Flights from Windsor Locks to Chicago

Cheapest flights from Windsor Locks

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 22 - Tue, Jul 29

BDL

Bradley Intl.

MDW

Midway Intl.

$197 Roundtrip, found 20 hours ago

$197

Roundtrip

found 20 hours ago

Select Delta flight, departing Tue, Jul 22 from Bradley Intl. to Midway Intl., returning Tue, Jul 29, priced at $197 found 20 hours ago

Sun, Oct 5 - Tue, Oct 21

BDL

Bradley Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 6 days ago

$197

Roundtrip

found 6 days ago

Select Delta flight, departing Sun, Oct 5 from Bradley Intl. to O'Hare Intl., returning Tue, Oct 21, priced at $197 found 6 days ago

Fri, Oct 17 - Sun, Oct 19

BDL

Bradley Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 19 hours ago

$197

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Fri, Oct 17 from Bradley Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $197 found 19 hours ago

Thu, Oct 2 - Tue, Oct 21

BDL

Bradley Intl.

ORD

O'Hare Intl.

$207 Roundtrip, found 6 days ago

$207

Roundtrip

found 6 days ago

Select American Airlines flight, departing Thu, Oct 2 from Bradley Intl. to O'Hare Intl., returning Tue, Oct 21, priced at $207 found 6 days ago

Sat, Jul 26 - Sun, Jul 27

BDL

Bradley Intl.

ORD

O'Hare Intl.

$215 Roundtrip, found 20 hours ago

$215

Roundtrip

found 20 hours ago

Select Spirit Airlines flight, departing Sat, Jul 26 from Bradley Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $215 found 20 hours ago

Tue, Jul 22 - Thu, Jul 24

BDL

Bradley Intl.

ORD

O'Hare Intl.

$227 Roundtrip, found 20 hours ago

$227

Roundtrip

found 20 hours ago

Select American Airlines flight, departing Tue, Jul 22 from Bradley Intl. to O'Hare Intl., returning Thu, Jul 24, priced at $227 found 20 hours ago

Thu, Jul 24 - Sun, Jul 27

BDL

Bradley Intl.

ORD

O'Hare Intl.

$230 Roundtrip, found 20 hours ago

$230

Roundtrip

found 20 hours ago

Select Spirit Airlines flight, departing Thu, Jul 24 from Bradley Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $230 found 20 hours ago

Thu, Jul 24 - Sat, Jul 26

BDL

Bradley Intl.

ORD

O'Hare Intl.

$240 Roundtrip, found 20 hours ago

$240

Roundtrip

found 20 hours ago

Select Spirit Airlines flight, departing Thu, Jul 24 from Bradley Intl. to O'Hare Intl., returning Sat, Jul 26, priced at $240 found 20 hours ago

Wed, Oct 1 - Tue, Oct 21

BDL

Bradley Intl.

ORD

O'Hare Intl.

$245 Roundtrip, found 6 days ago

$245

Roundtrip

found 6 days ago

Select Delta flight, departing Wed, Oct 1 from Bradley Intl. to O'Hare Intl., returning Tue, Oct 21, priced at $245 found 6 days ago

Sat, Jul 26 - Mon, Jul 28

BDL

Bradley Intl.

ORD

O'Hare Intl.

$245 Roundtrip, found 20 hours ago

$245

Roundtrip

found 20 hours ago

Select Spirit Airlines flight, departing Sat, Jul 26 from Bradley Intl. to O'Hare Intl., returning Mon, Jul 28, priced at $245 found 20 hours ago

Mon, Jul 21 - Sun, Jul 27

BDL

Bradley Intl.

ORD

O'Hare Intl.

$250 Roundtrip, found 20 hours ago

$250

Roundtrip

found 20 hours ago

Select Spirit Airlines flight, departing Mon, Jul 21 from Bradley Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $250 found 20 hours ago

Fri, Oct 17 - Sun, Oct 19

BDL

Bradley Intl.

ORD

O'Hare Intl.

$251 Roundtrip, found 19 hours ago

$251

Roundtrip

found 19 hours ago

Select United flight, departing Fri, Oct 17 from Bradley Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $251 found 19 hours ago

Fri, Oct 17 - Sun, Oct 19

BDL

Bradley Intl.

ORD

O'Hare Intl.

$253 Roundtrip, found 19 hours ago

$253

Roundtrip

found 19 hours ago

Select American Airlines flight, departing Fri, Oct 17 from Bradley Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $253 found 19 hours ago

Fri, Jul 25 - Sat, Jul 26

BDL

Bradley Intl.

ORD

O'Hare Intl.

$255 Roundtrip, found 20 hours ago

$255

Roundtrip

found 20 hours ago

Select Spirit Airlines flight, departing Fri, Jul 25 from Bradley Intl. to O'Hare Intl., returning Sat, Jul 26, priced at $255 found 20 hours ago

Thu, Jul 24 - Mon, Jul 28

BDL

Bradley Intl.

ORD

O'Hare Intl.

$260 Roundtrip, found 20 hours ago

$260

Roundtrip

found 20 hours ago

Select Spirit Airlines flight, departing Thu, Jul 24 from Bradley Intl. to O'Hare Intl., returning Mon, Jul 28, priced at $260 found 20 hours ago

Fri, Oct 17 - Sun, Oct 19

BDL

Bradley Intl.

ORD

O'Hare Intl.

$261 Roundtrip, found 19 hours ago

$261

Roundtrip

found 19 hours ago

Select American Airlines flight, departing Fri, Oct 17 from Bradley Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $261 found 19 hours ago

Fri, Oct 17 - Sun, Oct 19

BDL

Bradley Intl.

ORD

O'Hare Intl.

$265 Roundtrip, found 19 hours ago

$265

Roundtrip

found 19 hours ago

Select American Airlines flight, departing Fri, Oct 17 from Bradley Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $265 found 19 hours ago

Fri, Oct 17 - Sun, Oct 19

BDL

Bradley Intl.

ORD

O'Hare Intl.

$267 Roundtrip, found 19 hours ago

$267

Roundtrip

found 19 hours ago

Select American Airlines flight, departing Fri, Oct 17 from Bradley Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $267 found 19 hours ago

Mon, Jul 21 - Thu, Jul 24

BDL

Bradley Intl.

ORD

O'Hare Intl.

$270 Roundtrip, found 20 hours ago

$270

Roundtrip

found 20 hours ago

Select Spirit Airlines flight, departing Mon, Jul 21 from Bradley Intl. to O'Hare Intl., returning Thu, Jul 24, priced at $270 found 20 hours ago

Wed, Jul 23 - Tue, Jul 29

BDL

Bradley Intl.

ORD

O'Hare Intl.

$319 Roundtrip, found 20 hours ago

$319

Roundtrip

found 20 hours ago

Select JetBlue Airways flight, departing Wed, Jul 23 from Bradley Intl. to O'Hare Intl., returning Tue, Jul 29, priced at $319 found 20 hours ago