Flights from Chicago to Essex

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, Oct 14 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$207 Roundtrip, found 1 day ago

$207

Roundtrip

found 1 day ago

Select United flight, departing Tue, Oct 14 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $207 found 1 day ago

Tue, Oct 14 - Sat, Oct 18

MDW

Midway Intl.

BDL

Bradley Intl.

$217 Roundtrip, found 4 days ago

$217

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Oct 14 from Midway Intl. to Bradley Intl., returning Sat, Oct 18, priced at $217 found 4 days ago

Tue, Oct 14 - Thu, Oct 16

ORD

O'Hare Intl.

BDL

Bradley Intl.

$217 Roundtrip, found 1 day ago

$217

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Oct 14 from O'Hare Intl. to Bradley Intl., returning Thu, Oct 16, priced at $217 found 1 day ago

Thu, Oct 16 - Sun, Oct 19

ORD

O'Hare Intl.

BDL

Bradley Intl.

$219 Roundtrip, found 1 day ago

$219

Roundtrip

found 1 day ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Sun, Oct 19, priced at $219 found 1 day ago

Wed, Oct 15 - Thu, Oct 16

ORD

O'Hare Intl.

BDL

Bradley Intl.

$222 Roundtrip, found 1 day ago

$222

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Bradley Intl., returning Thu, Oct 16, priced at $222 found 1 day ago

Mon, Nov 24 - Mon, Nov 24

ORD

O'Hare Intl.

BDL

Bradley Intl.

$231 Roundtrip, found 4 days ago

$231

Roundtrip

found 4 days ago

Select United flight, departing Mon, Nov 24 from O'Hare Intl. to Bradley Intl., returning Mon, Nov 24, priced at $231 found 4 days ago

Wed, Oct 15 - Wed, Oct 22

ORD

O'Hare Intl.

BDL

Bradley Intl.

$237 Roundtrip, found 1 day ago

$237

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Bradley Intl., returning Wed, Oct 22, priced at $237 found 1 day ago

Mon, Nov 24 - Mon, Nov 24

ORD

O'Hare Intl.

BDL

Bradley Intl.

$241 Roundtrip, found 4 days ago

$241

Roundtrip

found 4 days ago

Select United flight, departing Mon, Nov 24 from O'Hare Intl. to Bradley Intl., returning Mon, Nov 24, priced at $241 found 4 days ago

Thu, Oct 16 - Thu, Oct 16

ORD

O'Hare Intl.

BDL

Bradley Intl.

$242 Roundtrip, found 4 days ago

$242

Roundtrip

found 4 days ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Thu, Oct 16, priced at $242 found 4 days ago

Thu, Oct 16 - Sun, Oct 19

ORD

O'Hare Intl.

BDL

Bradley Intl.

$243 Roundtrip, found 1 day ago

$243

Roundtrip

found 1 day ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Sun, Oct 19, priced at $243 found 1 day ago

Tue, Oct 14 - Sat, Oct 18

ORD

O'Hare Intl.

BDL

Bradley Intl.

$247 Roundtrip, found 1 day ago

$247

Roundtrip

found 1 day ago

Select United flight, departing Tue, Oct 14 from O'Hare Intl. to Bradley Intl., returning Sat, Oct 18, priced at $247 found 1 day ago

Tue, Oct 14 - Fri, Oct 17

ORD

O'Hare Intl.

BDL

Bradley Intl.

$254 Roundtrip, found 1 day ago

$254

Roundtrip

found 1 day ago

Select United flight, departing Tue, Oct 14 from O'Hare Intl. to Bradley Intl., returning Fri, Oct 17, priced at $254 found 1 day ago

Tue, Oct 14 - Sun, Oct 19

MDW

Midway Intl.

BDL

Bradley Intl.

$268 Roundtrip, found 4 days ago

$268

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Oct 14 from Midway Intl. to Bradley Intl., returning Sun, Oct 19, priced at $268 found 4 days ago

Thu, Oct 16 - Thu, Oct 16

ORD

O'Hare Intl.

BDL

Bradley Intl.

$269 Roundtrip, found 1 day ago

$269

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Thu, Oct 16, priced at $269 found 1 day ago

Thu, Oct 16 - Sun, Oct 19

ORD

O'Hare Intl.

BDL

Bradley Intl.

$276 Roundtrip, found 1 day ago

$276

Roundtrip

found 1 day ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Sun, Oct 19, priced at $276 found 1 day ago

Thu, Oct 16 - Sun, Oct 19

ORD

O'Hare Intl.

BDL

Bradley Intl.

$276 Roundtrip, found 1 day ago

$276

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Sun, Oct 19, priced at $276 found 1 day ago

Thu, Oct 16 - Sun, Oct 19

ORD

O'Hare Intl.

BDL

Bradley Intl.

$277 Roundtrip, found 1 day ago

$277

Roundtrip

found 1 day ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Sun, Oct 19, priced at $277 found 1 day ago

Thu, Oct 16 - Sun, Oct 19

ORD

O'Hare Intl.

BDL

Bradley Intl.

$278 Roundtrip, found 1 day ago

$278

Roundtrip

found 1 day ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Sun, Oct 19, priced at $278 found 1 day ago

Thu, Oct 16 - Sun, Oct 19

MDW

Midway Intl.

BDL

Bradley Intl.

$312 Roundtrip, found 4 days ago

$312

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Thu, Oct 16 from Midway Intl. to Bradley Intl., returning Sun, Oct 19, priced at $312 found 4 days ago

Thu, Oct 16 - Sun, Oct 19

ORD

O'Hare Intl.

BDL

Bradley Intl.

$330 Roundtrip, found 1 day ago

$330

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Sun, Oct 19, priced at $330 found 1 day ago