Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Pensacola to Chicago from $93

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 5/27. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

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

Trusted and free

Trusted and free

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

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Pensacola to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
7:36 pm - 8:32 pm
PNS
-
ORD
24h 56m
1 stop
Frontier Logo
9:37 pm - 6:41 pm
ORD
-
PNS
21h 04m
1 stop
$191Frontier
Mon, May 11 - Fri, May 15
Frontier Logo
1:26 pm - 11:13 pm
PNS
-
ORD
9h 47m
1 stop
Frontier Logo
5:30 pm - 12:57 pm
ORD
-
PNS
19h 27m
1 stop
$196Frontier
Thu, May 14 - Sat, May 16
Multiple Airlines Logo
4:48 pm - 11:13 pm
PNS
-
ORD
6h 25m
1 stop
Multiple Airlines Logo
1:50 pm - 3:58 pm
ORD
-
PNS
26h 08m
2 stops
$202Multiple Airlines
Wed, May 27 - Wed, Jun 3
Frontier Logo
7:36 pm - 8:32 pm
PNS
-
ORD
24h 56m
1 stop
Frontier Logo
9:37 pm - 6:41 pm
ORD
-
PNS
21h 04m
1 stop
$212Frontier
Tue, May 19 - Wed, May 27
Frontier Logo
7:36 pm - 8:32 pm
PNS
-
ORD
24h 56m
1 stop
Frontier Logo
3:55 pm - 12:41 pm
ORD
-
PNS
20h 46m
1 stop
$217Frontier
Mon, May 11 - Wed, May 13
Spirit Airlines Logo
4:48 pm - 10:14 pm
PNS
-
ORD
5h 26m
1 stop
Spirit Airlines Logo
5:05 am - 12:46 pm
ORD
-
PNS
7h 41m
1 stop
$218Spirit Airlines
Fri, May 15 - Sat, May 16
Multiple Airlines Logo
4:48 pm - 10:14 pm
PNS
-
ORD
5h 26m
1 stop
Multiple Airlines Logo
5:11 pm - 1:59 pm
ORD
-
PNS
20h 48m
1 stop
$222Multiple Airlines
Wed, May 20 - Wed, May 27
Multiple Airlines Logo
2:46 pm - 12:37 pm
PNS
-
ORD
21h 51m
1 stop
Multiple Airlines Logo
7:52 am - 2:36 pm
ORD
-
PNS
6h 44m
1 stop
$224Multiple Airlines
Thu, Jun 4 - Fri, Jun 19
Multiple Airlines Logo
4:48 pm - 10:14 pm
PNS
-
ORD
5h 26m
1 stop
Multiple Airlines Logo
9:37 pm - 6:41 pm
ORD
-
PNS
21h 04m
1 stop
$228Multiple Airlines
Thu, May 28 - Wed, Jun 3
Multiple Airlines Logo
1:26 pm - 11:13 pm
PNS
-
ORD
9h 47m
1 stop
Multiple Airlines Logo
5:05 am - 5:03 pm
ORD
-
PNS
11h 58m
1 stop
$229Multiple Airlines
Thu, May 14 - Sun, May 17

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

Our best Spirit Airlines deals on Pensacola to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
May 15
PNS4:48 pmPensacola
5h 26m
1 stop
ORD10:14 pmChicago O'Hare Intl
May 16
ORD5:05 amChicago O'Hare Intl
7h 41m
1 stop
PNS12:46 pmPensacola
$218
Spirit Airlines
May 24
PNS4:48 pmPensacola
5h 26m
1 stop
ORD10:14 pmChicago O'Hare Intl
May 31
ORD5:05 amChicago O'Hare Intl
11h 58m
1 stop
PNS5:03 pmPensacola
$238
Spirit Airlines
Jul 3
PNS12:07 pmPensacola
11h 52m
1 stop
ORD11:59 pmChicago O'Hare Intl
Jul 7
ORD5:10 amChicago O'Hare Intl
9h 28m
1 stop
PNS2:38 pmPensacola
$240

Frontier flights from Pensacola to Chicago O'Hare Intl Airport

Our best Frontier deals on Pensacola to Chicago O'Hare Intl Airport flight tickets
Frontier
May 11
PNS7:36 pmPensacola
24h 56m
1 stop
ORD8:32 pmChicago O'Hare Intl
May 15
ORD9:37 pmChicago O'Hare Intl
21h 04m
1 stop
PNS6:41 pmPensacola
$191
Frontier
May 14
PNS1:26 pmPensacola
9h 47m
1 stop
ORD11:13 pmChicago O'Hare Intl
May 16
ORD5:30 pmChicago O'Hare Intl
19h 27m
1 stop
PNS12:57 pmPensacola
$196
Frontier
May 19
PNS7:36 pmPensacola
24h 56m
1 stop
ORD8:32 pmChicago O'Hare Intl
May 27
ORD9:37 pmChicago O'Hare Intl
21h 04m
1 stop
PNS6:41 pmPensacola
$212

momondo Fare Finder

 
Customize your flight search to find flights from Pensacola to Chicago O'Hare Intl Airport 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 April 30, 2026.
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 - ORD

PNSORD

Pensacola

Mon 5/11

7:36 pm-8:32 pm

1 stop24h 56m

Chicago O'Hare Intl

Fri 5/15

9:37 pm-6:41 pm

1 stop21h 04m

$191

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 5/14

1:26 pm-11:13 pm

1 stop9h 47m

Chicago O'Hare Intl

Sat 5/16

5:30 pm-12:57 pm

1 stop19h 27m

$196

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 5/27

4:48 pm-11:13 pm

1 stop6h 25m

Chicago O'Hare Intl

Wed 6/3

1:50 pm-3:58 pm

2 stops26h 08m

$202

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 5/19

7:36 pm-8:32 pm

1 stop24h 56m

Chicago O'Hare Intl

Wed 5/27

9:37 pm-6:41 pm

1 stop21h 04m

$212

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Mon 5/11

7:36 pm-8:32 pm

1 stop24h 56m

Chicago O'Hare Intl

Wed 5/13

3:55 pm-12:41 pm

1 stop20h 46m

$217
Quickest round-trip

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 5/15

4:48 pm-10:14 pm

1 stop5h 26m

Chicago O'Hare Intl

Sat 5/16

5:05 am-12:46 pm

1 stop7h 41m

$218

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 5/20

4:48 pm-10:14 pm

1 stop5h 26m

Chicago O'Hare Intl

Wed 5/27

5:11 pm-1:59 pm

1 stop20h 48m

$222

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 6/4

2:46 pm-12:37 pm

1 stop21h 51m

Chicago O'Hare Intl

Fri 6/19

7:52 am-2:36 pm

1 stop6h 44m

$224

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 5/28

4:48 pm-10:14 pm

1 stop5h 26m

Chicago O'Hare Intl

Wed 6/3

9:37 pm-6:41 pm

1 stop21h 04m

$228

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 5/14

1:26 pm-11:13 pm

1 stop9h 47m

Chicago O'Hare Intl

Sun 5/17

5:05 am-5:03 pm

1 stop11h 58m

$229

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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?

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

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Pensacola averaging around $277.

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 Thursday when prices can be found for as low as $384. 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 $556.

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 $417 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $653. 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 $317 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 $196 on momondo.

Can stopping save me money on Pensacola to Chicago O'Hare Intl Airport flights?

You could potentially save up to 12% on your flight if you consider stops on a Pensacola to Chicago O'Hare Intl Airport flight.

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

As of April 2026, prices for Pensacola to Chicago O'Hare Intl Airport flights are approximately 4% 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

$225

Fastest flight time

2h 30m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Pensacola in the past 72 hours is $225. The best round-trip flight deal from Pensacola to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $369.
The fastest flight from Pensacola to Chicago O'Hare Intl Airport takes 2h 30m
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 30m 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
Spirit AirlinesPriceFrom $173Free CancellationRating
6.3
8,634 reviews
Search Spirit Airlines flights
DeltaPriceFrom $196Free CancellationRating
7.9
8,463 reviews
Search Delta flights
United AirlinesPriceFrom $207Free CancellationRating
7.4
9,677 reviews
Search United Airlines flights
American AirlinesPriceFrom $209Free CancellationRating
7.1
11,683 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 3 flights on this route every week with an average price of $303. United Airlines is rated 7.4/10 by our users.

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

    Across 11,683 American Airlines reviews on momondo, the average score is 7.1/10. American Airlines flies from Pensacola to Chicago O'Hare Intl Airport about 7 times each week, with ticket deals ranging from $209 to $336. Price data is based on momondo searches in the last 72 hours.

Traveling to a place near Chicago?

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

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.

An easier way to manage your Chicago O'Hare Intl Airport 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
Sat 5/30
Sat 6/6
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago