Discover affordable flights from Philadelphia to Chicago with prices starting from $312. Book your journey today!
Philadelphia
PHL
→
Chicago
MDW
10/14/2025 – 10/21/2025
Cheap flight deals from Philadelphia to Chicago
Average price start from:
i
$192
Round-trip flights from Philadelphia to Chicago starting at $192. Book now for the best deals!
One-way from:
i
$99
One-way flights from Philadelphia to Chicago starting at $99. Great for flexible travel!
Cheapest day:
i
Thursday
Thursday is the cheapest day to fly from Philadelphia to Chicago. Save more by booking on this day!
Cheapest In:
i
$44
Nov 2025
Nov 2025 is the cheapest month to fly from Philadelphia to Chicago with prices starting at $44.
Find flight deals from Philadelphia to Chicago
Cheapest flights from Philadelphia to Chicago
ONEWAY FLIGHTS
LAST MINUTE
CHEAP FLIGHTS
BEST FLIGHTS
Explore the cheapest oneway flights from Philadelphia to Chicago spotted daily.
PHL
Philadelphia
PHL - Philadelphia • 2025-10-14 • 09:00
Unknown
60 min
MDW
Unknown City
$99
Non-stop • 60 min
PHL
Philadelphia
PHL - Philadelphia • 2025-10-14 • 09:00
Unknown
60 min
MDW
Unknown City
$102
Non-stop • 60 min
PHL
Philadelphia
PHL - Philadelphia • 2025-10-14 • 09:00
Unknown
60 min
MDW
Unknown City
$109
Non-stop • 60 min
PHL
Philadelphia
PHL - Philadelphia • 2025-10-14 • 09:00
Unknown
60 min
MDW
Unknown City
$150
Non-stop • 60 min
Price Trends & Analysis
Weekly Price Trends
Optimal pricing available on Thursday for flights to Chicago.
Monthly Price Trends
Lowest fares from Philadelphia to Chicago typically available in May.
Weather & Climate Information
Temperature
Chicago experiences a humid continental climate, with summer temperatures averaging 70-85°F (21-29°C) and winter temperatures ranging from 20-35°F (-6 to 2°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 late spring (May) or early fall (September to October), when the weather is mild and pleasant. These months also feature vibrant local events like the Chicago Blues Festival and the Chicago Gourmet, making your trip both enjoyable and culturally enriching.
Airlines at MDW
Book your journey from Philadelphia 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 Philadelphia 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, captivates with its stunning skyline and vibrant arts scene, where the echoes of jazz and blues fill the air. Stroll along the picturesque waterfront, marvel at the architectural wonders like the Willis Tower, and immerse yourself in the rich history at the Art Institute, home to masterpieces that tell stories of a diverse cultural tapestry. Visitors can savor world-renowned deep-dish pizza, explore eclectic neighborhoods, and experience the warmth of Midwestern hospitality, making every moment in Chicago a delightful adventure.
About Chicago
Travel to Chicago from Philadelphia 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 Philadelphia to Chicago
Book your journey from Philadelphia 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 Philadelphia to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional service.
Hotels in Chicago
Explore excellent hotel options near MDW Airport for your Chicago visit. These hotels near Chicago airport combine convenience with comfort, making them perfect for both short layovers and extended stays. Check for special offers and airport shuttle services.
Hotel
Category: Standard
Comfortable accommodations with modern amenities.
Location: Near airport
Hotel ID:
About Chicago
Travel to Chicago from Philadelphia 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, captivates with its stunning skyline and vibrant arts scene, where the echoes of jazz and blues fill the air. Stroll along the picturesque waterfront, marvel at the architectural wonders like the Willis Tower, and immerse yourself in the rich history at the Art Institute, home to masterpieces that tell stories of a diverse cultural tapestry. Visitors can savor world-renowned deep-dish pizza, explore eclectic neighborhoods, and experience the warmth of Midwestern hospitality, making every moment in Chicago a delightful adventure.
Hotels in Chicago
Explore excellent hotel options near MDW Airport for your Chicago visit. These hotels near Chicago airport combine convenience with comfort, making them perfect for both short layovers and extended stays. Check for special offers and airport shuttle services.
Hotel
Category: Standard
Comfortable accommodations with modern amenities.
Location: Near airport
Hotel ID:
Airlines Flying from Philadelphia to Chicago
Book your journey from Philadelphia 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 Philadelphia 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 Philadelphia to Chicago?
The cheapest fare is $99. For the best deals, consider booking during May and flying on Thursday.
How long is the flight from Philadelphia 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 Philadelphia to Chicago?
Multiple airlines operate this route including Frontier Airlines, Delta Air Lines, Southwest 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 May for additional savings.
Are there hotels near MDW Airport?
Yes, several hotels are conveniently located near MDW 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.
flight
Helps you find the cheapest flight deals to any destination with ease.
Browse through the best hotels and find exclusive deals.