Find cheap flight tickets from Pensacola (PNS) to Chicago (ORD). Cheapest fare starts from $321.
Pensacola
PNS
→
Chicago
ORD
10/20/2025 – 10/27/2025
Cheap flight deals from Pensacola to Chicago
Average price start from:
i
$140
Round-trip flights from Pensacola to Chicago starting at $140. Book now for the best deals!
One-way from:
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$53
One-way flights from Pensacola to Chicago starting at $53. Great for flexible travel!
Cheapest day:
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Wednesday
Wednesday is the cheapest day to fly from Pensacola to Chicago. Save more by booking on this day!
Cheapest In:
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$146
Apr 2025
Apr 2025 is the cheapest month to fly from Pensacola to Chicago with prices starting at $146.
Find flight deals from Pensacola to Chicago
Cheapest flights from Pensacola to Chicago
ONEWAY FLIGHTS
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Explore the cheapest oneway flights from Pensacola to Chicago spotted daily.
PNS
Pensacola
PNS - Pensacola • 2025-10-20 • 09:00
Unknown
60 min
ORD
Unknown City
$53
Non-stop • 60 min
PNS
Pensacola
PNS - Pensacola • 2025-10-20 • 09:00
Unknown
60 min
ORD
Unknown City
$63
Non-stop • 60 min
PNS
Pensacola
PNS - Pensacola • 2025-10-20 • 09:00
Unknown
60 min
MSP
Unknown City
$84
Non-stop • 60 min
PNS
Pensacola
PNS - Pensacola • 2025-10-20 • 09:00
Unknown
60 min
MKE
Unknown City
$96
Non-stop • 60 min
PNS
Pensacola
PNS - Pensacola • 2025-10-20 • 09:00
Unknown
60 min
ORD
Unknown City
$99
Non-stop • 60 min
PNS
Pensacola
PNS - Pensacola • 2025-10-20 • 09:00
Unknown
60 min
ORD
Unknown City
$106
Non-stop • 60 min
PNS
Pensacola
PNS - Pensacola • 2025-10-20 • 09:00
Unknown
60 min
MSP
Unknown City
$109
Non-stop • 60 min
PNS
Pensacola
PNS - Pensacola • 2025-10-20 • 09:00
Unknown
60 min
MSP
Unknown City
$115
Non-stop • 60 min
PNS
Pensacola
PNS - Pensacola • 2025-10-20 • 09:00
Unknown
60 min
ORD
Unknown City
$115
Non-stop • 60 min
PNS
Pensacola
PNS - Pensacola • 2025-10-20 • 09:00
Unknown
60 min
ORD
Unknown City
$120
Non-stop • 60 min
PNS
Pensacola
PNS - Pensacola • 2025-10-20 • 09:00
Unknown
60 min
MSP
Unknown City
$159
Non-stop • 60 min
PNS
Pensacola
PNS - Pensacola • 2025-10-20 • 09:00
Unknown
60 min
ATW
Unknown City
$165
Non-stop • 60 min
Price Trends & Analysis
Monthly Price Trends
Lowest fares from Pensacola to Chicago typically available in March.
Weather & Climate Information
Temperature
Chicago experiences a humid continental climate, with summer temperatures averaging 70-85°F (21-29°C) and winter lows often dropping to 20°F (-6°C). The best times for comfortable travel are late spring (May) and early fall (September-October), when temperatures are mild and precipitation is relatively low.
Rainfall
The best time to visit Chicago is from late spring to early fall, particularly May through September, when the weather is warm and pleasant. This period also features vibrant local festivals, outdoor events, and a lively atmosphere, making it ideal for exploring the city's attractions.
Airlines at Chicago
Book your journey from Pensacola to Chicago with leading airlines including Frontier Airlines, Spirit Airlines, United Airlines, Delta Air Lines. These carriers provide excellent connectivity and multiple daily options for convenient travel.
The typical flight time is about 10-15 hours, with most flights featuring one stopover for better pricing and route optimization. When traveling from Pensacola to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional service.
Places to Visit in Chicago
Chicago, the Windy City, pulses with vibrant energy, blending stunning architecture and rich history along its iconic skyline. Visitors can marvel at the art-filled halls of the Art Institute, stroll through Millennium Park's lush landscapes, and savor a deep-dish pizza that’s a culinary rite of passage. As you wander the bustling streets, the rhythm of jazz and blues fills the air, inviting you to experience the city's dynamic cultural tapestry that promises unforgettable memories at every turn.
About Chicago
Travel to Chicago from Pensacola for an unforgettable experience. This vibrant destination offers a perfect blend of culture, history, and modern attractions. The best time to visit is during off-peak seasons for better deals and fewer crowds.
Airlines Flying from Pensacola to Chicago
Book your journey from Pensacola to Chicago with leading airlines including Frontier Airlines, Spirit Airlines, United Airlines, Delta Air Lines. These carriers provide excellent connectivity and multiple daily options for convenient travel.
The typical flight time is about 10-15 hours, with most flights featuring one stopover for better pricing and route optimization. When traveling from Pensacola to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional service.
Hotels in Chicago
Accommodations near ORD Airport provide excellent connectivity for travelers visiting Chicago. Look for hotels with shuttle services and modern amenities.
About Chicago
Travel to Chicago from Pensacola for an unforgettable experience. This vibrant destination offers a perfect blend of culture, history, and modern attractions. The best time to visit is during off-peak seasons for better deals and fewer crowds.
Places to Visit in Chicago
Chicago, the Windy City, pulses with vibrant energy, blending stunning architecture and rich history along its iconic skyline. Visitors can marvel at the art-filled halls of the Art Institute, stroll through Millennium Park's lush landscapes, and savor a deep-dish pizza that’s a culinary rite of passage. As you wander the bustling streets, the rhythm of jazz and blues fills the air, inviting you to experience the city's dynamic cultural tapestry that promises unforgettable memories at every turn.
Hotels in Chicago
Accommodations near ORD Airport provide excellent connectivity for travelers visiting Chicago. Look for hotels with shuttle services and modern amenities.
Airlines Flying from Pensacola to Chicago
Book your journey from Pensacola to Chicago with leading airlines including Frontier Airlines, Spirit Airlines, United Airlines, Delta Air Lines. These carriers provide excellent connectivity and multiple daily options for convenient travel.
The typical flight time is about 10-15 hours, with most flights featuring one stopover for better pricing and route optimization. When traveling from Pensacola to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional service.
Frequently Asked Questions
What is the cheapest flight from Pensacola to Chicago?
The cheapest fare is $53. For the best deals, consider booking during March and flying on Wednesday.
How long is the flight from Pensacola to Chicago?
Average flight time is around 10-15 hours, depending on layovers and the chosen route. Most flights include one stopover for optimal pricing.
Which airlines fly from Pensacola to Chicago?
Multiple airlines operate this route including Frontier Airlines, Spirit Airlines, United Airlines. Check current schedules and availability for the best options.
What is the best time to book flights?
Booking 2–3 months in advance usually gives the best prices. Consider flying during March for additional savings.
Are there hotels near ORD Airport?
Yes, several hotels are conveniently located near ORD Airport, including options with shuttle services for easy airport access.
What should I know about Chicago?
Chicago offers a perfect blend of culture, history, and modern attractions. The best time to visit is during pleasant weather months for optimal experiences.
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