S$199 Cheap Flights from Pensacola to Chicago

View S$199 flight on Sun, 31 Aug, 2025Opens in a new window

Popular airlines from Pensacola Intl. Airport (PNS) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Pensacola to Chicago (PNS-ORD)

Prices were available within the past 7 days and start at S$199 for one-way flights and S$431 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, 31 Aug - Tue, 2 Sep
PNS
Pensacola
ORD
Chicago
S$431 Return, found 1 day ago
S$431
Return
found 1 day ago
Select Delta flight, departing Sun, 31 Aug from Pensacola to Chicago, returning Tue, 2 Sep, priced at S$431 found 1 day ago
Delta
Sun, 31 Aug - Tue, 2 Sep
PNS
Pensacola
ORD
Chicago
S$443 Return, found 1 day ago
S$443
Return
found 1 day ago
Select Delta flight, departing Sun, 31 Aug from Pensacola to Chicago, returning Tue, 2 Sep, priced at S$443 found 1 day ago
United
Sun, 31 Aug - Tue, 2 Sep
PNS
Pensacola
ORD
Chicago
S$462 Return, found 1 day ago
S$462
Return
found 1 day ago
Select United flight, departing Sun, 31 Aug from Pensacola to Chicago, returning Tue, 2 Sep, priced at S$462 found 1 day ago
Delta
Sun, 31 Aug - Tue, 2 Sep
PNS
Pensacola
ORD
Chicago
S$463 Return, found 1 day ago
S$463
Return
found 1 day ago
Select Delta flight, departing Sun, 31 Aug from Pensacola to Chicago, returning Tue, 2 Sep, priced at S$463 found 1 day ago
Delta
Sun, 31 Aug - Tue, 2 Sep
PNS
Pensacola
ORD
Chicago
S$473 Return, found 1 day ago
S$473
Return
found 1 day ago
Select Delta flight, departing Sun, 31 Aug from Pensacola to Chicago, returning Tue, 2 Sep, priced at S$473 found 1 day ago
Delta
Sun, 31 Aug - Tue, 2 Sep
PNS
Pensacola
ORD
Chicago
S$476 Return, found 1 day ago
S$476
Return
found 1 day ago
Select Delta flight, departing Sun, 31 Aug from Pensacola to Chicago, returning Tue, 2 Sep, priced at S$476 found 1 day ago
American Airlines
Sun, 31 Aug - Tue, 2 Sep
PNS
Pensacola
ORD
Chicago
S$476 Return, found 1 day ago
S$476
Return
found 1 day ago
Select American Airlines flight, departing Sun, 31 Aug from Pensacola to Chicago, returning Tue, 2 Sep, priced at S$476 found 1 day ago
American Airlines
Sun, 31 Aug - Tue, 2 Sep
PNS
Pensacola
ORD
Chicago
S$487 Return, found 1 day ago
S$487
Return
found 1 day ago
Select American Airlines flight, departing Sun, 31 Aug from Pensacola to Chicago, returning Tue, 2 Sep, priced at S$487 found 1 day ago
Delta
Sun, 31 Aug - Tue, 2 Sep
PNS
Pensacola
ORD
Chicago
S$501 Return, found 1 day ago
S$501
Return
found 1 day ago
Select Delta flight, departing Sun, 31 Aug from Pensacola to Chicago, returning Tue, 2 Sep, priced at S$501 found 1 day ago
Delta
Sun, 31 Aug - Tue, 2 Sep
PNS
Pensacola
ORD
Chicago
S$506 Return, found 1 day ago
S$506
Return
found 1 day ago
Select Delta flight, departing Sun, 31 Aug from Pensacola to Chicago, returning Tue, 2 Sep, priced at S$506 found 1 day ago

Find the cheapest month to fly from Pensacola (PNS) to Chicago (ORD)

March is typically the cheapest month to fly

From S$147 - S$474 per traveller.

Graph displaying average flight prices per month

Pensacola to Chicago route information
Origin airport
Pensacola Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Return price
S$430
Distance
1272 km
Average flight time
2 hours 37 mins

Perfect flights from Pensacola to Chicago

Your Journey from Pensacola to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Pensacola to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, American Airlines, United. Our selection of flights from Pensacola Intl. to O'Hare Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Pensacola to Chicago Flights

Experience the joy of finding cheap flights from Pensacola Intl. to O'Hare Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$199 and roundtrip prices from S$431*.
 

Pre-Flight Essentials

Ensure a smooth journey from Pensacola to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Pensacola to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Pensacola to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Pensacola to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Pensacola to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from Pensacola Intl. Airport (PNS) to ORD?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price listed for a round-trip flight between Pensacola Airport and O'Hare Airport was S$431. Fares this cheap don't last forever, so make sure you book yours ASAP. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Pensacola Intl. Airport (PNS) to O'Hare Airport?
Every airline has its own set of terms and conditions. If you decide to cancel your holiday, visit our Customer Service Portal.
How do I find cheap flights from Pensacola Airport to O'Hare Intl. Airport (ORD) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Pensacola Airport to ORD flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD)?
The flight distance from Pensacola Intl. Airport (PNS) (PNS) to O'Hare Airport (ORD) is 1,300 kilometres. You'll be walking down the air bridge and collecting your baggage from the carousel before you know it.
Which airlines fly direct from PNS to O'Hare Airport?
If you want to fly directly from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD), United Airlines (UA) is a top choice. It operates 30 monthly flights between Pensacola and Chicago.
Are Pensacola Intl. Airport (PNS) to ORD flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Pensacola Intl. Airport (PNS) to ORD at the last minute could be your ticket to an awesome deal. However, it could end up costing a great deal more! If you'd rather avoid the risk, book well ahead of your departure date. In fact, Expedia has some of the best bargains up to 12 months in advance. If your preferred carrier hasn't released tickets yet, check back often as deals are updated on Expedia all the time.

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