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 1 day ago

$197

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jul 22 from Bradley Intl. to Midway Intl., returning Tue, Jul 29, priced at $197 found 1 day ago

Tue, Sep 23 - Tue, Sep 30

BDL

Bradley Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 2 hours ago

$197

Roundtrip

found 2 hours ago

Select Delta flight, departing Tue, Sep 23 from Bradley Intl. to O'Hare Intl., returning Tue, Sep 30, priced at $197 found 2 hours ago

Fri, Oct 17 - Sun, Oct 19

BDL

Bradley Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 23 hours ago

$197

Roundtrip

found 23 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 23 hours ago

Tue, Sep 23 - Thu, Sep 25

BDL

Bradley Intl.

ORD

O'Hare Intl.

$207 Roundtrip, found 2 hours ago

$207

Roundtrip

found 2 hours ago

Select United flight, departing Tue, Sep 23 from Bradley Intl. to O'Hare Intl., returning Thu, Sep 25, priced at $207 found 2 hours ago

Sun, Sep 21 - Tue, Sep 30

BDL

Bradley Intl.

ORD

O'Hare Intl.

$207 Roundtrip, found 2 hours ago

$207

Roundtrip

found 2 hours ago

Select American Airlines flight, departing Sun, Sep 21 from Bradley Intl. to O'Hare Intl., returning Tue, Sep 30, priced at $207 found 2 hours ago

Sat, Jul 26 - Sun, Jul 27

BDL

Bradley Intl.

ORD

O'Hare Intl.

$215 Roundtrip, found 1 day ago

$215

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jul 26 from Bradley Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $215 found 1 day ago

Thu, Sep 18 - Sat, Sep 27

BDL

Bradley Intl.

ORD

O'Hare Intl.

$225 Roundtrip, found 2 hours ago

$225

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Thu, Sep 18 from Bradley Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $225 found 2 hours ago

Tue, Jul 22 - Thu, Jul 24

BDL

Bradley Intl.

ORD

O'Hare Intl.

$227 Roundtrip, found 1 day ago

$227

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Jul 22 from Bradley Intl. to O'Hare Intl., returning Thu, Jul 24, priced at $227 found 1 day ago

Thu, Jul 24 - Sun, Jul 27

BDL

Bradley Intl.

ORD

O'Hare Intl.

$230 Roundtrip, found 1 day ago

$230

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Thu, Jul 24 from Bradley Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $230 found 1 day ago

Thu, Sep 18 - Fri, Sep 26

BDL

Bradley Intl.

ORD

O'Hare Intl.

$235 Roundtrip, found 2 hours ago

$235

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Thu, Sep 18 from Bradley Intl. to O'Hare Intl., returning Fri, Sep 26, priced at $235 found 2 hours ago

Thu, Jul 24 - Sat, Jul 26

BDL

Bradley Intl.

ORD

O'Hare Intl.

$240 Roundtrip, found 1 day ago

$240

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Thu, Jul 24 from Bradley Intl. to O'Hare Intl., returning Sat, Jul 26, priced at $240 found 1 day ago

Thu, Sep 18 - Thu, Sep 25

BDL

Bradley Intl.

ORD

O'Hare Intl.

$242 Roundtrip, found 2 hours ago

$242

Roundtrip

found 2 hours ago

Select United flight, departing Thu, Sep 18 from Bradley Intl. to O'Hare Intl., returning Thu, Sep 25, priced at $242 found 2 hours ago

Wed, Sep 17 - Tue, Sep 30

BDL

Bradley Intl.

ORD

O'Hare Intl.

$245 Roundtrip, found 2 hours ago

$245

Roundtrip

found 2 hours ago

Select Delta flight, departing Wed, Sep 17 from Bradley Intl. to O'Hare Intl., returning Tue, Sep 30, priced at $245 found 2 hours ago

Sat, Jul 26 - Mon, Jul 28

BDL

Bradley Intl.

ORD

O'Hare Intl.

$245 Roundtrip, found 1 day ago

$245

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jul 26 from Bradley Intl. to O'Hare Intl., returning Mon, Jul 28, priced at $245 found 1 day ago

Sat, Sep 20 - Sat, Sep 27

BDL

Bradley Intl.

ORD

O'Hare Intl.

$250 Roundtrip, found 2 hours ago

$250

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Sat, Sep 20 from Bradley Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $250 found 2 hours ago

Mon, Jul 21 - Sun, Jul 27

BDL

Bradley Intl.

ORD

O'Hare Intl.

$250 Roundtrip, found 1 day ago

$250

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Mon, Jul 21 from Bradley Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $250 found 1 day ago

Fri, Oct 17 - Sun, Oct 19

BDL

Bradley Intl.

ORD

O'Hare Intl.

$251 Roundtrip, found 23 hours ago

$251

Roundtrip

found 23 hours ago

Select United flight, departing Fri, Oct 17 from Bradley Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $251 found 23 hours ago

Fri, Oct 17 - Sun, Oct 19

BDL

Bradley Intl.

ORD

O'Hare Intl.

$253 Roundtrip, found 23 hours ago

$253

Roundtrip

found 23 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 23 hours ago

Sat, Sep 20 - Sat, Sep 27

BDL

Bradley Intl.

ORD

O'Hare Intl.

$254 Roundtrip, found 2 hours ago

$254

Roundtrip

found 2 hours ago

Select United flight, departing Sat, Sep 20 from Bradley Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $254 found 2 hours ago

Wed, Jul 23 - Tue, Jul 29

BDL

Bradley Intl.

ORD

O'Hare Intl.

$319 Roundtrip, found 1 day ago

$319

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Wed, Jul 23 from Bradley Intl. to O'Hare Intl., returning Tue, Jul 29, priced at $319 found 1 day ago