Flights from Chicago to Fort Walton Beach - Destin

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, Sep 23 - Wed, Sep 24

MDW

Midway Intl.

PNS

Pensacola Intl.

$237 Roundtrip, found 4 days ago

$237

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Sep 23 from Midway Intl. to Pensacola Intl., returning Wed, Sep 24, priced at $237 found 4 days ago

Tue, Sep 23 - Sun, Sep 28

MDW

Midway Intl.

PNS

Pensacola Intl.

$244 Roundtrip, found 4 days ago

$244

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Sep 23 from Midway Intl. to Pensacola Intl., returning Sun, Sep 28, priced at $244 found 4 days ago

Mon, Sep 22 - Fri, Sep 26

MDW

Midway Intl.

PNS

Pensacola Intl.

$265 Roundtrip, found 4 days ago

$265

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Sep 22 from Midway Intl. to Pensacola Intl., returning Fri, Sep 26, priced at $265 found 4 days ago

Wed, Dec 17 - Thu, Dec 25

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$267 Roundtrip, found 18 hours ago

$267

Roundtrip

found 18 hours ago

Select Delta flight, departing Wed, Dec 17 from O'Hare Intl. to Pensacola Intl., returning Thu, Dec 25, priced at $267 found 18 hours ago

Fri, Sep 19 - Tue, Sep 23

MDW

Midway Intl.

PNS

Pensacola Intl.

$268 Roundtrip, found 4 days ago

$268

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Sep 19 from Midway Intl. to Pensacola Intl., returning Tue, Sep 23, priced at $268 found 4 days ago

Fri, Sep 19 - Sun, Sep 28

MDW

Midway Intl.

PNS

Pensacola Intl.

$275 Roundtrip, found 4 days ago

$275

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Sep 19 from Midway Intl. to Pensacola Intl., returning Sun, Sep 28, priced at $275 found 4 days ago

Thu, Sep 25 - Sat, Sep 27

MDW

Midway Intl.

PNS

Pensacola Intl.

$288 Roundtrip, found 4 days ago

$288

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Sep 25 from Midway Intl. to Pensacola Intl., returning Sat, Sep 27, priced at $288 found 4 days ago

Mon, Sep 22 - Fri, Sep 26

MDW

Midway Intl.

PNS

Pensacola Intl.

$295 Roundtrip, found 4 days ago

$295

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Sep 22 from Midway Intl. to Pensacola Intl., returning Fri, Sep 26, priced at $295 found 4 days ago

Mon, Dec 22 - Thu, Dec 25

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$318 Roundtrip, found 18 hours ago

$318

Roundtrip

found 18 hours ago

Select Delta flight, departing Mon, Dec 22 from O'Hare Intl. to Pensacola Intl., returning Thu, Dec 25, priced at $318 found 18 hours ago

Mon, Sep 22 - Fri, Sep 26

MDW

Midway Intl.

PNS

Pensacola Intl.

$319 Roundtrip, found 4 days ago

$319

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Sep 22 from Midway Intl. to Pensacola Intl., returning Fri, Sep 26, priced at $319 found 4 days ago

Sun, Sep 21 - Tue, Sep 23

MDW

Midway Intl.

PNS

Pensacola Intl.

$332 Roundtrip, found 4 days ago

$332

Roundtrip

found 4 days ago

Select Delta flight, departing Sun, Sep 21 from Midway Intl. to Pensacola Intl., returning Tue, Sep 23, priced at $332 found 4 days ago

Tue, Oct 21 - Sat, Oct 25

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$334 Roundtrip, found 6 days ago

$334

Roundtrip

found 6 days ago

Select American Airlines flight, departing Tue, Oct 21 from O'Hare Intl. to Northwest Florida Regional, returning Sat, Oct 25, priced at $334 found 6 days ago

Mon, Sep 22 - Fri, Sep 26

MDW

Midway Intl.

PNS

Pensacola Intl.

$335 Roundtrip, found 4 days ago

$335

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Sep 22 from Midway Intl. to Pensacola Intl., returning Fri, Sep 26, priced at $335 found 4 days ago

Sun, Sep 21 - Sun, Sep 28

MDW

Midway Intl.

PNS

Pensacola Intl.

$339 Roundtrip, found 4 days ago

$339

Roundtrip

found 4 days ago

Select Delta flight, departing Sun, Sep 21 from Midway Intl. to Pensacola Intl., returning Sun, Sep 28, priced at $339 found 4 days ago

Mon, Sep 22 - Fri, Sep 26

MDW

Midway Intl.

PNS

Pensacola Intl.

$345 Roundtrip, found 4 days ago

$345

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Sep 22 from Midway Intl. to Pensacola Intl., returning Fri, Sep 26, priced at $345 found 4 days ago

Thu, Dec 18 - Sat, Dec 27

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$347 Roundtrip, found 18 hours ago

$347

Roundtrip

found 18 hours ago

Select United flight, departing Thu, Dec 18 from O'Hare Intl. to Pensacola Intl., returning Sat, Dec 27, priced at $347 found 18 hours ago

Tue, Oct 21 - Sat, Oct 25

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$352 Roundtrip, found 6 days ago

$352

Roundtrip

found 6 days ago

Select American Airlines flight, departing Tue, Oct 21 from O'Hare Intl. to Northwest Florida Regional, returning Sat, Oct 25, priced at $352 found 6 days ago

Tue, Oct 21 - Sat, Oct 25

ORD

O'Hare Intl.

VPS

Northwest Florida Regional

$360 Roundtrip, found 6 days ago

$360

Roundtrip

found 6 days ago

Select American Airlines flight, departing Tue, Oct 21 from O'Hare Intl. to Northwest Florida Regional, returning Sat, Oct 25, priced at $360 found 6 days ago

Wed, Dec 17 - Sun, Dec 28

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$364 Roundtrip, found 18 hours ago

$364

Roundtrip

found 18 hours ago

Select Spirit Airlines flight, departing Wed, Dec 17 from O'Hare Intl. to Pensacola Intl., returning Sun, Dec 28, priced at $364 found 18 hours ago

Mon, Sep 22 - Fri, Sep 26

MDW

Midway Intl.

PNS

Pensacola Intl.

$365 Roundtrip, found 4 days ago

$365

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Sep 22 from Midway Intl. to Pensacola Intl., returning Fri, Sep 26, priced at $365 found 4 days ago