Flights from Chicago to Southern Alabama

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.

Sat, Sep 13 - Tue, Sep 16

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$157 Roundtrip, found 5 hours ago

$157

Roundtrip

found 5 hours ago

Select Delta flight, departing Sat, Sep 13 from O'Hare Intl. to Pensacola Intl., returning Tue, Sep 16, priced at $157 found 5 hours ago

Sat, Sep 13 - Tue, Sep 16

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$161 Roundtrip, found 5 hours ago

$161

Roundtrip

found 5 hours ago

Select Spirit Airlines flight, departing Sat, Sep 13 from O'Hare Intl. to Pensacola Intl., returning Tue, Sep 16, priced at $161 found 5 hours ago

Sat, Sep 13 - Tue, Sep 16

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$165 Roundtrip, found 5 hours ago

$165

Roundtrip

found 5 hours ago

Select United flight, departing Sat, Sep 13 from O'Hare Intl. to Pensacola Intl., returning Tue, Sep 16, priced at $165 found 5 hours ago

Sat, Sep 13 - Tue, Sep 16

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$177 Roundtrip, found 5 hours ago

$177

Roundtrip

found 5 hours ago

Select Delta flight, departing Sat, Sep 13 from O'Hare Intl. to Pensacola Intl., returning Tue, Sep 16, priced at $177 found 5 hours ago

Sat, Sep 13 - Tue, Sep 16

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$183 Roundtrip, found 5 hours ago

$183

Roundtrip

found 5 hours ago

Select Frontier Airlines flight, departing Sat, Sep 13 from O'Hare Intl. to Pensacola Intl., returning Tue, Sep 16, priced at $183 found 5 hours ago

Sat, Sep 13 - Tue, Sep 16

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$184 Roundtrip, found 5 hours ago

$184

Roundtrip

found 5 hours ago

Select Spirit Airlines flight, departing Sat, Sep 13 from O'Hare Intl. to Pensacola Intl., returning Tue, Sep 16, priced at $184 found 5 hours ago

Tue, Sep 9 - Fri, Sep 12

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$185 Roundtrip, found 11 hours ago

$185

Roundtrip

found 11 hours ago

Select Delta flight, departing Tue, Sep 9 from O'Hare Intl. to Pensacola Intl., returning Fri, Sep 12, priced at $185 found 11 hours ago

Thu, Sep 11 - Mon, Sep 15

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$188 Roundtrip, found 11 hours ago

$188

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Thu, Sep 11 from O'Hare Intl. to Pensacola Intl., returning Mon, Sep 15, priced at $188 found 11 hours ago

Sat, Sep 13 - Tue, Sep 16

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$192 Roundtrip, found 5 hours ago

$192

Roundtrip

found 5 hours ago

Select Delta flight, departing Sat, Sep 13 from O'Hare Intl. to Pensacola Intl., returning Tue, Sep 16, priced at $192 found 5 hours ago

Wed, Sep 10 - Sun, Sep 14

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$204 Roundtrip, found 11 hours ago

$204

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Wed, Sep 10 from O'Hare Intl. to Pensacola Intl., returning Sun, Sep 14, priced at $204 found 11 hours ago

Sat, Sep 13 - Tue, Sep 16

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$207 Roundtrip, found 5 hours ago

$207

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Sat, Sep 13 from O'Hare Intl. to Pensacola Intl., returning Tue, Sep 16, priced at $207 found 5 hours ago

Mon, Sep 15 - Mon, Sep 15

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$211 Roundtrip, found 11 hours ago

$211

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Mon, Sep 15 from O'Hare Intl. to Pensacola Intl., returning Mon, Sep 15, priced at $211 found 11 hours ago

Tue, Sep 23 - Sat, Sep 27

ORD

O'Hare Intl.

MOB

Mobile Regional

$211 Roundtrip, found 1 day ago

$211

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Sep 23 from O'Hare Intl. to Mobile Regional, returning Sat, Sep 27, priced at $211 found 1 day ago

Sat, Sep 13 - Tue, Sep 16

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$213 Roundtrip, found 5 hours ago

$213

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Sat, Sep 13 from O'Hare Intl. to Pensacola Intl., returning Tue, Sep 16, priced at $213 found 5 hours ago

Sat, Sep 13 - Tue, Sep 16

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$218 Roundtrip, found 5 hours ago

$218

Roundtrip

found 5 hours ago

Select Delta flight, departing Sat, Sep 13 from O'Hare Intl. to Pensacola Intl., returning Tue, Sep 16, priced at $218 found 5 hours ago

Sat, Sep 13 - Tue, Sep 16

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$220 Roundtrip, found 5 hours ago

$220

Roundtrip

found 5 hours ago

Select United flight, departing Sat, Sep 13 from O'Hare Intl. to Pensacola Intl., returning Tue, Sep 16, priced at $220 found 5 hours ago

Fri, Sep 12 - Fri, Sep 12

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$221 Roundtrip, found 11 hours ago

$221

Roundtrip

found 11 hours ago

Select Spirit Airlines flight, departing Fri, Sep 12 from O'Hare Intl. to Pensacola Intl., returning Fri, Sep 12, priced at $221 found 11 hours ago

Sat, Sep 13 - Tue, Sep 16

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$221 Roundtrip, found 5 hours ago

$221

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Sat, Sep 13 from O'Hare Intl. to Pensacola Intl., returning Tue, Sep 16, priced at $221 found 5 hours ago

Sat, Sep 13 - Tue, Sep 16

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$222 Roundtrip, found 5 hours ago

$222

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Sat, Sep 13 from O'Hare Intl. to Pensacola Intl., returning Tue, Sep 16, priced at $222 found 5 hours ago

Sat, Sep 20 - Wed, Oct 1

ORD

O'Hare Intl.

MOB

Mobile Regional

$281 Roundtrip, found 1 day ago

$281

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sat, Sep 20 from O'Hare Intl. to Mobile Regional, returning Wed, Oct 1, priced at $281 found 1 day ago