Flights from Chicago to Valparaiso

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.

Mon, Jul 28 - Mon, Aug 4

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$287 Roundtrip, found 1 day ago

$287

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Jul 28 from O'Hare Intl. to Northwest Florida Regional, returning Mon, Aug 4, priced at $287 found 1 day ago

Mon, Jul 28 - Sun, Aug 3

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$306 Roundtrip, found 1 day ago

$306

Roundtrip

found 1 day ago

Select Delta flight, departing Mon, Jul 28 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Aug 3, priced at $306 found 1 day ago

Mon, Jul 28 - Sat, Aug 2

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$337 Roundtrip, found 1 day ago

$337

Roundtrip

found 1 day ago

Select Delta flight, departing Mon, Jul 28 from O'Hare Intl. to Northwest Florida Regional, returning Sat, Aug 2, priced at $337 found 1 day ago

Sun, Jul 27 - Sun, Aug 3

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$377 Roundtrip, found 1 day ago

$377

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Jul 27 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Aug 3, priced at $377 found 1 day ago

Tue, Jul 29 - Mon, Aug 4

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$383 Roundtrip, found 1 day ago

$383

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jul 29 from O'Hare Intl. to Northwest Florida Regional, returning Mon, Aug 4, priced at $383 found 1 day ago

Sun, Jul 27 - Sat, Aug 2

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$387 Roundtrip, found 1 day ago

$387

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Jul 27 from O'Hare Intl. to Northwest Florida Regional, returning Sat, Aug 2, priced at $387 found 1 day ago

Sun, Jul 27 - Fri, Aug 1

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$416 Roundtrip, found 1 day ago

$416

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Jul 27 from O'Hare Intl. to Northwest Florida Regional, returning Fri, Aug 1, priced at $416 found 1 day ago

Tue, Jul 29 - Sun, Aug 3

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$425 Roundtrip, found 1 day ago

$425

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jul 29 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Aug 3, priced at $425 found 1 day ago

Tue, Jul 29 - Fri, Aug 1

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$435 Roundtrip, found 1 day ago

$435

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jul 29 from O'Hare Intl. to Northwest Florida Regional, returning Fri, Aug 1, priced at $435 found 1 day ago

Tue, Jul 29 - Sat, Aug 2

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$442 Roundtrip, found 1 day ago

$442

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jul 29 from O'Hare Intl. to Northwest Florida Regional, returning Sat, Aug 2, priced at $442 found 1 day ago

Sun, Jul 27 - Fri, Aug 1

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$448 Roundtrip, found 1 day ago

$448

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Jul 27 from O'Hare Intl. to Northwest Florida Regional, returning Fri, Aug 1, priced at $448 found 1 day ago

Sun, Jul 27 - Fri, Aug 1

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$457 Roundtrip, found 1 day ago

$457

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Jul 27 from O'Hare Intl. to Northwest Florida Regional, returning Fri, Aug 1, priced at $457 found 1 day ago

Sun, Jul 27 - Fri, Aug 1

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$459 Roundtrip, found 1 day ago

$459

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Jul 27 from O'Hare Intl. to Northwest Florida Regional, returning Fri, Aug 1, priced at $459 found 1 day ago

Sun, Jul 27 - Fri, Aug 1

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$461 Roundtrip, found 1 day ago

$461

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Jul 27 from O'Hare Intl. to Northwest Florida Regional, returning Fri, Aug 1, priced at $461 found 1 day ago

Sun, Jul 27 - Fri, Aug 1

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$486 Roundtrip, found 1 day ago

$486

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Jul 27 from O'Hare Intl. to Northwest Florida Regional, returning Fri, Aug 1, priced at $486 found 1 day ago

Sun, Jul 27 - Fri, Aug 1

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$490 Roundtrip, found 1 day ago

$490

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Jul 27 from O'Hare Intl. to Northwest Florida Regional, returning Fri, Aug 1, priced at $490 found 1 day ago

Sun, Jul 27 - Fri, Aug 1

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$492 Roundtrip, found 1 day ago

$492

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Jul 27 from O'Hare Intl. to Northwest Florida Regional, returning Fri, Aug 1, priced at $492 found 1 day ago

Sun, Jul 27 - Fri, Aug 1

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$496 Roundtrip, found 1 day ago

$496

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Jul 27 from O'Hare Intl. to Northwest Florida Regional, returning Fri, Aug 1, priced at $496 found 1 day ago

Sun, Jul 27 - Fri, Aug 1

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$507 Roundtrip, found 1 day ago

$507

Roundtrip

found 1 day ago

Select Delta flight, departing Sun, Jul 27 from O'Hare Intl. to Northwest Florida Regional, returning Fri, Aug 1, priced at $507 found 1 day ago

Sun, Jul 27 - Fri, Aug 1

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$518 Roundtrip, found 1 day ago

$518

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Jul 27 from O'Hare Intl. to Northwest Florida Regional, returning Fri, Aug 1, priced at $518 found 1 day ago