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Cheap flights from Pensacola to Chicago from $67

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 9/6. 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

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Find the cheapest flights from Pensacola to Chicago

Cheap round-trip flights

Southwest Logo
6:30 pm - 11:20 pmPNS-MDW
4h 50m1 stop
Southwest Logo
6:35 am - 1:15 pmMDW-PNS
6h 40m1 stop
$153Southwest
Find Deal
Tue, Aug 5 - Sat, Aug 9
Southwest Logo
11:20 am - 4:45 pmPNS-MDW
5h 25m2 stops
Southwest Logo
6:35 am - 1:15 pmMDW-PNS
6h 40m1 stop
$158Southwest
Find Deal
Tue, Aug 5 - Sat, Aug 9
Delta Logo
11:55 am - 5:47 pmPNS-MDW
5h 52m1 stop
Delta Logo
6:00 am - 10:50 amMDW-PNS
4h 50m1 stop
$177Delta
Find Deal
Wed, Aug 20 - Tue, Aug 26
Delta Logo
6:03 pm - 12:09 amPNS-ORD
6h 06m1 stop
Delta Logo
1:30 pm - 6:43 pmORD-PNS
5h 13m1 stop
$177Delta
Find Deal
Mon, Aug 4 - Wed, Aug 20
Spirit Airlines Logo
4:52 pm - 10:48 pmPNS-ORD
5h 56m1 stop
Spirit Airlines Logo
5:05 am - 3:39 pmORD-PNS
10h 34m1 stop
$181Spirit Airlines
Find Deal
Wed, Sep 24 - Wed, Oct 1
Spirit Airlines Logo
4:52 pm - 10:48 pmPNS-ORD
5h 56m1 stop
Spirit Airlines Logo
6:30 am - 5:00 pmORD-PNS
10h 30m1 stop
$182Spirit Airlines
Find Deal
Sun, Sep 7 - Fri, Sep 12
 Logo
8:46 am - 2:34 pmPNS-ORD
5h 48m1 stop
 Logo
7:20 am - 3:31 pmORD-PNS
8h 11m1 stop
Wed, Oct 15 - Sat, Nov 15
United Airlines Logo
2:15 pm - 4:52 pmPNS-ORD
2h 37mnonstop
United Airlines Logo
10:53 am - 1:18 pmORD-PNS
2h 25mnonstop
$223United Airlines
Find Deal
Wed, Aug 20 - Tue, Aug 26
 Logo
4:29 pm - 12:10 amPNS-ORD
7h 41m1 stop
 Logo
4:36 pm - 10:41 pmORD-PNS
6h 05m1 stop
Mon, Jul 28 - Wed, Jul 30
United Airlines Logo
2:08 pm - 4:47 pmPNS-ORD
2h 39mnonstop
United Airlines Logo
10:53 am - 1:18 pmORD-PNS
2h 25mnonstop
$232United Airlines
Find Deal
Mon, Aug 4 - Wed, Aug 27

Spirit Airlines flights from Pensacola to Chicago

Our best Spirit Airlines deals on Pensacola to Chicago flight tickets
Spirit Airlines
Sep 24
PNS4:52 pmPensacola
5h 56m
1 stop
ORD10:48 pmChicago O'Hare Intl
Oct 1
ORD5:05 amChicago O'Hare Intl
10h 34m
1 stop
PNS3:39 pmPensacola
Spirit Airlines
Sep 7
PNS4:52 pmPensacola
5h 56m
1 stop
ORD10:48 pmChicago O'Hare Intl
Sep 12
ORD6:30 amChicago O'Hare Intl
10h 30m
1 stop
PNS5:00 pmPensacola
Spirit Airlines
Jul 21
PNS6:00 amPensacola
11h 58m
1 stop
ORD5:58 pmChicago O'Hare Intl
Jul 23
ORD4:36 pmChicago O'Hare Intl
6h 05m
1 stop
PNS10:41 pmPensacola

United Airlines flights from Pensacola to Chicago

Our best United Airlines deals on Pensacola to Chicago flight tickets
United Airlines
Aug 20
PNS2:15 pmPensacola
2h 37m
ORD4:52 pmChicago O'Hare Intl
Aug 26
ORD10:53 amChicago O'Hare Intl
2h 25m
PNS1:18 pmPensacola
United Airlines
Aug 4
PNS2:08 pmPensacola
2h 39m
ORD4:47 pmChicago O'Hare Intl
Aug 27
ORD10:53 amChicago O'Hare Intl
2h 25m
PNS1:18 pmPensacola
United Airlines
Jul 18
PNS2:08 pmPensacola
2h 39m
ORD4:47 pmChicago O'Hare Intl
Jul 21
ORD10:39 amChicago O'Hare Intl
2h 27m
PNS1:06 pmPensacola

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 $279. If you’re not able to fly to Chicago in February, then July is your next best option. Flight prices from Pensacola to Chicago during July average around $279.

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 $406. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Pensacola to Chicago for around $691.

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 $518.

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 $343 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?

No. A direct flight is the cheapest option for a flight between Pensacola to Chicago.

How have Pensacola to Chicago flight prices changed over time?

As of July 2025, prices for Pensacola to Chicago flights are approximately 12% 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

$67

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Pensacola in the past 72 hours is $67. The best round-trip flight deal from Pensacola to Chicago found on momondo in the last 72 hours is $153.
The fastest flight from Pensacola to Chicago takes 2h 10m
Direct flights go from Pensacola to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Pensacola to Chicago by plane?

    A flight from Pensacola to Chicago will travel around 791.2 mi. 2h 10m 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 $152Free CancellationRating
6.3
8,063 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $192Free CancellationRating
8.0
4,256 reviews
Search Southwest flights
DeltaPriceFrom $194Free CancellationRating
8.0
7,958 reviews
Search Delta flights
American AirlinesPriceFrom $228Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $228Free CancellationRating
7.4
8,844 reviews
Search United Airlines flights
  • Southwest Flights From Pensacola to Chicago

    Southwest is one of the most popular airlines flying from Pensacola to Chicago, operating 5 flights/week on average for this route. A good Southwest flight deal for Pensacola to Chicago starts from $192 round-trip, up to an average price of $364. Our users have rated Southwest at 8.0/10.

  • United Airlines Flights From Pensacola to Chicago

    $228 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 $404, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 8,844 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
Portage
Saint Joseph
Lansing
Schererville
Valparaiso
Crown Point
Munster
Monticello
Chesterton
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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1 adult
Sun 7/13
Sun 7/20

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