What are the cheapest airlines flying from Philadelphia to Chicago round-trip?

Our cheapest airline available from Philadelphia to Chicago is Frontier. Our recent data shows that you can find tickets from as low as $161 on this airline. Additional options worth looking into are United Airlines and Southwest, starting at $167 and $167 round-trip. You may be able to fly from Philadelphia to Chicago for 30% less than the average price by searching for these airlines.

What are the cheapest airlines to fly from Philadelphia to Chicago one-way?

The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $83. However, be on the lookout for offers from Spirit Airlines and American Airlines, as they are both options that can get you from Philadelphia to Chicago for a low price.

How far ahead should I book a flight from Philadelphia to Chicago?

The price you pay for your flight from Philadelphia to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 69 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Philadelphia to Chicago?

Currently, August is the cheapest month in which you can book a flight from Philadelphia to Chicago (average of $245). Flying from Philadelphia to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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

Travelers seeking maximum savings on their Philadelphia to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Philadelphia to Chicago

The most flights from PHL to CHI are scheduled on a Monday (55 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (34 on average).

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the most popular routes from Philadelphia to Chicago?

Most travelers choose Philadelphia - Chicago O'Hare Intl, Philadelphia - Chicago Midway or Philadelphia - Chicago Greater Rockford when deciding on the best route from Philadelphia to Chicago.

What are the cheapest flights from Philadelphia to Chicago?

The cheapest flight price from Philadelphia to Chicago is $87. On average you can expect to pay $1,211. The most popular route, (Philadelphia - Chicago O'Hare Intl), can usually be booked for $118.

What are the most reliable airlines from Philadelphia to Chicago?

The top 3 most reliable airlines when flying from Philadelphia to Chicago are Air Canada (86%), ANA (86%) and SWISS (84%).

What are the most popular airlines that fly from Philadelphia to Chicago?

Before booking your flight from Philadelphia to Chicago check out the most popular airlines for this route: American Airlines, Delta or Frontier.

What is the cheapest day to fly round-trip from Philadelphia to Chicago?

It’s generally more expensive to depart on a Thursday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

How far in advance should I book a flight from Philadelphia to Chicago?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 12 days in advance, which can save you up to 11% on flights from Philadelphia to Chicago compared to booking the week you need them. Waiting 12 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $146. For sooner than that we have options available in the next 3 days from $235.

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

Due to multiple factors, expect to potentially pay more when booking in March. For low rates, September can be a great choice for travel to Chicago. Flights to Chicago from Philadelphia in September are about $233 on average during September, but can be found for as low as $51.

What is the cheapest time of day to fly from PHL to CHI?

It’s optimal to fly from Philadelphia to Chicago in the evening. By choosing this option you can save up to 40% on the cost of your flight, compared to a flight in the morning.

What airport do you fly from for flights from Philadelphia to Chicago?

Most people fly from Philadelphia (PHL) if they book a flight from Philadelphia to Chicago. On average, Philadelphia has 44 outbound flights to Chicago per day from 5 airlines. Philadelphia is conveniently located just 7.0 mi from Philadelphia’s city center.

Can I find deals for flights from Philadelphia to Chicago that include hotel bookings?

Yes. In addition to deals on Philadelphia to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Philadelphia to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Philadelphia to Chicago.

Can I find deals for business class flights from Philadelphia to Chicago?

Yes. Cheapflights offers flight deals from Philadelphia to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$83+ Flights from Philadelphia to Chicago

Round-trip from	$160 (Kiwi.com)
One-way from	$83 (Frontier)
Popular in	March
Cheapest in	September
Average price	$217
Good round-trip deal	$190 or less
Good one-way deal	$104 or less

Basic Economy on United allows a personal item only; no carry-on bags permitted.

United Economy Plus offers extra legroom seats towards the front of the economy cabin.

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$51	Average$134	FlexibilityNo cancel fee	On-time62%
Delta	Cheapest$118	Average$294	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$146	Average$300	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$155	Average$289	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$171	Average$303	FlexibilityNo cancel fee	On-time63%

$83+ Cheap flights from Philadelphia (PHL) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/8. Fares are subject to change and may not be available on all flights or dates of travel.

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Cheapflights Tip: The best prices from Philadelphia to Chicago are usually found in September or August, booked 69 days in advance, depart on a Friday or Thursday and return on a Thursday

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Cheapest flights from Philadelphia to ChicagoExplore the most affordable flight options available from Philadelphia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2025.

Explore the most affordable flight options available from Philadelphia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2025.

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The best insider tips for Philadelphia to Chicago flights

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Best time to book a flight from Philadelphia to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Philadelphia with our price prediction graph.

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Everything you need to know about your flight from Philadelphia to Chicago

How far ahead should I book a flight from Philadelphia to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Philadelphia to Chicago. Price data was last updated on June 27, 2025.

What is the cheapest month to book a flight from Philadelphia to Chicago?

What is the cheapest time of day to fly from PHL to CHI?

Find hourly flight availability from Philadelphia to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 30, 2025.

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

Use this chart to determine the cheapest time to fly round-trip from Philadelphia to Chicago. Price data was last updated on June 29, 2025.

Weekly flight availability from Philadelphia to Chicago

Explore weekly flight availability from Philadelphia to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 30, 2025.

Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Philadelphia to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Philadelphia to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly from for flights from Philadelphia to Chicago?

What are the cheapest airlines flying from Philadelphia to Chicago round-trip?

What are the cheapest airlines to fly from Philadelphia to Chicago one-way?

What are the most popular routes from Philadelphia to Chicago?

What are the most reliable airlines from Philadelphia to Chicago?

What are the cheapest flights from Philadelphia to Chicago?

Can I find deals for flights from Philadelphia to Chicago that include hotel bookings?

How can I find direct flights from Philadelphia to Chicago?

Can I find deals for business class flights from Philadelphia to Chicago?

What is the cheapest month to book a flight from Philadelphia to Chicago?

Traveling to a place near Philadelphia?

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Cheapest flights from Philadelphia to Chicago
Explore the most affordable flight options available from Philadelphia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2025.