Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Pensacola to Chicago from $80

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Pensacola to Chicago departing on 1/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Pensacola to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:33 pm - 10:41 am
PNS
-
ORD
17h 08m1 stop
Multiple Airlines Logo
6:05 am - 4:37 pm
ORD
-
PNS
10h 32m1 stop
$154Multiple Airlines
Wed, Jan 21 - Tue, Jan 27
Multiple Airlines Logo
5:33 pm - 10:41 am
PNS
-
ORD
17h 08m1 stop
Multiple Airlines Logo
10:48 am - 4:37 pm
ORD
-
PNS
5h 49m1 stop
$161Multiple Airlines
Wed, Jan 21 - Wed, Jan 28
Spirit Airlines Logo
4:03 pm - 11:22 am
PNS
-
ORD
19h 19m1 stop
Spirit Airlines Logo
10:48 am - 4:37 pm
ORD
-
PNS
5h 49m1 stop
$162Spirit Airlines
Fri, Jan 23 - Tue, Jan 27
Multiple Airlines Logo
5:33 pm - 2:39 pm
PNS
-
ORD
21h 06m1 stop
Multiple Airlines Logo
12:44 pm - 4:37 pm
ORD
-
PNS
27h 53m1 stop
$164Multiple Airlines
Fri, Jan 16 - Mon, Jan 19
Spirit Airlines Logo
5:33 pm - 1:13 pm
PNS
-
ORD
19h 40m1 stop
Spirit Airlines Logo
10:48 am - 4:37 pm
ORD
-
PNS
5h 49m1 stop
$168Spirit Airlines
Tue, Jan 20 - Sat, Jan 31
Multiple Airlines Logo
5:33 pm - 10:41 am
PNS
-
ORD
17h 08m1 stop
Multiple Airlines Logo
10:48 am - 4:37 pm
ORD
-
PNS
5h 49m1 stop
$169Multiple Airlines
Wed, Jan 21 - Mon, Jan 26
Spirit Airlines Logo
4:03 pm - 11:22 am
PNS
-
ORD
19h 19m1 stop
Spirit Airlines Logo
12:44 pm - 4:37 pm
ORD
-
PNS
27h 53m1 stop
$171Spirit Airlines
Mon, Jan 12 - Sun, Jan 18
Southwest Logo
4:00 pm - 10:05 pm
PNS
-
MDW
6h 05m1 stop
Southwest Logo
5:25 am - 9:25 am
MDW
-
PNS
4h 00m1 stop
$229Southwest
Wed, Jan 14 - Thu, Jan 15
Southwest Logo
7:50 am - 1:25 pm
PNS
-
MDW
5h 35m1 stop
Southwest Logo
6:15 am - 3:15 pm
MDW
-
PNS
9h 00m2 stops
$234Southwest
Wed, Jan 21 - Wed, Jan 28
Delta Logo
5:54 pm - 10:07 pm
PNS
-
MDW
4h 13m1 stop
Delta Logo
6:00 am - 10:26 am
MDW
-
PNS
4h 26m1 stop
$274Delta
Fri, Jan 16 - Mon, Jan 19

Delta flights from Pensacola to Chicago

Our best Delta deals on Pensacola to Chicago flight tickets
Delta
Jan 18
PNS6:00 amPensacola
4h 07m
1 stop
ORD10:07 amChicago O'Hare Intl
Jan 27
ORD5:59 pmChicago O'Hare Intl
5h 14m
1 stop
PNS11:13 pmPensacola
$229
Find similar
Delta
Jan 16
PNS5:54 pmPensacola
4h 13m
1 stop
MDW10:07 pmChicago Midway
Jan 19
MDW10:46 amChicago Midway
4h 08m
1 stop
PNS2:54 pmPensacola
$274
Find similar
Delta
Mar 14
PNS10:54 amPensacola
4h 31m
1 stop
MDW3:25 pmChicago Midway
Mar 18
MDW10:45 amChicago Midway
4h 24m
1 stop
PNS3:09 pmPensacola
$284
Find similar

Spirit Airlines flights from Pensacola to Chicago

Our best Spirit Airlines deals on Pensacola to Chicago flight tickets
Spirit Airlines
Jan 23
PNS4:03 pmPensacola
19h 19m
1 stop
ORD11:22 amChicago O'Hare Intl
Jan 27
ORD10:48 amChicago O'Hare Intl
5h 49m
1 stop
PNS4:37 pmPensacola
$162
Find similar
Spirit Airlines
Jan 20
PNS5:33 pmPensacola
19h 40m
1 stop
ORD1:13 pmChicago O'Hare Intl
Jan 31
ORD10:48 amChicago O'Hare Intl
5h 49m
1 stop
PNS4:37 pmPensacola
$168
Find similar
Spirit Airlines
Jan 12
PNS4:03 pmPensacola
19h 19m
1 stop
ORD11:22 amChicago O'Hare Intl
Jan 18
ORD12:44 pmChicago O'Hare Intl
27h 53m
1 stop
PNS4:37 pmPensacola
$171
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Pensacola to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 23, 2025.
Use the filters below to find and compare flights from Pensacola to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 1/21

5:33 pm-10:41 am

1 stop17h 08m

Chicago O'Hare Intl

Tue 1/27

6:05 am-4:37 pm

1 stop10h 32m

$154

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 1/21

5:33 pm-10:41 am

1 stop17h 08m

Chicago O'Hare Intl

Wed 1/28

10:48 am-4:37 pm

1 stop5h 49m

$161

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 1/23

4:03 pm-11:22 am

1 stop19h 19m

Chicago O'Hare Intl

Tue 1/27

10:48 am-4:37 pm

1 stop5h 49m

$162

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 1/16

5:33 pm-2:39 pm

1 stop21h 06m

Chicago O'Hare Intl

Mon 1/19

12:44 pm-4:37 pm

1 stop27h 53m

$164

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 1/20

5:33 pm-1:13 pm

1 stop19h 40m

Chicago O'Hare Intl

Sat 1/31

10:48 am-4:37 pm

1 stop5h 49m

$168

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 1/21

5:33 pm-10:41 am

1 stop17h 08m

Chicago O'Hare Intl

Mon 1/26

10:48 am-4:37 pm

1 stop5h 49m

$169

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Mon 1/12

4:03 pm-11:22 am

1 stop19h 19m

Chicago O'Hare Intl

Sun 1/18

12:44 pm-4:37 pm

1 stop27h 53m

$171

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 1/14

4:00 pm-10:05 pm

1 stop6h 05m

Chicago Midway

Thu 1/15

5:25 am-9:25 am

1 stop4h 00m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 1/21

7:50 am-1:25 pm

1 stop5h 35m

Chicago Midway

Wed 1/28

6:15 am-3:15 pm

2 stops9h 00m

$234

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 1/16

5:54 pm-10:07 pm

1 stop4h 13m

Chicago Midway

Mon 1/19

6:00 am-10:26 am

1 stop4h 26m

$274

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Pensacola to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Pensacola, with most prices found around $254. If you’re not able to fly to Chicago in February, then November is your next best option. Flight prices from Pensacola to Chicago during November average around $273.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $368. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Pensacola to Chicago for around $558.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Pensacola to Chicago during this time can be as low as $307. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $430.

What is the cheapest Pensacola to Chicago flight route?

Fly from Pensacola to Chicago O'Hare Intl for the best Pensacola - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Pensacola when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $306 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Pensacola for as low as $196 on momondo.

What cabin class options are available on Pensacola to Chicago flights?

There are 4 cabin classes available to choose from on Pensacola to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Pensacola to Chicago flights?

You could potentially save up to 9% on your flight if you consider stops on a Pensacola to Chicago flight.

How have Pensacola to Chicago flight prices changed over time?

As of December 2025, prices for Pensacola to Chicago flights are approximately 148% more expensive when compared to flights at the same time last year.

When to book flights from Pensacola to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Pensacola to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Pensacola to Chicago (PNS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Pensacola to Chicago

Best Price Found

$219

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Pensacola in the past 72 hours is $219. The best round-trip flight deal from Pensacola to Chicago found on momondo in the last 72 hours is $299.
The fastest flight from Pensacola to Chicago takes 2h 15m
Direct flights go from Pensacola to Chicago every day.
There are 3 airports in Chicago. From Pensacola there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

  • How far is Pensacola to Chicago by plane?

    A flight from Pensacola to Chicago will travel around 791.2 mi. 2h 15m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Pensacola Airport to Chicago?

    Prices for flights from Pensacola Airport to Chicago were last updated today.

  • How many operators does momondo search for flights from Pensacola Airport to Chicago?

  • How old do you have to be to fly from Pensacola Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Pensacola Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Pensacola to Chicago?

  • What is the most popular airline from Pensacola to Chicago?

Best airlines flying from Pensacola to Chicago

Compare and see reviews for airlines that fly from Pensacola to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $155Free CancellationRating
6.3
8,196 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $173Free CancellationRating
8.0
4,253 reviews
Search Southwest flights
DeltaPriceFrom $196Free CancellationRating
7.9
8,014 reviews
Search Delta flights
United AirlinesPriceFrom $209Free CancellationRating
7.4
9,105 reviews
Search United Airlines flights
American AirlinesPriceFrom $238Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights

  • Southwest Flights From Pensacola to Chicago

    Southwest is one of the most popular airlines flying from Pensacola to Chicago, operating 4 flights/week on average for this route. A good Southwest flight deal for Pensacola to Chicago starts from $173 round-trip, up to an average price of $315. Our users have rated Southwest at 8.0/10.

  • United Airlines Flights From Pensacola to Chicago

    $209 is the best United Airlines flight deal from Pensacola to Chicago found on momondo over the last 72 hours. The average United Airlines ticket price found was closer to $313, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 9,105 user reviews) flies into Chicago from Pensacola 7 times in an average week so prices can vary.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Pensacola to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Pensacola.

Can I find flights from Pensacola to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Pensacola which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Pensacola to Chicago?

momondo helps you find the best flight between Pensacola and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Pensacola to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Pensacola to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 1/22
Thu 1/29
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport