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Cheap flights from Chicago to Pensacola from $54

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 11/1. 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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Cheap round-trip flights

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Spirit Airlines Logo
6:00 am - 5:30 pmORD-PNS
11h 30m1 stop
Spirit Airlines Logo
10:28 am - 9:33 pmPNS-ORD
11h 05m1 stop
$205Spirit Airlines
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Mon, Oct 27 - Thu, Oct 30
Spirit Airlines Logo
6:00 am - 5:01 pmORD-PNS
11h 01m1 stop
Spirit Airlines Logo
10:28 am - 5:49 pmPNS-ORD
7h 21m1 stop
$206Spirit Airlines
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Wed, Oct 29 - Thu, Oct 30
United Airlines Logo
10:49 am - 1:15 pmORD-PNS
2h 26mnonstop
United Airlines Logo
2:17 pm - 4:48 pmPNS-ORD
2h 31mnonstop
$209United Airlines
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Tue, Nov 4 - Tue, Nov 11
American Airlines Logo
10:30 am - 1:00 pmORD-PNS
2h 30mnonstop
American Airlines Logo
1:32 pm - 4:11 pmPNS-ORD
2h 39mnonstop
$219American Airlines
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Wed, Nov 5 - Tue, Nov 11
Southwest Logo
10:50 am - 3:35 pmMDW-PNS
4h 45m1 stop
Southwest Logo
4:30 pm - 12:10 amPNS-MDW
7h 40m1 stop
$224Southwest
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Tue, Nov 4 - Thu, Nov 6
United Airlines Logo
10:49 am - 1:15 pmORD-PNS
2h 26mnonstop
United Airlines Logo
2:17 pm - 4:48 pmPNS-ORD
2h 31mnonstop
$226United Airlines
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Wed, Nov 19 - Sun, Nov 23
Delta Logo
5:20 am - 10:42 amORD-PNS
5h 22m1 stop
Delta Logo
7:00 am - 12:19 pmPNS-ORD
5h 19m1 stop
$229Delta
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Wed, Nov 5 - Tue, Nov 11
Delta Logo
6:00 am - 12:37 pmMDW-PNS
6h 37m1 stop
Delta Logo
5:00 pm - 11:40 pmPNS-MDW
6h 40m1 stop
$229Delta
Find Deal
Wed, Nov 5 - Tue, Nov 11
Southwest Logo
10:50 am - 3:35 pmMDW-PNS
4h 45m1 stop
Southwest Logo
12:10 pm - 8:35 pmPNS-MDW
8h 25m2 stops
$230Southwest
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Tue, Nov 4 - Thu, Nov 6
American Airlines Logo
10:30 am - 1:00 pmORD-PNS
2h 30mnonstop
American Airlines Logo
5:24 pm - 11:37 pmPNS-ORD
6h 13m1 stop
$240American Airlines
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Wed, Nov 5 - Mon, Nov 10

Spirit Airlines flights from Chicago to Pensacola

Our best Spirit Airlines deals on Chicago to Pensacola flight tickets
Spirit Airlines
Oct 27
ORD6:00 amChicago O'Hare Intl
11h 30m
1 stop
PNS5:30 pmPensacola
Oct 30
PNS10:28 amPensacola
11h 05m
1 stop
ORD9:33 pmChicago O'Hare Intl
$205
Find similar
Spirit Airlines
Oct 29
ORD6:00 amChicago O'Hare Intl
11h 01m
1 stop
PNS5:01 pmPensacola
Oct 30
PNS10:28 amPensacola
7h 21m
1 stop
ORD5:49 pmChicago O'Hare Intl
$206
Find similar
Spirit Airlines
Nov 4
ORD10:00 amChicago O'Hare Intl
9h 11m
2 stops
PNS7:11 pmPensacola
Nov 6
PNS11:17 amPensacola
11h 49m
1 stop
ORD11:06 pmChicago O'Hare Intl
$211
Find similar

United Airlines flights from Chicago to Pensacola

Our best United Airlines deals on Chicago to Pensacola flight tickets
United Airlines
Nov 4
ORD10:49 amChicago O'Hare Intl
2h 26m
PNS1:15 pmPensacola
Nov 11
PNS2:17 pmPensacola
2h 31m
ORD4:48 pmChicago O'Hare Intl
$209
Find similar
United Airlines
Nov 19
ORD10:49 amChicago O'Hare Intl
2h 26m
PNS1:15 pmPensacola
Nov 23
PNS2:17 pmPensacola
2h 31m
ORD4:48 pmChicago O'Hare Intl
$226
Find similar
United Airlines
Nov 13
ORD10:49 amChicago O'Hare Intl
2h 26m
PNS1:15 pmPensacola
Nov 17
PNS2:17 pmPensacola
2h 31m
ORD4:48 pmChicago O'Hare Intl
$230
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Pensacola 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 October 14, 2025.
Use the filters below to find and compare flights from Chicago to Pensacola that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 10/27

6:00 am-5:30 pm

1 stop11h 30m

Pensacola

Thu 10/30

10:28 am-9:33 pm

1 stop11h 05m

$205

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 10/29

6:00 am-5:01 pm

1 stop11h 01m

Pensacola

Thu 10/30

10:28 am-5:49 pm

1 stop7h 21m

$206

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 11/4

10:49 am-1:15 pm

Nonstop2h 26m

Pensacola

Tue 11/11

2:17 pm-4:48 pm

Nonstop2h 31m

$209

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 11/5

10:30 am-1:00 pm

Nonstop2h 30m

Pensacola

Tue 11/11

1:32 pm-4:11 pm

Nonstop2h 39m

$219

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 11/4

10:50 am-3:35 pm

1 stop4h 45m

Pensacola

Thu 11/6

4:30 pm-12:10 am

1 stop7h 40m

$224

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 11/19

10:49 am-1:15 pm

Nonstop2h 26m

Pensacola

Sun 11/23

2:17 pm-4:48 pm

Nonstop2h 31m

$226

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 11/5

5:20 am-10:42 am

1 stop5h 22m

Pensacola

Tue 11/11

7:00 am-12:19 pm

1 stop5h 19m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 11/5

6:00 am-12:37 pm

1 stop6h 37m

Pensacola

Tue 11/11

5:00 pm-11:40 pm

1 stop6h 40m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 11/4

10:50 am-3:35 pm

1 stop4h 45m

Pensacola

Thu 11/6

12:10 pm-8:35 pm

2 stops8h 25m

$230

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 11/5

10:30 am-1:00 pm

Nonstop2h 30m

Pensacola

Mon 11/10

5:24 pm-11:37 pm

1 stop6h 13m

$240

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 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?

The cheapest month to fly to Pensacola from Chicago is in September. Flight prices, which tend to average around $268, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Pensacola from Chicago during January instead. Flights to Pensacola in January, while not as cheap as those in September, still average around $298.

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 $314. 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 $397.

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 evening, with an average ticket price of $379. Departure times in the evening 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 $339 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 $305 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.

Can stopping save me money on Chicago to Pensacola flights?

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

How have Chicago to Pensacola flight prices changed over time?

As of October 2025, prices for Chicago to Pensacola flights are approximately 62% more expensive 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

$136

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Pensacola

1 airport
The best one-way flight to Pensacola from Chicago in the past 72 hours is $136. The best round-trip flight deal from Chicago to Pensacola found on momondo in the last 72 hours is $222.
The fastest flight from Chicago to Pensacola takes 2h 10m
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 24m.

  • 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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $118Free CancellationRating
6.3
8,092 reviews
Search Spirit Airlines flights
DeltaPriceFrom $196Free CancellationRating
7.9
7,973 reviews
Search Delta flights
SouthwestPriceFrom $214Free CancellationRating
8.0
4,235 reviews
Search Southwest flights
American AirlinesPriceFrom $217Free CancellationRating
7.2
11,045 reviews
Search American Airlines flights
United AirlinesPriceFrom $220Free CancellationRating
7.4
8,974 reviews
Search United Airlines flights

  • United Airlines Flights From Chicago to Pensacola

    United Airlines is one of the most popular airlines flying from Chicago to Pensacola, operating 7 flights/week on average for this route. A good United Airlines flight deal for Chicago to Pensacola starts from $220 round-trip, up to an average price of $380. Our users have rated United Airlines at 7.4/10.

Traveling to a place near Pensacola?

Book flights to Pensacola if you plan to visit one of these locations
Orange Beach
Pensacola Beach
Foley
Perdido Key
Navarre Beach
Navarre
Milton
Atmore
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.

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