Flights from Philadelphia to Chicago

Looking for flights from Philadelphia to Chicago? CompareWings brings you the latest offers, travel tips, non-stop airline options, and essential information to help you plan a smooth journey from the City of Brotherly Love to the Windy City.

Route Overview

The air route between Philadelphia and Chicago is a critical connection between two of America's historic and economic powerhouses. Frequent flights cater to business travelers, tourists, and students commuting between these major hubs.

The flight is quick and efficient, with an average non-stop duration of approximately 2 hours and 15 minutes. Flights depart from Philadelphia International Airport (PHL) and land at either Chicago O'Hare International (ORD) or Chicago Midway International Airport (MDW).

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When’s a good time to book a flight from Philadelphia to Chicago

What’s the cheapest day of the week to fly from Philadelphia to Chicago?

If you’re looking for a flight deals from Philadelphia to Chicago, it’s recommended to look for departures on Monday. Sunday tends to have higher prices.

What is the cheapest month to fly from Philadelphia to Chicago?

Historically, December has been the cheapest month for flights from Philadelphia to Chicago. On the other hand, the most expensive months tend to be May.

Airlines & Flight Options

  • American Airlines: A dominant carrier on this route, offering frequent daily non-stop flights between PHL and O'Hare (ORD). Ideal for business travelers who need schedule flexibility.
  • United Airlines: Another major player with a hub at O'Hare (ORD), offering numerous daily non-stop flights from PHL with strong westbound connection options.
  • Southwest Airlines: Popular among leisure travelers and students, Southwest flies non-stop from PHL to Midway (MDW), offering two free checked bags.
  • Frontier Airlines: Provides budget-friendly non-stop options to both ORD and MDW, ideal for travelers who pack light.
  • Spirit Airlines: A low-cost carrier offering affordable flights from PHL, typically into O'Hare (ORD).

Offers, Deals & Best Ways to Save

  • Best Booking Window: Book 3–6 weeks in advance to lock in the best fares.
  • Cheapest Days to Fly: Tuesdays and Wednesdays often offer the lowest prices.
  • Seasonal Trends: January and February are typically the cheapest months. Summer and holidays see higher pricing.
  • Airport Flexibility: Compare fares between O'Hare (ORD) and Midway (MDW). Midway is closer to the city center, but O'Hare has more flight options.

Tips to Get the Best Deals

  • Mix and Match Airlines: Consider flying one airline to Chicago and another back to Philadelphia to save money.
  • Pack Light: Frontier and Spirit charge additional fees for carry-ons and checked bags, so compare the total cost before booking.
  • Check Nearby Airports: Trenton-Mercer (TTN) sometimes offers alternatives, but direct PHL–CHI flights are usually the most convenient.

Travel Tips for PHL → CHI Flyers

  • Time Zone: Chicago (CT) is one hour behind Philadelphia (ET), so you gain an hour when flying west.
  • Airport Transportation in Chicago:
    • From O'Hare (ORD): The CTA Blue Line train takes about 45 minutes to downtown and costs $5. Taxis and rideshares cost $40–$60 depending on traffic.
    • From Midway (MDW): The CTA Orange Line reaches the Loop in about 25 minutes for $2.50. Rideshares typically cost $25–$40.
  • Weather:
    • Winter: Expect cold temperatures, wind, and snow. Bring winter layers, gloves, and boots.
    • Summer: Warm, humid weather makes it ideal for exploring Lake Michigan and outdoor attractions.

Frequently Asked Questions

The average non-stop flight time is approximately 2 hours and 15 minutes.

It depends on your final destination. Midway (MDW) is closer to downtown and generally less congested. O'Hare (ORD) is larger, has more international connections, and is convenient for the northern suburbs.

American, United, Southwest, Frontier, and Spirit all operate non-stop flights between Philadelphia and Chicago.

January is typically the cheapest month to fly, as it is the off-peak season for travel to Chicago.

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