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Cheap flights from Pensacola to Chicago from $114

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Pensacola to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
3:26 pm - 12:24 amPNS  Pensacola-ORD Chicago O'Hare Intl
8h 58m1 stop Denver Intl
Frontier Logo
6:30 am - 2:31 pmORD  Chicago O'Hare Intl-PNS Pensacola
8h 01m1 stop Denver Intl
$238Frontier
Fri, Oct 16 - Sun, Oct 18
Frontier Logo
8:15 pm - 7:02 pmPNS  Pensacola-ORD Chicago O'Hare Intl
22h 47m1 stop Orlando
Frontier Logo
6:30 am - 2:31 pmORD  Chicago O'Hare Intl-PNS Pensacola
8h 01m1 stop Denver Intl
$238Frontier
Thu, Oct 15 - Sun, Oct 18
Frontier Logo
3:26 pm - 12:24 amPNS  Pensacola-ORD Chicago O'Hare Intl
8h 58m1 stop Denver Intl
Frontier Logo
6:30 am - 2:31 pmORD  Chicago O'Hare Intl-PNS Pensacola
8h 01m1 stop Denver Intl
$238Frontier
Thu, Oct 15 - Sun, Oct 18
United Airlines Logo
2:22 pm - 5:02 pmPNS  Pensacola-ORD Chicago O'Hare Intl
2h 40mnonstop
United Airlines Logo
10:57 am - 1:26 pmORD  Chicago O'Hare Intl-PNS Pensacola
2h 29mnonstop
$319United Airlines
Tue, Nov 10 - Wed, Nov 11
United Airlines Logo
4:18 pm - 7:00 pmPNS  Pensacola-ORD Chicago O'Hare Intl
2h 42mnonstop
United Airlines Logo
10:57 am - 1:26 pmORD  Chicago O'Hare Intl-PNS Pensacola
2h 29mnonstop
$319United Airlines
Wed, Oct 21 - Wed, Oct 28
American Airlines Logo
2:59 pm - 5:53 pmPNS  Pensacola-ORD Chicago O'Hare Intl
2h 54mnonstop
American Airlines Logo
12:01 pm - 2:26 pmORD  Chicago O'Hare Intl-PNS Pensacola
2h 25mnonstop
$319American Airlines
Tue, Dec 29 - Fri, Jan 1
American Airlines Logo
2:52 pm - 5:49 pmPNS  Pensacola-ORD Chicago O'Hare Intl
2h 57mnonstop
American Airlines Logo
11:50 am - 2:22 pmORD  Chicago O'Hare Intl-PNS Pensacola
2h 32mnonstop
$319American Airlines
Tue, Nov 24 - Fri, Nov 27
American Airlines Logo
11:01 am - 1:56 pmPNS  Pensacola-ORD Chicago O'Hare Intl
2h 55mnonstop
American Airlines Logo
11:50 am - 2:22 pmORD  Chicago O'Hare Intl-PNS Pensacola
2h 32mnonstop
$319American Airlines
Mon, Nov 23 - Fri, Nov 27
Delta Logo
6:00 am - 12:13 pmPNS  Pensacola-ORD Chicago O'Hare Intl
6h 13m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:27 am - 12:34 pmORD  Chicago O'Hare Intl-PNS Pensacola
7h 07m1 stop Atlanta Hartsfield-Jackson
$339Delta
Tue, Oct 27 - Fri, Oct 30
Delta Logo
5:24 pm - 11:54 pmPNS  Pensacola-ORD Chicago O'Hare Intl
6h 30m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:30 am - 11:12 amORD  Chicago O'Hare Intl-PNS Pensacola
5h 42m1 stop Atlanta Hartsfield-Jackson
$339Delta
Sat, Nov 21 - Tue, Dec 1

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American Airlines flights from Pensacola to Chicago O'Hare Intl Airport

Our best American Airlines deals on Pensacola to Chicago O'Hare Intl Airport flight tickets
American Airlines
Dec 29
PNS2:59 pmPensacola
2h 54m
ORD5:53 pmChicago O'Hare Intl
Jan 1
ORD12:01 pmChicago O'Hare Intl
2h 25m
PNS2:26 pmPensacola
$319
American Airlines
Dec 29
PNS2:59 pmPensacola
2h 54m
ORD5:53 pmChicago O'Hare Intl
Jan 1
ORD12:05 pmChicago O'Hare Intl
7h 45m
1 stop
PNS7:50 pmPensacola
$329
American Airlines
Oct 8
PNS4:45 pmPensacola
7h 23m
1 stop
ORD12:08 amChicago O'Hare Intl
Oct 13
ORD8:05 amChicago O'Hare Intl
6h 54m
1 stop
PNS2:59 pmPensacola
$434

United Airlines flights from Pensacola to Chicago O'Hare Intl Airport

Our best United Airlines deals on Pensacola to Chicago O'Hare Intl Airport flight tickets
United Airlines
Oct 23
PNS4:18 pmPensacola
2h 42m
ORD7:00 pmChicago O'Hare Intl
Oct 25
ORD10:47 amChicago O'Hare Intl
2h 28m
PNS1:15 pmPensacola
$331
United Airlines
Oct 10
PNS4:18 pmPensacola
2h 42m
ORD7:00 pmChicago O'Hare Intl
Oct 13
ORD11:05 amChicago O'Hare Intl
2h 29m
PNS1:34 pmPensacola
$352
United Airlines
Sep 28
PNS4:18 pmPensacola
2h 42m
ORD7:00 pmChicago O'Hare Intl
Oct 5
ORD10:45 amChicago O'Hare Intl
2h 29m
PNS1:14 pmPensacola
$394

momondo Fare Finder

 
Use the filters below to find and compare flights from Pensacola to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PensacolaChicago

PNS Pensacola - ORD Chicago O'Hare Intl

PNSORD

Pensacola

Fri 10/16

3:26 pm-12:24 am

1 stop8h 58m

Chicago O'Hare Intl

Sun 10/18

6:30 am-2:31 pm

1 stop8h 01m

$238

PensacolaChicago

PNS Pensacola - ORD Chicago O'Hare Intl

PNSORD

Pensacola

Thu 10/15

8:15 pm-7:02 pm

1 stop22h 47m

Chicago O'Hare Intl

Sun 10/18

6:30 am-2:31 pm

1 stop8h 01m

$238

PensacolaChicago

PNS Pensacola - ORD Chicago O'Hare Intl

PNSORD

Pensacola

Thu 10/15

3:26 pm-12:24 am

1 stop8h 58m

Chicago O'Hare Intl

Sun 10/18

6:30 am-2:31 pm

1 stop8h 01m

$238
Quickest round-trip

PensacolaChicago

PNS Pensacola - ORD Chicago O'Hare Intl

PNSORD

Pensacola

Tue 11/10

2:22 pm-5:02 pm

Nonstop2h 40m

Chicago O'Hare Intl

Wed 11/11

10:57 am-1:26 pm

Nonstop2h 29m

$319

PensacolaChicago

PNS Pensacola - ORD Chicago O'Hare Intl

PNSORD

Pensacola

Wed 10/21

4:18 pm-7:00 pm

Nonstop2h 42m

Chicago O'Hare Intl

Wed 10/28

10:57 am-1:26 pm

Nonstop2h 29m

$319

PensacolaChicago

PNS Pensacola - ORD Chicago O'Hare Intl

PNSORD

Pensacola

Tue 12/29

2:59 pm-5:53 pm

Nonstop2h 54m

Chicago O'Hare Intl

Fri 1/1

12:01 pm-2:26 pm

Nonstop2h 25m

$319

PensacolaChicago

PNS Pensacola - ORD Chicago O'Hare Intl

PNSORD

Pensacola

Tue 11/24

2:52 pm-5:49 pm

Nonstop2h 57m

Chicago O'Hare Intl

Fri 11/27

11:50 am-2:22 pm

Nonstop2h 32m

$319

PensacolaChicago

PNS Pensacola - ORD Chicago O'Hare Intl

PNSORD

Pensacola

Mon 11/23

11:01 am-1:56 pm

Nonstop2h 55m

Chicago O'Hare Intl

Fri 11/27

11:50 am-2:22 pm

Nonstop2h 32m

$319

PensacolaChicago

PNS Pensacola - ORD Chicago O'Hare Intl

PNSORD

Pensacola

Tue 10/27

6:00 am-12:13 pm

1 stop6h 13m

Chicago O'Hare Intl

Fri 10/30

5:27 am-12:34 pm

1 stop7h 07m

$339

PensacolaChicago

PNS Pensacola - ORD Chicago O'Hare Intl

PNSORD

Pensacola

Sat 11/21

5:24 pm-11:54 pm

1 stop6h 30m

Chicago O'Hare Intl

Tue 12/1

5:30 am-11:12 am

1 stop5h 42m

$339

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 O'Hare Intl Airport

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 O'Hare Intl Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $266 to $429.
The lowest price recently found on this route was $238.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Pensacola averaging around $282.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday 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. On the other hand, Sunday is the most expensive day to depart from Pensacola because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $584.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Pensacola at noon is the least expensive time of day to depart. momondo users have found prices as low as $444 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $518. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Pensacola to Chicago O'Hare Intl flight route?

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

How far in advance should I book a flight from Pensacola to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Pensacola when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $353 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Pensacola for as low as $261 on momondo.

What cabin class options are available on Pensacola to Chicago O'Hare Intl Airport flights?

There are 4 cabin classes available to choose from on Pensacola to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Pensacola to Chicago O'Hare Intl Airport.

How have Pensacola to Chicago O'Hare Intl Airport flight prices changed over time?

As of September 2026, prices for Pensacola to Chicago O'Hare Intl Airport flights are approximately 82% more expensive when compared to flights at the same time last year.

When to book flights from Pensacola to Chicago O'Hare Intl Airport

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

Cheap Pensacola to Chicago O'Hare Intl Airport (PNS to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Pensacola to Chicago O'Hare Intl Airport

Best Price Found

$114

Fastest flight time

2h 39m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Pensacola in the past 72 hours is $114. The best round-trip flight deal from Pensacola to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $238.
The fastest flight from Pensacola to Chicago O'Hare Intl Airport takes 2h 39m
Direct flights go from Pensacola to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Pensacola to Chicago O'Hare Intl Airport

  • How far is Pensacola to Chicago O'Hare Intl by plane?

    A flight from Pensacola to Chicago O'Hare Intl will travel around 799.0 mi. Typically, this will take 2h 39m by plane in normal conditions.

  • When did momondo last update prices for flights from Pensacola Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Pensacola Airport to Chicago O'Hare Intl Airport are updated daily.

  • How many operators does momondo search for flights from Pensacola Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Pensacola Airport to Chicago O'Hare Intl Airport?

    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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Pensacola to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Pensacola to Chicago O'Hare Intl Airport?

Best airlines flying from Pensacola to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Pensacola to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $188Free CancellationRating
7.8
8,595 reviews
Search Delta flights
United AirlinesPriceFrom $207Free CancellationRating
7.4
10,233 reviews
Search United Airlines flights
American AirlinesPriceFrom $209Free CancellationRating
7.0
12,075 reviews
Search American Airlines flights

  • United Airlines Flights From Pensacola to Chicago O'Hare Intl Airport

    The lowest priced United Airlines flight from Pensacola to Chicago O'Hare Intl Airport from the last 72 hours was $207. Generally, United Airlines has 1 flight on this route every week with an average price of $358. United Airlines is rated 7.4/10 by our users.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
Merrillville
Rockford
South Haven
Rosemont
Gurnee
Oak Brook
Orland Park
Joliet
Naperville
New Buffalo
Kenosha
Hammond
Aurora
Racine
Elgin
Janesville
Evanston
Skokie

Why use momondo?

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

It is quick and easy to find Pensacola to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. momondo allows you to filter the results for Pensacola to Chicago flights to just show those with flexible booking policies.

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?

Of course. momondo tracks the price of Pensacola to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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