What is the cheapest airline that flies from Chicago to Pensacola?

American Airlines, United Airlines, and Southwest are the most popular carriers operating from Chicago to Pensacola

How many flights depart from Chicago to Pensacola on average per week?

As of July 2025, there are 18 flights per week flying from Chicago to Pensacola. The most common day of the week flights depart is Mon, with 22% of flights taking off on this day.

How many flights depart from Chicago to Pensacola on average per day?

The number of flights available between Chicago and Pensacola is 2 per day as of July 2025. The most frequent departure time is 10:00AM, with 100% of daily flights leaving at noon.

What airlines fly to Pensacola?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Pensacola from Chicago according to our data. United Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Pensacola. Keep in mind that there are 6 different airlines that fly to Pensacola on a routine basis, so you have a few additional options to choose from.

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

Prices for flights from Chicago to Pensacola Airport refresh daily.

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

As of July 2025, there are 5 operators available to choose from for flights from Chicago to Pensacola Airport.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Pensacola Airport.

What documentation or ID do you need to fly to Pensacola Airport?

The travel and health documents required for your trip to Pensacola Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Pensacola Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$57 Cheap Flights from Chicago to Pensacola in 2025

Q: What is the typical price of a round-trip flight between Chicago and Pensacola?

Prices are currently low for flights on this route. Typical prices usually range from $289 to $467. The lowest price recently found on this route was $133.

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

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

Trusted and free

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

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Chicago to Pensacola

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

10:39 am - 1:06 pmORD-PNS

2h 27mnonstop

2:15 pm - 4:52 pmPNS-ORD

2h 37mnonstop

$133United Airlines

Find Deal

Tue, Aug 12 - Tue, Aug 19

10:25 am - 3:05 pmMDW-PNS

4h 40m1 stop

4:45 pm - 6:55 pmPNS-MDW

2h 10mnonstop

$143Southwest

Find Deal

Sat, Sep 6 - Sat, Sep 13

8:20 am - 10:30 amMDW-PNS

2h 10mnonstop

4:45 pm - 6:55 pmPNS-MDW

2h 10mnonstop

$144Southwest

Find Deal

Sat, Sep 6 - Sat, Sep 13

11:25 am - 7:50 pmMDW-PNS

8h 25m2 stops

4:45 pm - 6:55 pmPNS-MDW

2h 10mnonstop

$148Southwest

Find Deal

Sat, Sep 6 - Sat, Sep 13

3:10 pm - 6:55 pmORD-PNS

3h 45m1 stop

7:35 am - 12:45 pmPNS-ORD

5h 10m1 stop

$153Southwest

Find Deal

Wed, Aug 13 - Wed, Aug 20

4:36 pm - 10:41 pmORD-PNS

6h 05m1 stop

6:00 am - 3:31 pmPNS-ORD

9h 31m1 stop

$168Spirit Airlines

Find Deal

Tue, Jul 22 - Thu, Jul 24

4:36 pm - 10:41 pmORD-PNS

6h 05m1 stop

6:00 am - 3:31 pmPNS-ORD

9h 31m1 stop

$171Spirit Airlines

Find Deal

Tue, Aug 5 - Thu, Aug 7

5:45 am - 10:50 amORD-PNS

5h 05m1 stop

6:00 am - 12:17 pmPNS-ORD

6h 17m1 stop

$177Delta

Find Deal

Tue, Aug 12 - Sat, Aug 16

4:22 pm - 8:39 pmMDW-PNS

4h 17m1 stop

5:00 pm - 9:12 pmPNS-MDW

4h 12m1 stop

$177Delta

Find Deal

Sat, Aug 9 - Sat, Aug 16

10:39 am - 1:06 pmORD-PNS

2h 27mnonstop

5:00 pm - 12:15 amPNS-ORD

7h 15m1 stop

$183United Airlines

Find Deal

Mon, Aug 11 - Mon, Aug 18

United Airlines flights from Chicago to Pensacola

Our best United Airlines deals on Chicago to Pensacola flight tickets

United Airlines

Aug 12

ORD10:39 amChicago O'Hare Intl

2h 27m

PNS1:06 pmPensacola

Aug 19

PNS2:15 pmPensacola

2h 37m

ORD4:52 pmChicago O'Hare Intl

$133

Find similar

United Airlines

Aug 11

ORD10:39 amChicago O'Hare Intl

2h 27m

PNS1:06 pmPensacola

Aug 18

PNS5:00 pmPensacola

7h 15m

1 stop

ORD12:15 amChicago O'Hare Intl

$183

Find similar

United Airlines

Aug 12

ORD10:39 amChicago O'Hare Intl

2h 27m

PNS1:06 pmPensacola

Aug 19

PNS2:15 pmPensacola

2h 37m

ORD4:52 pmChicago O'Hare Intl

$203

Find similar

Spirit Airlines flights from Chicago to Pensacola

Our best Spirit Airlines deals on Chicago to Pensacola flight tickets

Spirit Airlines

Jul 22

ORD4:36 pmChicago O'Hare Intl

6h 05m

1 stop

PNS10:41 pmPensacola

Jul 24

PNS6:00 amPensacola

9h 31m

1 stop

ORD3:31 pmChicago O'Hare Intl

$168

Find similar

Spirit Airlines

Aug 5

ORD4:36 pmChicago O'Hare Intl

6h 05m

1 stop

PNS10:41 pmPensacola

Aug 7

PNS6:00 amPensacola

9h 31m

1 stop

ORD3:31 pmChicago O'Hare Intl

$171

Find similar

Spirit Airlines

Aug 5

ORD4:36 pmChicago O'Hare Intl

6h 05m

1 stop

PNS10:41 pmPensacola

Aug 12

PNS6:00 amPensacola

9h 31m

1 stop

ORD3:31 pmChicago O'Hare Intl

$173

Find similar

How to get the cheapest flight ticket from Chicago to Pensacola

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

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Chicago and Pensacola?

What is the cheapest month to fly to Pensacola?

The cheapest month to fly to Pensacola from Chicago is in January. Flight prices, which tend to average around $298, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Pensacola from Chicago during April instead. Flights to Pensacola in April, while not as cheap as those in January, still average around $306.

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

On average, the least expensive day to fly to Pensacola from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $326. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $462.

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

The cheapest time of day to fly to Pensacola is in the afternoon when flights can be purchased for as low as $293. Flights to Pensacola are more costly in the morning, with an average ticket price of $402. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Pensacola flight route?

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

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

You are more likely to see cheaper flights to Pensacola from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Pensacola for around $362 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Pensacola from Chicago for as low as $257 on momondo.

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

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

How have Chicago to Pensacola flight prices changed over time?

As of July 2025, prices for Chicago to Pensacola flights are approximately 24% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Pensacola

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

Estimated round-trip price

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

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

Best Price Found	$57
Fastest flight time	2h 05m
Direct flights	Every day
Airports in Pensacola	1 airport

The best one-way flight to Pensacola from Chicago in the past 72 hours is $57. The best round-trip flight deal from Chicago to Pensacola found on momondo in the last 72 hours is $133.

The fastest flight from Chicago to Pensacola takes 2h 05m

Direct flights go from Chicago to Pensacola every day.

There is 1 airport near Pensacola: Pensacola (PNS)

Search flight deals

How far is Chicago to Pensacola by plane?
The distance between Chicago and Pensacola is about 791.2 mi. A reasonable flight in good conditions will take 2h 05m.
When did momondo last update prices for flights from Chicago to Pensacola Airport?
Prices for flights from Chicago to Pensacola Airport refresh daily.
How many operators does momondo search for flights from Chicago to Pensacola Airport?
As of July 2025, there are 5 operators available to choose from for flights from Chicago to Pensacola Airport.
How old do you have to be to fly from Chicago to Pensacola Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Pensacola Airport.
What documentation or ID do you need to fly to Pensacola Airport?
The travel and health documents required for your trip to Pensacola Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Pensacola Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Pensacola?
Based on momondo bookings for flights between Chicago and Pensacola, the leading plane model is Airbus A319, making up 27.62% of the total bookings. Other popular models include Airbus A320-100/200 with 25.41%, Boeing 737-700 with 9.76%, and Boeing 737-800 Passenger/BBJ2 (winglets) with 8.84%.
What is the most popular airline from Chicago to Pensacola?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to Pensacola is United Airlines (47% of total bookings). The next most popular airlines are Southwest (20%), American Airlines (12%), and Delta (11%).

Best airlines flying from Chicago to Pensacola

Compare and see reviews for airlines that fly from Chicago to Pensacola with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $118	Free Cancellation	Rating 6.3 8,055 reviews	Search Spirit Airlines flights
Delta	PriceFrom $196	Free Cancellation	Rating 8.0 7,952 reviews	Search Delta flights
Southwest	PriceFrom $222	Free Cancellation	Rating 8.0 4,250 reviews	Search Southwest flights
American Airlines	PriceFrom $228	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $235	Free Cancellation	Rating 7.4 8,846 reviews	Search United Airlines flights

Southwest Flights From Chicago to Pensacola
Southwest is one of the most popular airlines flying from Chicago to Pensacola, operating 8 flights/week on average for this route. A good Southwest flight deal for Chicago to Pensacola starts from $222 round-trip, up to an average price of $379. Our users have rated Southwest at 8.0/10.
United Airlines Flights From Chicago to Pensacola
Across 8,846 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Chicago to Pensacola about 4 times each week, with ticket deals ranging from $235 to $408. Price data is based on momondo searches in the last 72 hours.

Orange Beach

Pensacola Beach

Foley

Navarre Beach

Perdido Key

Navarre

Atmore

Milton

Gulf Breeze

Warrington

Evergreen

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Pensacola. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Chicago to Pensacola on momondo can be filtered to show those which offer flexible booking policies.

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

momondo helps you find the best flight between Chicago and Pensacola 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 Chicago to Pensacola right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Pensacola, momondo offers a useful price alert feature which will track prices for flights to Pensacola from Chicago and alert you when they change.

An easier way to manage your Pensacola 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

Tue 7/15

Tue 7/22

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Airports servicing Florida

Popular cities in the United States

Flights to New Yorkfrom $37

Flights to Los Angelesfrom $39

Flights to Miamifrom $38

Flights to Chicagofrom $58

Flights to Las Vegasfrom $16

Flights to Orlandofrom $36

Flights to San Franciscofrom $56

Flights to Washington, D.C.from $38

Flights to Bostonfrom $57

Flights to Dallasfrom $66

Flights to Atlantafrom $49

Flights to Seattlefrom $82

Cheap flights from Chicago to Pensacola from $57

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Pensacola departing on 11/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago to Pensacola

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

United Airlines flights from Chicago to Pensacola

Our best United Airlines deals on Chicago to Pensacola flight tickets

Spirit Airlines flights from Chicago to Pensacola

Our best Spirit Airlines deals on Chicago to Pensacola flight tickets

See travel insights to Pensacola from

How to get the cheapest flight ticket from Chicago to Pensacola

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 Chicago and Pensacola?

What is the cheapest month to fly to Pensacola?

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

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

What is the cheapest Chicago to Pensacola flight route?

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

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

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

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

How have Chicago to Pensacola flight prices changed over time?

As of July 2025, prices for Chicago to Pensacola flights are approximately 24% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Chicago to Pensacola?

American Airlines, United Airlines, and Southwest are the most popular carriers operating from Chicago to Pensacola

What airlines fly to Pensacola?

How many flights depart from Chicago to Pensacola on average per day?

The number of flights available between Chicago and Pensacola is 2 per day as of July 2025. The most frequent departure time is 10:00AM, with 100% of daily flights leaving at noon.

How many flights depart from Chicago to Pensacola on average per week?

As of July 2025, there are 18 flights per week flying from Chicago to Pensacola. The most common day of the week flights depart is Mon, with 22% of flights taking off on this day.

When to book flights from Chicago to Pensacola

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Pensacola

How far is Chicago to Pensacola by plane?

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

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

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

What documentation or ID do you need to fly to Pensacola Airport?

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

What is the most popular airline from Chicago to Pensacola?

Best airlines flying from Chicago to Pensacola

Compare and see reviews for airlines that fly from Chicago to Pensacola with momondo

Southwest Flights From Chicago to Pensacola

United Airlines Flights From Chicago to Pensacola

Traveling to a place near Pensacola?

Why use momondo?

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

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

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

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

An easier way to manage your Pensacola 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing Florida