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.

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$237 Roundtrip, found 4 days ago

$237

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $237 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$256 Roundtrip, found 4 days ago

$256

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $256 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$272 Roundtrip, found 4 days ago

$272

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $272 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$278 Roundtrip, found 4 days ago

$278

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $278 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$281 Roundtrip, found 4 days ago

$281

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $281 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$285 Roundtrip, found 4 days ago

$285

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $285 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$288 Roundtrip, found 4 days ago

$288

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $288 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$289 Roundtrip, found 4 days ago

$289

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $289 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$290 Roundtrip, found 4 days ago

$290

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $290 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$307 Roundtrip, found 4 days ago

$307

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $307 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$307 Roundtrip, found 4 days ago

$307

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $307 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$310 Roundtrip, found 4 days ago

$310

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $310 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$311 Roundtrip, found 4 days ago

$311

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $311 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$314 Roundtrip, found 4 days ago

$314

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $314 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$315 Roundtrip, found 4 days ago

$315

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $315 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$316 Roundtrip, found 4 days ago

$316

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $316 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$321 Roundtrip, found 4 days ago

$321

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $321 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$323 Roundtrip, found 4 days ago

$323

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $323 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$332 Roundtrip, found 4 days ago

$332

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $332 found 4 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

ECP

Northwest Florida Beaches Intl.

$339 Roundtrip, found 4 days ago

$339

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Nov 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Tue, Nov 11, priced at $339 found 4 days ago