Flights from Chicago to Freeport

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, Sep 18 - Tue, Sep 23

MDW

Midway Intl.

VPS

Northwest Florida Regional

$273 Roundtrip, found 3 hours ago

$273

Roundtrip

found 3 hours ago

Select Delta flight, departing Thu, Sep 18 from Midway Intl. to Northwest Florida Regional, returning Tue, Sep 23, priced at $273 found 3 hours ago

Tue, Sep 16 - Fri, Sep 19

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$309 Roundtrip, found 3 hours ago

$309

Roundtrip

found 3 hours ago

Select Delta flight, departing Tue, Sep 16 from O'Hare Intl. to Northwest Florida Regional, returning Fri, Sep 19, priced at $309 found 3 hours ago

Tue, Sep 16 - Sun, Sep 28

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$311 Roundtrip, found 3 hours ago

$311

Roundtrip

found 3 hours ago

Select Delta flight, departing Tue, Sep 16 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 28, priced at $311 found 3 hours ago

Fri, Sep 19 - Sun, Sep 21

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$321 Roundtrip, found 3 hours ago

$321

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 21, priced at $321 found 3 hours ago

Fri, Sep 19 - Sun, Sep 21

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$323 Roundtrip, found 3 hours ago

$323

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 21, priced at $323 found 3 hours ago

Fri, Sep 19 - Sun, Sep 21

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$344 Roundtrip, found 3 hours ago

$344

Roundtrip

found 3 hours ago

Select Delta flight, departing Fri, Sep 19 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 21, priced at $344 found 3 hours ago

Fri, Sep 19 - Sun, Sep 28

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$347 Roundtrip, found 3 hours ago

$347

Roundtrip

found 3 hours ago

Select Delta flight, departing Fri, Sep 19 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 28, priced at $347 found 3 hours ago

Sun, Sep 21 - Sun, Sep 28

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$349 Roundtrip, found 3 hours ago

$349

Roundtrip

found 3 hours ago

Select Delta flight, departing Sun, Sep 21 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 28, priced at $349 found 3 hours ago

Fri, Sep 19 - Sun, Sep 21

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$351 Roundtrip, found 3 hours ago

$351

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 21, priced at $351 found 3 hours ago

Fri, Sep 19 - Sun, Sep 21

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$374 Roundtrip, found 3 hours ago

$374

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 21, priced at $374 found 3 hours ago

Fri, Sep 19 - Sun, Sep 21

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$375 Roundtrip, found 3 hours ago

$375

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 21, priced at $375 found 3 hours ago

Fri, Sep 19 - Sun, Sep 21

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$376 Roundtrip, found 3 hours ago

$376

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 21, priced at $376 found 3 hours ago

Fri, Sep 19 - Sun, Sep 21

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$383 Roundtrip, found 3 hours ago

$383

Roundtrip

found 3 hours ago

Select Delta flight, departing Fri, Sep 19 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 21, priced at $383 found 3 hours ago

Fri, Sep 19 - Sun, Sep 21

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$387 Roundtrip, found 3 hours ago

$387

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 21, priced at $387 found 3 hours ago

Fri, Sep 19 - Sun, Sep 21

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$394 Roundtrip, found 3 hours ago

$394

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 21, priced at $394 found 3 hours ago

Fri, Sep 19 - Sun, Sep 21

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$395 Roundtrip, found 3 hours ago

$395

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 21, priced at $395 found 3 hours ago

Fri, Sep 19 - Sun, Sep 21

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$397 Roundtrip, found 3 hours ago

$397

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 21, priced at $397 found 3 hours ago

Fri, Sep 19 - Sun, Sep 21

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$400 Roundtrip, found 3 hours ago

$400

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 21, priced at $400 found 3 hours ago

Fri, Sep 19 - Sun, Sep 21

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$400 Roundtrip, found 3 hours ago

$400

Roundtrip

found 3 hours ago

Select Delta flight, departing Fri, Sep 19 from O'Hare Intl. to Northwest Florida Regional, returning Sun, Sep 21, priced at $400 found 3 hours ago

Tue, Aug 19 - Mon, Aug 25

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$401 Roundtrip, found 3 hours ago

$401

Roundtrip

found 3 hours ago

Select Delta flight, departing Tue, Aug 19 from O'Hare Intl. to Northwest Florida Regional, returning Mon, Aug 25, priced at $401 found 3 hours ago