Flights from Chicago to Bridgeport

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, Jul 1 - Wed, Jul 2

MDW

Midway Intl.

DFW

Dallas-Fort Worth Intl.

$119 Roundtrip, found 6 days ago

$119

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Tue, Jul 1 from Midway Intl. to Dallas-Fort Worth Intl., returning Wed, Jul 2, priced at $119 found 6 days ago

Tue, Jul 1 - Mon, Jul 7

MDW

Midway Intl.

DFW

Dallas-Fort Worth Intl.

$122 Roundtrip, found 6 days ago

$122

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Tue, Jul 1 from Midway Intl. to Dallas-Fort Worth Intl., returning Mon, Jul 7, priced at $122 found 6 days ago

Fri, Jul 4 - Mon, Jul 7

MDW

Midway Intl.

DFW

Dallas-Fort Worth Intl.

$123 Roundtrip, found 6 days ago

$123

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Fri, Jul 4 from Midway Intl. to Dallas-Fort Worth Intl., returning Mon, Jul 7, priced at $123 found 6 days ago

Sat, Jun 28 - Wed, Jul 2

MDW

Midway Intl.

DFW

Dallas-Fort Worth Intl.

$126 Roundtrip, found 6 days ago

$126

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sat, Jun 28 from Midway Intl. to Dallas-Fort Worth Intl., returning Wed, Jul 2, priced at $126 found 6 days ago

Sat, Jun 28 - Mon, Jul 7

MDW

Midway Intl.

DFW

Dallas-Fort Worth Intl.

$129 Roundtrip, found 6 days ago

$129

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sat, Jun 28 from Midway Intl. to Dallas-Fort Worth Intl., returning Mon, Jul 7, priced at $129 found 6 days ago

Sun, Jun 29 - Fri, Jul 4

ORD

O'Hare Intl.

DFW

Dallas-Fort Worth Intl.

$131 Roundtrip, found 6 days ago

$131

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sun, Jun 29 from O'Hare Intl. to Dallas-Fort Worth Intl., returning Fri, Jul 4, priced at $131 found 6 days ago

Mon, Jun 30 - Mon, Jul 7

MDW

Midway Intl.

DFW

Dallas-Fort Worth Intl.

$132 Roundtrip, found 6 days ago

$132

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Mon, Jun 30 from Midway Intl. to Dallas-Fort Worth Intl., returning Mon, Jul 7, priced at $132 found 6 days ago

Fri, Jun 20 - Sun, Jun 22

ORD

O'Hare Intl.

DFW

Dallas-Fort Worth Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Jun 20 from O'Hare Intl. to Dallas-Fort Worth Intl., returning Sun, Jun 22, priced at $137 found 1 day ago

Fri, Jun 20 - Sun, Jun 22

ORD

O'Hare Intl.

DFW

Dallas-Fort Worth Intl.

$146 Roundtrip, found 1 day ago

$146

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Fri, Jun 20 from O'Hare Intl. to Dallas-Fort Worth Intl., returning Sun, Jun 22, priced at $146 found 1 day ago

Tue, Jul 1 - Tue, Jul 8

MDW

Midway Intl.

DFW

Dallas-Fort Worth Intl.

$147 Roundtrip, found 6 days ago

$147

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Tue, Jul 1 from Midway Intl. to Dallas-Fort Worth Intl., returning Tue, Jul 8, priced at $147 found 6 days ago

Tue, Jul 1 - Sat, Jul 5

ORD

O'Hare Intl.

DFW

Dallas-Fort Worth Intl.

$148 Roundtrip, found 6 days ago

$148

Roundtrip

found 6 days ago

Select United flight, departing Tue, Jul 1 from O'Hare Intl. to Dallas-Fort Worth Intl., returning Sat, Jul 5, priced at $148 found 6 days ago

Sat, Jun 28 - Tue, Jul 8

MDW

Midway Intl.

DFW

Dallas-Fort Worth Intl.

$154 Roundtrip, found 6 days ago

$154

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sat, Jun 28 from Midway Intl. to Dallas-Fort Worth Intl., returning Tue, Jul 8, priced at $154 found 6 days ago

Mon, Jun 30 - Tue, Jul 8

MDW

Midway Intl.

DFW

Dallas-Fort Worth Intl.

$157 Roundtrip, found 6 days ago

$157

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Mon, Jun 30 from Midway Intl. to Dallas-Fort Worth Intl., returning Tue, Jul 8, priced at $157 found 6 days ago

Tue, Jul 1 - Thu, Jul 3

MDW

Midway Intl.

DFW

Dallas-Fort Worth Intl.

$160 Roundtrip, found 6 days ago

$160

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Tue, Jul 1 from Midway Intl. to Dallas-Fort Worth Intl., returning Thu, Jul 3, priced at $160 found 6 days ago

Tue, Jul 1 - Sat, Jul 5

ORD

O'Hare Intl.

DFW

Dallas-Fort Worth Intl.

$161 Roundtrip, found 6 days ago

$161

Roundtrip

found 6 days ago

Select American Airlines flight, departing Tue, Jul 1 from O'Hare Intl. to Dallas-Fort Worth Intl., returning Sat, Jul 5, priced at $161 found 6 days ago

Sat, Jun 14 - Sun, Jun 15

MDW

Midway Intl.

DAL

Love Field

$197 Roundtrip, found 3 days ago

$197

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Jun 14 from Midway Intl. to Love Field, returning Sun, Jun 15, priced at $197 found 3 days ago

Tue, Jul 1 - Sat, Jul 5

ORD

O'Hare Intl.

DAL

Love Field

$197 Roundtrip, found 6 days ago

$197

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Jul 1 from O'Hare Intl. to Love Field, returning Sat, Jul 5, priced at $197 found 6 days ago

Tue, Jul 1 - Sat, Jul 5

ORD

O'Hare Intl.

DFW

Dallas-Fort Worth Intl.

$197 Roundtrip, found 6 days ago

$197

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Jul 1 from O'Hare Intl. to Dallas-Fort Worth Intl., returning Sat, Jul 5, priced at $197 found 6 days ago

Fri, Jun 20 - Sun, Jun 22

ORD

O'Hare Intl.

DFW

Dallas-Fort Worth Intl.

$209 Roundtrip, found 1 day ago

$209

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Jun 20 from O'Hare Intl. to Dallas-Fort Worth Intl., returning Sun, Jun 22, priced at $209 found 1 day ago

Fri, Jun 20 - Sun, Jun 22

ORD

O'Hare Intl.

DFW

Dallas-Fort Worth Intl.

$227 Roundtrip, found 1 day ago

$227

Roundtrip

found 1 day ago

Select United flight, departing Fri, Jun 20 from O'Hare Intl. to Dallas-Fort Worth Intl., returning Sun, Jun 22, priced at $227 found 1 day ago