Cheap Flights from Philadelphia To Chicago (Phl To Ord)

Phl
Philadelphia
Ord
Chicago
21 Jan 2026 - 28 Jan 2026
Phl
Philadelphia
Ord
Chicago
15 Jan 2026 - 22 Jan 2026
Phl
Philadelphia
Ord
Chicago
21 Jan 2026 - 28 Jan 2026
Phl
Philadelphia
Ord
Chicago
16 Jan 2026 - 23 Jan 2026
Phl
Philadelphia
Ord
Chicago
20 Jan 2026 - 27 Jan 2026
Phl
Philadelphia
Ord
Chicago
21 Jan 2026 - 28 Jan 2026

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When Is the Best Time to Book a Flight from Philadelphia To Chicago?

Cheapest Day of the Week to Fly from Philadelphia To Chicago

If you’re hunting for affordable airfare, Monday is typically the best day to book or depart for Philadelphia. Flights on Sundays generally cost more, so avoiding weekend departures can help you save.

Cheapest Month to Fly from Philadelphia To Chicago

Historically, December stands out as the most budget-friendly month for flights on this route. In contrast, May is usually one of the most expensive months to travel from Philadelphia To Chicago, making early planning essential if you’re flying during spring.

CompareWings Tips to Save More on a Philadelphia To Chicago Flight

Travelers looking to fly from Philadelphia To Chicago without breaking the bank need to look beyond the sticker price. Here is how you can slash your travel costs for this trip.

  • Be Flexible with Travel Dates: Flights from Philadelphia To Chicago can vary significantly in price depending on the day of the week. Mid-week departures (Tuesday and Wednesday) are often cheaper than weekend getaways.
  • Use a Flight Comparison Tool: Airfare on the Phl To Ord route changes frequently. Using a comparison tool like CompareWings helps you track fluctuating prices and get notified instantly when fares drop.
  • Check Alternative Airports: Chicago may be served by secondary airports. Sometimes flying into a smaller regional hub nearby and taking a short train ride can save you a significant amount compared to landing at the main international airport.
Popular airlines offer Flights from Philadelphia To Chicago (Phl To Ord)

Route Overview

The air route between Philadelphia and Chicago is a vital connection between two of America’s historic and economic powerhouses. This route serves business travelers, tourists, and students commuting between these major hubs.

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


Airlines & Flight Options


Offers, Deals & Best Ways to Save

Tips to Get the Best Deals:


Travel Tips for PHL → CHI Flyers

Frequently Asked Questions

To secure the best airfare, compare prices across multiple airlines on CompareWings. Use flexible date search, set fare alerts, and check nearby airports. These tools help you quickly identify the lowest prices for the Phl–Ord route.


Several major airlines operate this route throughout the year. With CompareWings, you can view all available carriers, flight schedules, aircraft types, and fare options for travel between Philadelphia and Chicago in one place.


Flight prices for the Philadelphia–Chicago route fluctuate based on travel season, demand, and booking window. Generally, booking a few weeks in advance and avoiding peak holiday dates can help you find cheaper fares. CompareWings price alerts can monitor this route for you.


Direct flight availability depends on the airline operating this route. CompareWings allows you to filter results by nonstop, one-stop, and connecting flights so you can easily see which options operate between Phl and Ord on your preferred travel dates.

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