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Cheap flights from Pensacola to Chicago from $69

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 5/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Pensacola to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
5:20 pm - 11:47 pm
PNS
-
ORD
6h 27m
1 stop
Spirit Airlines Logo
10:44 am - 5:42 pm
ORD
-
PNS
6h 58m
1 stop
$151Spirit Airlines
Wed, Mar 4 - Sat, Mar 7
Multiple Airlines Logo
6:37 pm - 3:52 pm
PNS
-
ORD
21h 15m
1 stop
Multiple Airlines Logo
8:30 am - 5:42 pm
ORD
-
PNS
9h 12m
1 stop
$155Multiple Airlines
Tue, Feb 24 - Tue, Mar 3
Spirit Airlines Logo
5:20 pm - 11:47 pm
PNS
-
ORD
6h 27m
1 stop
Spirit Airlines Logo
12:44 pm - 5:42 pm
ORD
-
PNS
4h 58m
1 stop
$157Spirit Airlines
Sat, Feb 14 - Wed, Feb 18
Multiple Airlines Logo
6:37 pm - 11:38 pm
PNS
-
ORD
29h 01m
1 stop
Multiple Airlines Logo
4:18 pm - 5:42 pm
ORD
-
PNS
25h 24m
1 stop
$162Multiple Airlines
Fri, Mar 6 - Mon, Mar 9
Spirit Airlines Logo
5:20 pm - 11:47 pm
PNS
-
ORD
6h 27m
1 stop
Spirit Airlines Logo
7:00 am - 3:54 pm
ORD
-
PNS
8h 54m
1 stop
$167Spirit Airlines
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
6:37 pm - 11:22 am
PNS
-
ORD
16h 45m
2 stops
Multiple Airlines Logo
8:30 am - 5:42 pm
ORD
-
PNS
9h 12m
1 stop
$169Multiple Airlines
Tue, Feb 24 - Tue, Mar 3
Multiple Airlines Logo
6:37 pm - 11:38 pm
PNS
-
ORD
29h 01m
1 stop
Multiple Airlines Logo
8:16 pm - 5:42 pm
ORD
-
PNS
21h 26m
2 stops
$170Multiple Airlines
Fri, Mar 6 - Mon, Mar 9
Spirit Airlines Logo
5:20 pm - 11:47 pm
PNS
-
ORD
6h 27m
1 stop
Spirit Airlines Logo
12:44 pm - 10:27 pm
ORD
-
PNS
9h 43m
1 stop
$172Spirit Airlines
Wed, Mar 4 - Wed, Mar 11
Delta Logo
5:48 pm - 10:31 pm
PNS
-
MDW
4h 43m
1 stop
Delta Logo
10:45 am - 3:09 pm
MDW
-
PNS
4h 24m
1 stop
$227Delta
Thu, Mar 5 - Tue, Mar 10
Southwest Logo
4:00 pm - 10:05 pm
PNS
-
MDW
6h 05m
1 stop
Southwest Logo
9:00 am - 11:15 am
MDW
-
PNS
2h 15mnonstop
$237Southwest
Wed, Mar 4 - Sat, Mar 7

United Airlines flights from Pensacola to Chicago

Our best United Airlines deals on Pensacola to Chicago flight tickets
United Airlines
Mar 5
PNS2:18 pmPensacola
2h 39m
ORD4:57 pmChicago O'Hare Intl
Mar 6
ORD6:05 pmChicago O'Hare Intl
2h 25m
PNS8:30 pmPensacola
$207
United Airlines
Feb 19
PNS4:08 pmPensacola
2h 47m
ORD6:55 pmChicago O'Hare Intl
Feb 23
ORD10:40 amChicago O'Hare Intl
2h 27m
PNS1:07 pmPensacola
$227
United Airlines
Feb 14
PNS4:08 pmPensacola
2h 47m
ORD6:55 pmChicago O'Hare Intl
Feb 16
ORD12:50 pmChicago O'Hare Intl
2h 37m
PNS3:27 pmPensacola
$253

Spirit Airlines flights from Pensacola to Chicago

Our best Spirit Airlines deals on Pensacola to Chicago flight tickets
Spirit Airlines
Mar 4
PNS5:20 pmPensacola
6h 27m
1 stop
ORD11:47 pmChicago O'Hare Intl
Mar 11
ORD5:15 amChicago O'Hare Intl
10h 39m
1 stop
PNS3:54 pmPensacola
$148
Spirit Airlines
Mar 4
PNS5:20 pmPensacola
6h 27m
1 stop
ORD11:47 pmChicago O'Hare Intl
Mar 7
ORD10:44 amChicago O'Hare Intl
6h 58m
1 stop
PNS5:42 pmPensacola
$151
Spirit Airlines
Mar 4
PNS5:20 pmPensacola
6h 27m
1 stop
ORD11:47 pmChicago O'Hare Intl
Mar 11
ORD5:15 amChicago O'Hare Intl
12h 27m
2 stops
PNS5:42 pmPensacola
$165

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 February 4, 2026.
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 3/4

5:20 pm-11:47 pm

1 stop6h 27m

Chicago O'Hare Intl

Sat 3/7

10:44 am-5:42 pm

1 stop6h 58m

$151

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 2/24

6:37 pm-3:52 pm

1 stop21h 15m

Chicago O'Hare Intl

Tue 3/3

8:30 am-5:42 pm

1 stop9h 12m

$155

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sat 2/14

5:20 pm-11:47 pm

1 stop6h 27m

Chicago O'Hare Intl

Wed 2/18

12:44 pm-5:42 pm

1 stop4h 58m

$157

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 3/6

6:37 pm-11:38 pm

1 stop29h 01m

Chicago O'Hare Intl

Mon 3/9

4:18 pm-5:42 pm

1 stop25h 24m

$162

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 3/5

5:20 pm-11:47 pm

1 stop6h 27m

Chicago O'Hare Intl

Mon 3/9

7:00 am-3:54 pm

1 stop8h 54m

$167

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 2/24

6:37 pm-11:22 am

2 stops16h 45m

Chicago O'Hare Intl

Tue 3/3

8:30 am-5:42 pm

1 stop9h 12m

$169

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 3/6

6:37 pm-11:38 pm

1 stop29h 01m

Chicago O'Hare Intl

Mon 3/9

8:16 pm-5:42 pm

2 stops21h 26m

$170

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 3/4

5:20 pm-11:47 pm

1 stop6h 27m

Chicago O'Hare Intl

Wed 3/11

12:44 pm-10:27 pm

1 stop9h 43m

$172

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 3/5

5:48 pm-10:31 pm

1 stop4h 43m

Chicago Midway

Tue 3/10

10:45 am-3:09 pm

1 stop4h 24m

$227

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 3/4

4:00 pm-10:05 pm

1 stop6h 05m

Chicago Midway

Sat 3/7

9:00 am-11:15 am

Nonstop2h 15m

$237

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Pensacola and Chicago?

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 $379. 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 $534.

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 morning. Flights from Pensacola to Chicago during this time can be as low as $401. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $429.

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 $310 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 February 2026, prices for Pensacola to Chicago flights are approximately 31% cheaper 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

$183

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 $183. The best round-trip flight deal from Pensacola to Chicago found on momondo in the last 72 hours is $279.
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
8,411 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $173Free CancellationRating
8.0
4,274 reviews
Search Southwest flights
DeltaPriceFrom $196Free CancellationRating
7.9
8,145 reviews
Search Delta flights
United AirlinesPriceFrom $209Free CancellationRating
7.4
9,236 reviews
Search United Airlines flights
American AirlinesPriceFrom $209Free CancellationRating
7.2
11,222 reviews
Search American Airlines flights

  • United Airlines Flights From Pensacola to Chicago

    United Airlines is one of the most popular airlines flying from Pensacola to Chicago, operating 12 flights/week on average for this route. A good United Airlines flight deal for Pensacola to Chicago starts from $209 round-trip, up to an average price of $325. Our users have rated United Airlines at 7.4/10.

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
Schererville
Valparaiso
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.

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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