

ORD

O'Hare Intl.

BDL

Bradley Intl.

$277 Roundtrip, found 4 days ago

$277

Roundtrip

found 4 days ago

Select American Airlines flight, departing Thu, Jul 31 from O'Hare Intl. to Bradley Intl., returning Thu, Aug 7, priced at $277 found 4 days ago

Fri, Aug 1 - Sun, Aug 3

ORD

O'Hare Intl.

BDL

Bradley Intl.

$280 Roundtrip, found 4 days ago

$280

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Fri, Aug 1 from O'Hare Intl. to Bradley Intl., returning Sun, Aug 3, priced at $280 found 4 days ago

Fri, Aug 1 - Sun, Aug 3

ORD

O'Hare Intl.

BDL

Bradley Intl.

$285 Roundtrip, found 4 days ago

$285

Roundtrip

found 4 days ago

Select United flight, departing Fri, Aug 1 from O'Hare Intl. to Bradley Intl., returning Sun, Aug 3, priced at $285 found 4 days ago

Fri, Aug 1 - Sun, Aug 3

ORD

O'Hare Intl.

BDL

Bradley Intl.

$292 Roundtrip, found 4 days ago

$292

Roundtrip

found 4 days ago

Select United flight, departing Fri, Aug 1 from O'Hare Intl. to Bradley Intl., returning Sun, Aug 3, priced at $292 found 4 days ago

Fri, Aug 1 - Mon, Aug 4

ORD

O'Hare Intl.

BDL

Bradley Intl.

$293 Roundtrip, found 4 days ago

$293

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Fri, Aug 1 from O'Hare Intl. to Bradley Intl., returning Mon, Aug 4, priced at $293 found 4 days ago

Fri, Aug 1 - Mon, Aug 4

ORD

O'Hare Intl.

BDL

Bradley Intl.

$295 Roundtrip, found 4 days ago

$295

Roundtrip

found 4 days ago

Select American Airlines flight, departing Fri, Aug 1 from O'Hare Intl. to Bradley Intl., returning Mon, Aug 4, priced at $295 found 4 days ago

Wed, Jul 30 - Mon, Aug 4

ORD

O'Hare Intl.

BDL

Bradley Intl.

$299 Roundtrip, found 4 days ago

$299

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Wed, Jul 30 from O'Hare Intl. to Bradley Intl., returning Mon, Aug 4, priced at $299 found 4 days ago