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.

Wed, Sep 3 - Mon, Sep 8

ORD

O'Hare Intl.

HPN

Westchester County

$297 Roundtrip, found 2 days ago

$297

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Sep 3 from O'Hare Intl. to Westchester County, returning Mon, Sep 8, priced at $297 found 2 days ago

Wed, Sep 3 - Sat, Sep 6

ORD

O'Hare Intl.

HPN

Westchester County

$307 Roundtrip, found 2 days ago

$307

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Sep 3 from O'Hare Intl. to Westchester County, returning Sat, Sep 6, priced at $307 found 2 days ago

Sat, Sep 6 - Sat, Sep 13

ORD

O'Hare Intl.

HPN

Westchester County

$317 Roundtrip, found 2 days ago

$317

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Sep 6 from O'Hare Intl. to Westchester County, returning Sat, Sep 13, priced at $317 found 2 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

HPN

Westchester County

$327 Roundtrip, found 2 days ago

$327

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, Sep 4 from O'Hare Intl. to Westchester County, returning Mon, Sep 8, priced at $327 found 2 days ago

Tue, Sep 2 - Mon, Sep 8

ORD

O'Hare Intl.

HPN

Westchester County

$328 Roundtrip, found 2 days ago

$328

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Sep 2 from O'Hare Intl. to Westchester County, returning Mon, Sep 8, priced at $328 found 2 days ago

Thu, Sep 4 - Sat, Sep 6

ORD

O'Hare Intl.

HPN

Westchester County

$337 Roundtrip, found 2 days ago

$337

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, Sep 4 from O'Hare Intl. to Westchester County, returning Sat, Sep 6, priced at $337 found 2 days ago

Tue, Sep 2 - Sat, Sep 6

ORD

O'Hare Intl.

HPN

Westchester County

$338 Roundtrip, found 2 days ago

$338

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Sep 2 from O'Hare Intl. to Westchester County, returning Sat, Sep 6, priced at $338 found 2 days ago

Fri, Sep 5 - Mon, Sep 8

ORD

O'Hare Intl.

HPN

Westchester County

$347 Roundtrip, found 2 days ago

$347

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Sep 5 from O'Hare Intl. to Westchester County, returning Mon, Sep 8, priced at $347 found 2 days ago

Tue, Sep 2 - Fri, Sep 5

ORD

O'Hare Intl.

HPN

Westchester County

$348 Roundtrip, found 2 days ago

$348

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Sep 2 from O'Hare Intl. to Westchester County, returning Fri, Sep 5, priced at $348 found 2 days ago

Fri, Sep 5 - Sat, Sep 6

ORD

O'Hare Intl.

HPN

Westchester County

$357 Roundtrip, found 2 days ago

$357

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Sep 5 from O'Hare Intl. to Westchester County, returning Sat, Sep 6, priced at $357 found 2 days ago

Wed, Sep 3 - Fri, Sep 12

ORD

O'Hare Intl.

HPN

Westchester County

$364 Roundtrip, found 2 days ago

$364

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Sep 3 from O'Hare Intl. to Westchester County, returning Fri, Sep 12, priced at $364 found 2 days ago

Sat, Sep 6 - Fri, Sep 12

ORD

O'Hare Intl.

HPN

Westchester County

$374 Roundtrip, found 2 days ago

$374

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Sep 6 from O'Hare Intl. to Westchester County, returning Fri, Sep 12, priced at $374 found 2 days ago

Thu, Sep 4 - Fri, Sep 5

ORD

O'Hare Intl.

HPN

Westchester County

$379 Roundtrip, found 2 days ago

$379

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, Sep 4 from O'Hare Intl. to Westchester County, returning Fri, Sep 5, priced at $379 found 2 days ago

Fri, Sep 5 - Sat, Sep 6

ORD

O'Hare Intl.

HPN

Westchester County

$380 Roundtrip, found 2 days ago

$380

Roundtrip

found 2 days ago

Select American Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Westchester County, returning Sat, Sep 6, priced at $380 found 2 days ago

Fri, Sep 5 - Sat, Sep 6

ORD

O'Hare Intl.

HPN

Westchester County

$390 Roundtrip, found 2 days ago

$390

Roundtrip

found 2 days ago

Select American Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Westchester County, returning Sat, Sep 6, priced at $390 found 2 days ago

Fri, Sep 5 - Sat, Sep 6

MDW

Midway Intl.

HPN

Westchester County

$400 Roundtrip, found 2 days ago

$400

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Sep 5 from Midway Intl. to Westchester County, returning Sat, Sep 6, priced at $400 found 2 days ago

Tue, Sep 2 - Fri, Sep 12

ORD

O'Hare Intl.

HPN

Westchester County

$400 Roundtrip, found 2 days ago

$400

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Sep 2 from O'Hare Intl. to Westchester County, returning Fri, Sep 12, priced at $400 found 2 days ago

Fri, Sep 5 - Sat, Sep 6

ORD

O'Hare Intl.

HPN

Westchester County

$400 Roundtrip, found 2 days ago

$400

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Sep 5 from O'Hare Intl. to Westchester County, returning Sat, Sep 6, priced at $400 found 2 days ago

Fri, Sep 5 - Sat, Sep 6

ORD

O'Hare Intl.

HPN

Westchester County

$406 Roundtrip, found 2 days ago

$406

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Sep 5 from O'Hare Intl. to Westchester County, returning Sat, Sep 6, priced at $406 found 2 days ago

Fri, Sep 5 - Sat, Sep 6

ORD

O'Hare Intl.

HPN

Westchester County

$410 Roundtrip, found 2 days ago

$410

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Sep 5 from O'Hare Intl. to Westchester County, returning Sat, Sep 6, priced at $410 found 2 days ago