Flights from Chicago to Cheshire

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.

Wed, Sep 17 - Sun, Sep 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$131 Roundtrip, found 1 day ago

$131

Roundtrip

found 1 day ago

Select United flight, departing Wed, Sep 17 from O'Hare Intl. to Bradley Intl., returning Sun, Sep 21, priced at $131 found 1 day ago

Wed, Sep 17 - Sun, Sep 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$155 Roundtrip, found 1 day ago

$155

Roundtrip

found 1 day ago

Select United flight, departing Wed, Sep 17 from O'Hare Intl. to Bradley Intl., returning Sun, Sep 21, priced at $155 found 1 day ago

Wed, Sep 17 - Sun, Sep 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$159 Roundtrip, found 1 day ago

$159

Roundtrip

found 1 day ago

Select United flight, departing Wed, Sep 17 from O'Hare Intl. to Bradley Intl., returning Sun, Sep 21, priced at $159 found 1 day ago

Wed, Sep 17 - Sun, Sep 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$165 Roundtrip, found 1 day ago

$165

Roundtrip

found 1 day ago

Select United flight, departing Wed, Sep 17 from O'Hare Intl. to Bradley Intl., returning Sun, Sep 21, priced at $165 found 1 day ago

Wed, Sep 17 - Sun, Sep 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$166 Roundtrip, found 1 day ago

$166

Roundtrip

found 1 day ago

Select United flight, departing Wed, Sep 17 from O'Hare Intl. to Bradley Intl., returning Sun, Sep 21, priced at $166 found 1 day ago

Wed, Sep 17 - Sun, Sep 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$167 Roundtrip, found 1 day ago

$167

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Sep 17 from O'Hare Intl. to Bradley Intl., returning Sun, Sep 21, priced at $167 found 1 day ago

Sat, Oct 18 - Mon, Oct 20

ORD

O'Hare Intl.

BDL

Bradley Intl.

$167 Roundtrip, found 1 day ago

$167

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Bradley Intl., returning Mon, Oct 20, priced at $167 found 1 day ago

Tue, Oct 7 - Wed, Oct 15

ORD

O'Hare Intl.

BDL

Bradley Intl.

$177 Roundtrip, found 6 days ago

$177

Roundtrip

found 6 days ago

Select American Airlines flight, departing Tue, Oct 7 from O'Hare Intl. to Bradley Intl., returning Wed, Oct 15, priced at $177 found 6 days ago

Wed, Sep 17 - Sun, Sep 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$183 Roundtrip, found 1 day ago

$183

Roundtrip

found 1 day ago

Select United flight, departing Wed, Sep 17 from O'Hare Intl. to Bradley Intl., returning Sun, Sep 21, priced at $183 found 1 day ago

Tue, Oct 7 - Wed, Oct 15

ORD

O'Hare Intl.

BDL

Bradley Intl.

$184 Roundtrip, found 6 days ago

$184

Roundtrip

found 6 days ago

Select United flight, departing Tue, Oct 7 from O'Hare Intl. to Bradley Intl., returning Wed, Oct 15, priced at $184 found 6 days ago

Tue, Oct 7 - Wed, Oct 15

ORD

O'Hare Intl.

BDL

Bradley Intl.

$187 Roundtrip, found 6 days ago

$187

Roundtrip

found 6 days ago

Select United flight, departing Tue, Oct 7 from O'Hare Intl. to Bradley Intl., returning Wed, Oct 15, priced at $187 found 6 days ago

Wed, Sep 17 - Sun, Sep 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$190 Roundtrip, found 1 day ago

$190

Roundtrip

found 1 day ago

Select United flight, departing Wed, Sep 17 from O'Hare Intl. to Bradley Intl., returning Sun, Sep 21, priced at $190 found 1 day ago

Wed, Sep 17 - Sun, Sep 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$192 Roundtrip, found 1 day ago

$192

Roundtrip

found 1 day ago

Select United flight, departing Wed, Sep 17 from O'Hare Intl. to Bradley Intl., returning Sun, Sep 21, priced at $192 found 1 day ago

Tue, Oct 7 - Wed, Oct 15

ORD

O'Hare Intl.

BDL

Bradley Intl.

$194 Roundtrip, found 6 days ago

$194

Roundtrip

found 6 days ago

Select United flight, departing Tue, Oct 7 from O'Hare Intl. to Bradley Intl., returning Wed, Oct 15, priced at $194 found 6 days ago

Thu, Sep 18 - Sat, Sep 20

ORD

O'Hare Intl.

BDL

Bradley Intl.

$195 Roundtrip, found 1 day ago

$195

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, Sep 18 from O'Hare Intl. to Bradley Intl., returning Sat, Sep 20, priced at $195 found 1 day ago

Tue, Oct 7 - Wed, Oct 15

ORD

O'Hare Intl.

BDL

Bradley Intl.

$197 Roundtrip, found 6 days ago

$197

Roundtrip

found 6 days ago

Select United flight, departing Tue, Oct 7 from O'Hare Intl. to Bradley Intl., returning Wed, Oct 15, priced at $197 found 6 days ago

Wed, Sep 17 - Sun, Sep 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$200 Roundtrip, found 1 day ago

$200

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Sep 17 from O'Hare Intl. to Bradley Intl., returning Sun, Sep 21, priced at $200 found 1 day ago

Wed, Sep 17 - Sun, Sep 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$200 Roundtrip, found 1 day ago

$200

Roundtrip

found 1 day ago

Select United flight, departing Wed, Sep 17 from O'Hare Intl. to Bradley Intl., returning Sun, Sep 21, priced at $200 found 1 day ago

Wed, Oct 15 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$203 Roundtrip, found 1 day ago

$203

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $203 found 1 day ago

Tue, Oct 7 - Wed, Oct 15

ORD

O'Hare Intl.

BDL

Bradley Intl.

$283 Roundtrip, found 6 days ago

$283

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Tue, Oct 7 from O'Hare Intl. to Bradley Intl., returning Wed, Oct 15, priced at $283 found 6 days ago