Book your flight from Pensacola (PNS) to Chicago (MDW) at the best prices. Fares start from $283.
Pensacola
PNS
→
Chicago
MDW
11/09/2025 – 11/16/2025
Cheap flight deals from Pensacola to Chicago
Average price start from:
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$140
Round-trip flights from Pensacola to Chicago starting at $140. Book now for the best deals!
One-way from:
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$66
One-way flights from Pensacola to Chicago starting at $66. 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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$68
May 2025
May 2025 is the cheapest month to fly from Pensacola to Chicago with prices starting at $68.
Find flight deals from Pensacola to Chicago
Cheapest flights from Pensacola to Chicago
ONEWAY FLIGHTS
LAST MINUTE
CHEAP FLIGHTS
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Explore the cheapest oneway flights from Pensacola to Chicago spotted daily.
PNS
Pensacola
PNS - Pensacola • 2025-11-09 • 09:00
Unknown
60 min
MDW
Unknown City
$66
Non-stop • 60 min
PNS
Pensacola
PNS - Pensacola • 2025-11-09 • 09:00
Unknown
60 min
MDW
Unknown City
$99
Non-stop • 60 min
PNS
Pensacola
PNS - Pensacola • 2025-11-09 • 09:00
Unknown
60 min
MDW
Unknown City
$109
Non-stop • 60 min
PNS
Pensacola
PNS - Pensacola • 2025-11-09 • 09:00
Unknown
60 min
MDW
Unknown City
$157
Non-stop • 60 min
Price Trends & Analysis
Monthly Price Trends
The cheapest month for flights from Pensacola to Chicago is April.
Weather & Climate Information
Temperature
Chicago experiences cold winters with temperatures averaging 20°F to 30°F (-6°C to -1°C) and warm summers ranging from 70°F to 85°F (21°C to 29°C). The best times for comfortable travel are spring (April to June) and early fall (September to October), when temperatures are mild and humidity is lower.
Rainfall
The best time to visit Chicago is during late spring (May to June) when the weather is pleasantly warm and outdoor festivals, like the Chicago Blues Festival, are in full swing. Fall (September to October) also offers beautiful foliage, comfortable temperatures, and events like the Chicago Gourmet, making it an ideal time for tourists.
Airlines at MDW
Book your journey from Pensacola to Chicago with leading airlines including Frontier Airlines, Delta Air Lines, Southwest Airlines. 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, dazzles with its stunning skyline and vibrant cultural tapestry, blending rich history with modern flair. Explore the iconic Millennium Park, where the shimmering Cloud Gate invites reflection, and delve into the world-class art at the Art Institute, home to masterpieces that span centuries. Stroll along the picturesque Lake Michigan shoreline, savor deep-dish pizza, and immerse yourself in the lively music scene, from blues to jazz, as you experience the heart and soul of a city that never ceases to inspire.
About Chicago
Explore the wonders of Chicago on your journey from Pensacola. This remarkable destination blends cultural treasures with modern amenities, creating an enriching travel experience. Consider visiting during off-peak seasons for better value and fewer crowds.
Airlines Flying from Pensacola to Chicago
Book your journey from Pensacola to Chicago with leading airlines including Frontier Airlines, Delta Air Lines, Southwest Airlines. 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
Discover top-rated hotels near MDW Airport for your stay in Chicago. These accommodations offer excellent connectivity to MDW Airport and provide modern amenities for business and leisure travelers. Book early to secure the best rates and availability.
Hotel
Category: Standard
Comfortable accommodations with modern amenities.
Location: Near airport
Hotel ID:
About Chicago
Explore the wonders of Chicago on your journey from Pensacola. This remarkable destination blends cultural treasures with modern amenities, creating an enriching travel experience. Consider visiting during off-peak seasons for better value and fewer crowds.
Places to Visit in Chicago
Chicago, the Windy City, dazzles with its stunning skyline and vibrant cultural tapestry, blending rich history with modern flair. Explore the iconic Millennium Park, where the shimmering Cloud Gate invites reflection, and delve into the world-class art at the Art Institute, home to masterpieces that span centuries. Stroll along the picturesque Lake Michigan shoreline, savor deep-dish pizza, and immerse yourself in the lively music scene, from blues to jazz, as you experience the heart and soul of a city that never ceases to inspire.
Hotels in Chicago
Discover top-rated hotels near MDW Airport for your stay in Chicago. These accommodations offer excellent connectivity to MDW Airport and provide modern amenities for business and leisure travelers. Book early to secure the best rates and availability.
Hotel
Category: Standard
Comfortable accommodations with modern amenities.
Location: Near airport
Hotel ID:
Airlines Flying from Pensacola to Chicago
Book your journey from Pensacola to Chicago with leading airlines including Frontier Airlines, Delta Air Lines, Southwest Airlines. 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's the lowest price for flights from Pensacola to Chicago?
You can find flights starting from $66. For better deals, book during April and choose Wednesday departures.
How long is the journey from Pensacola to Chicago?
The average flight time is about 10-15 hours, with most routes including one stopover for better pricing and comfort.
What airlines operate flights on this route?
Several airlines serve this route including Frontier Airlines, Delta Air Lines, Southwest Airlines. Research current schedules and compare prices for the best deal.
How far in advance should I book?
For the best prices, book 2-3 months ahead and consider traveling during April when prices are typically lower.
What accommodation options are near MDW Airport?
MDW Airport has several nearby hotels with shuttle services, making it convenient for travelers with early or late flights.
What attractions can I visit in Chicago?
Chicago features a wonderful combination of historical sites and modern attractions. The best time to visit is during pleasant weather months for optimal sightseeing.
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