Flights from Pensacola to Chicago

Cheapest flights from Pensacola

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 - Mon, Sep 22

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$167 Roundtrip, found 2 days ago

$167

Roundtrip

found 2 days ago

Select United flight, departing Thu, Sep 18 from Pensacola Intl. to O'Hare Intl., returning Mon, Sep 22, priced at $167 found 2 days ago

Tue, Sep 23 - Tue, Sep 30

PNS

Pensacola Intl.

MDW

Midway Intl.

$177 Roundtrip, found 5 days ago

$177

Roundtrip

found 5 days ago

Select Delta flight, departing Tue, Sep 23 from Pensacola Intl. to Midway Intl., returning Tue, Sep 30, priced at $177 found 5 days ago

Fri, Sep 19 - Mon, Sep 22

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$180 Roundtrip, found 2 days ago

$180

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Fri, Sep 19 from Pensacola Intl. to O'Hare Intl., returning Mon, Sep 22, priced at $180 found 2 days ago

Thu, Sep 25 - Tue, Sep 30

PNS

Pensacola Intl.

MDW

Midway Intl.

$191 Roundtrip, found 5 days ago

$191

Roundtrip

found 5 days ago

Select Delta flight, departing Thu, Sep 25 from Pensacola Intl. to Midway Intl., returning Tue, Sep 30, priced at $191 found 5 days ago

Fri, Sep 26 - Mon, Sep 29

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$195 Roundtrip, found 5 days ago

$195

Roundtrip

found 5 days ago

Select United flight, departing Fri, Sep 26 from Pensacola Intl. to O'Hare Intl., returning Mon, Sep 29, priced at $195 found 5 days ago

Thu, Sep 18 - Mon, Sep 22

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$202 Roundtrip, found 2 days ago

$202

Roundtrip

found 2 days ago

Select United flight, departing Thu, Sep 18 from Pensacola Intl. to O'Hare Intl., returning Mon, Sep 22, priced at $202 found 2 days ago

Fri, Sep 26 - Mon, Sep 29

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$204 Roundtrip, found 5 days ago

$204

Roundtrip

found 5 days ago

Select United flight, departing Fri, Sep 26 from Pensacola Intl. to O'Hare Intl., returning Mon, Sep 29, priced at $204 found 5 days ago

Fri, Sep 19 - Sun, Sep 21

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$204 Roundtrip, found 2 days ago

$204

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Fri, Sep 19 from Pensacola Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $204 found 2 days ago

Fri, Sep 26 - Mon, Sep 29

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$205 Roundtrip, found 5 days ago

$205

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Fri, Sep 26 from Pensacola Intl. to O'Hare Intl., returning Mon, Sep 29, priced at $205 found 5 days ago

Fri, Sep 26 - Mon, Sep 29

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$209 Roundtrip, found 5 days ago

$209

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Fri, Sep 26 from Pensacola Intl. to O'Hare Intl., returning Mon, Sep 29, priced at $209 found 5 days ago

Fri, Sep 26 - Mon, Sep 29

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$213 Roundtrip, found 5 days ago

$213

Roundtrip

found 5 days ago

Select United flight, departing Fri, Sep 26 from Pensacola Intl. to O'Hare Intl., returning Mon, Sep 29, priced at $213 found 5 days ago

Tue, Sep 23 - Fri, Sep 26

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$215 Roundtrip, found 5 days ago

$215

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Tue, Sep 23 from Pensacola Intl. to O'Hare Intl., returning Fri, Sep 26, priced at $215 found 5 days ago

Fri, Sep 19 - Sun, Sep 21

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$219 Roundtrip, found 2 days ago

$219

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Fri, Sep 19 from Pensacola Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $219 found 2 days ago

Fri, Sep 26 - Mon, Sep 29

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$223 Roundtrip, found 5 days ago

$223

Roundtrip

found 5 days ago

Select United flight, departing Fri, Sep 26 from Pensacola Intl. to O'Hare Intl., returning Mon, Sep 29, priced at $223 found 5 days ago

Fri, Sep 26 - Mon, Sep 29

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$224 Roundtrip, found 5 days ago

$224

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Fri, Sep 26 from Pensacola Intl. to O'Hare Intl., returning Mon, Sep 29, priced at $224 found 5 days ago

Fri, Sep 26 - Thu, Oct 2

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$225 Roundtrip, found 5 days ago

$225

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Fri, Sep 26 from Pensacola Intl. to O'Hare Intl., returning Thu, Oct 2, priced at $225 found 5 days ago

Thu, Sep 25 - Fri, Sep 26

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$230 Roundtrip, found 5 days ago

$230

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Thu, Sep 25 from Pensacola Intl. to O'Hare Intl., returning Fri, Sep 26, priced at $230 found 5 days ago

Fri, Sep 26 - Mon, Sep 29

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$230 Roundtrip, found 5 days ago

$230

Roundtrip

found 5 days ago

Select United flight, departing Fri, Sep 26 from Pensacola Intl. to O'Hare Intl., returning Mon, Sep 29, priced at $230 found 5 days ago

Thu, Sep 18 - Mon, Sep 22

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$234 Roundtrip, found 2 days ago

$234

Roundtrip

found 2 days ago

Select American Airlines flight, departing Thu, Sep 18 from Pensacola Intl. to O'Hare Intl., returning Mon, Sep 22, priced at $234 found 2 days ago

Thu, Sep 18 - Mon, Sep 22

PNS

Pensacola Intl.

ORD

O'Hare Intl.

$251 Roundtrip, found 2 days ago

$251

Roundtrip

found 2 days ago

Select American Airlines flight, departing Thu, Sep 18 from Pensacola Intl. to O'Hare Intl., returning Mon, Sep 22, priced at $251 found 2 days ago