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.

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$137 Roundtrip, found 5 hours ago

$137

Roundtrip

found 5 hours ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $137 found 5 hours ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$172 Roundtrip, found 5 hours ago

$172

Roundtrip

found 5 hours ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $172 found 5 hours ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$187 Roundtrip, found 5 hours ago

$187

Roundtrip

found 5 hours ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $187 found 5 hours ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$191 Roundtrip, found 5 hours ago

$191

Roundtrip

found 5 hours ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $191 found 5 hours ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$205 Roundtrip, found 5 hours ago

$205

Roundtrip

found 5 hours ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $205 found 5 hours ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$207 Roundtrip, found 5 hours ago

$207

Roundtrip

found 5 hours ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $207 found 5 hours ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$209 Roundtrip, found 5 hours ago

$209

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $209 found 5 hours ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$212 Roundtrip, found 5 hours ago

$212

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $212 found 5 hours ago

Tue, Oct 14 - Sat, Oct 18

MDW

Midway Intl.

BDL

Bradley Intl.

$217 Roundtrip, found 6 days ago

$217

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Oct 14 from Midway Intl. to Bradley Intl., returning Sat, Oct 18, priced at $217 found 6 days ago

Tue, Oct 14 - Thu, Oct 16

ORD

O'Hare Intl.

BDL

Bradley Intl.

$217 Roundtrip, found 3 days ago

$217

Roundtrip

found 3 days ago

Select American Airlines flight, departing Tue, Oct 14 from O'Hare Intl. to Bradley Intl., returning Thu, Oct 16, priced at $217 found 3 days ago

Wed, Oct 15 - Thu, Oct 16

ORD

O'Hare Intl.

BDL

Bradley Intl.

$222 Roundtrip, found 3 days ago

$222

Roundtrip

found 3 days ago

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Bradley Intl., returning Thu, Oct 16, priced at $222 found 3 days ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$222 Roundtrip, found 5 hours ago

$222

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $222 found 5 hours ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$226 Roundtrip, found 5 hours ago

$226

Roundtrip

found 5 hours ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $226 found 5 hours ago

Thu, Oct 16 - Sun, Oct 19

ORD

O'Hare Intl.

BDL

Bradley Intl.

$231 Roundtrip, found 8 hours ago

$231

Roundtrip

found 8 hours ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Sun, Oct 19, priced at $231 found 8 hours ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$234 Roundtrip, found 5 hours ago

$234

Roundtrip

found 5 hours ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $234 found 5 hours ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$236 Roundtrip, found 5 hours ago

$236

Roundtrip

found 5 hours ago

Select JetBlue Airways flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $236 found 5 hours ago

Wed, Oct 15 - Wed, Oct 22

ORD

O'Hare Intl.

BDL

Bradley Intl.

$237 Roundtrip, found 3 days ago

$237

Roundtrip

found 3 days ago

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Bradley Intl., returning Wed, Oct 22, priced at $237 found 3 days ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$240 Roundtrip, found 5 hours ago

$240

Roundtrip

found 5 hours ago

Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $240 found 5 hours ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$244 Roundtrip, found 5 hours ago

$244

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $244 found 5 hours ago

Thu, Oct 16 - Tue, Oct 21

ORD

O'Hare Intl.

BDL

Bradley Intl.

$247 Roundtrip, found 5 hours ago

$247

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $247 found 5 hours ago