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$89+ 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 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
May 17 — May 241
Sun 5/17
Sun 5/24
1 adult, Economy
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Find cheap flights from Philadelphia to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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Cheapflights Tip: The best prices from Philadelphia to Chicago are usually found in January or September, booked 85 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap flight deals from Philadelphia to Chicago

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 April 17, 2026.

This Frontier deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:06 pm
PHL
-
ORD
Nonstop2h 38m
Frontier
Mon 5/186:55 am
ORD
-
PHL
1 stop11h 19m
Frontier
Deal found 4/12$184
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/291:30 pm
PHL
-
ORD
1 stop11h 54m
Multiple Airlines
Fri 5/12:20 pm
ORD
-
PHL
Nonstop2h 14m
Multiple Airlines
Deal found 4/14$185
This Frontier deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/234:35 pm
PHL
-
MDW
1 stop6h 27m
Frontier
Thu 5/286:00 am
MDW
-
PHL
1 stop12h 14m
Frontier
Deal found 4/12$185
This CheapOair deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/215:45 am
PHL
-
ORD
1 stop28h 51m
Spirit Airlines
Tue 4/287:15 pm
ORD
-
PHL
1 stop27h 22m
Spirit Airlines
Deal found 4/13$186
This Super.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:05 am
PHL
-
MDW
1 stop16h 47m
Frontier
Tue 4/286:10 am
MDW
-
PHL
1 stop6h 11m
Frontier
Deal found 4/13$186
This Super.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:35 pm
PHL
-
ORD
1 stop24h 57m
Frontier
Sun 5/103:44 pm
ORD
-
PHL
1 stop8h 00m
Frontier
Deal found 4/14$187
This Trip.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/304:35 pm
PHL
-
MDW
1 stop6h 27m
Frontier
Sun 6/76:00 am
MDW
-
PHL
1 stop5h 25m
Frontier
Deal found 4/13$187
This Priceline deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:12 pm
PHL
-
ORD
1 stop7h 12m
Multiple Airlines
Mon 4/272:20 pm
ORD
-
PHL
Nonstop2h 14m
Multiple Airlines
Deal found 4/13$188
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:00 pm
PHL
-
MDW
2 stops11h 02m
Multiple Airlines
Mon 5/114:52 pm
MDW
-
PHL
1 stop24h 48m
Multiple Airlines
Deal found 4/14$188
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:12 pm
PHL
-
ORD
1 stop16h 24m
Multiple Airlines
Mon 5/44:28 pm
ORD
-
PHL
2 stops12h 06m
Multiple Airlines
Deal found 4/13$189
This CheapOair deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:44 pm
PHL
-
ORD
1 stop27h 31m
Spirit Airlines
Mon 6/17:33 pm
ORD
-
PHL
1 stop26h 59m
Spirit Airlines
Deal found 4/13$190
This Frontier deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:06 pm
PHL
-
ORD
Nonstop2h 38m
Frontier
Sun 5/178:39 am
ORD
-
PHL
1 stop9h 01m
Frontier
Deal found 4/13$191

Find flight deals from Philadelphia to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Philadelphia (PHL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$184
(Frontier)

One-way from

$89
(Frontier)

Popular in

March

Cheapest in

January

Average price

$288

Good round-trip deal

$296 or less

Good one-way deal

$175 or less
Provider with most accurate pricing for Philadelphia-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Philadelphia-Chicago (CHI) flights.
Search Deals
From Philadelphia to Chicago (CHI)
Search Deals
One-way flight from Philadelphia to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($61 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Philadelphia to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Philadelphia to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Philadelphia to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 17, 2026.
Use the filters below to find and compare flights from Philadelphia to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 6/23

10:40 am-4:16 pm

1 stop6h 36m

Chicago Midway

Fri 6/26

5:11 pm-12:59 am

1 stop6h 48m

$206

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 5/18

4:06 pm-9:09 pm

1 stop6h 03m

Chicago Midway

Tue 5/26

6:23 am-3:00 pm

1 stop7h 37m

$262

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 5/1

3:42 pm-10:28 pm

1 stop7h 46m

Chicago Midway

Thu 5/21

6:23 am-3:00 pm

1 stop7h 37m

$262

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Sat 5/30

6:15 am-3:30 pm

2 stops10h 15m

Chicago O'Hare Intl

Tue 6/2

2:40 pm-10:00 pm

1 stop6h 20m

$272
Quickest round-trip

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 5/6

5:45 pm-6:55 pm

Nonstop2h 10m

Chicago Midway

Mon 5/11

7:40 am-10:35 am

Nonstop1h 55m

$277

PhiladelphiaChicago

PHL - RFD

PHLRFD

Philadelphia

Thu 5/28

9:12 pm-7:45 am

1 stop11h 33m

Chicago Greater Rockford

Sun 5/31

11:27 am-11:58 pm

1 stop11h 31m

$287

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 5/7

5:25 pm-12:15 am

1 stop7h 50m

Chicago Midway

Mon 5/11

6:45 pm-9:45 pm

Nonstop2h 00m

$287

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Tue 7/28

9:21 am-10:50 am

Nonstop2h 29m

Chicago O'Hare Intl

Fri 7/31

6:35 am-9:39 am

Nonstop2h 04m

$291

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Sat 7/4

6:00 am-7:27 am

Nonstop2h 27m

Chicago O'Hare Intl

Mon 7/6

6:04 pm-9:24 pm

Nonstop2h 20m

$291

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Mon 6/22

6:45 pm-8:18 pm

Nonstop2h 33m

Chicago O'Hare Intl

Wed 6/24

9:33 pm-12:45 am

Nonstop2h 12m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/12

Showing 1-10 of 60 resultsSorted by cheapest first
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Compare providers for flights from Philadelphia to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Philadelphia to Chicago in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 stars
Super.comPrice Accuracy-Trust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
CheapOairPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
BudgetAirPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Philadelphia-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Philadelphia-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Philadelphia-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Philadelphia-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Philadelphia-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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 April 10, 2026.

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 56 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, February is the cheapest month in which you can book a flight from Philadelphia to Chicago (average of $40). Flying from Philadelphia to Chicago in January is currently the most expensive (average of $925). 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 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 April 17, 2026.

It’s optimal to fly from Philadelphia to Chicago in the evening. By choosing this option you can save up to 30% on the cost of your flight, compared to a flight at noon.

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 April 11, 2026.

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

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 April 17, 2026.

The most flights from PHL to CHI are scheduled on a Thursday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 on average).

How much does it cost to fly round-trip from Philadelphia to Chicago?

How often are flights from Philadelphia to Chicago delayed?

About 18% of weekly flights between Philadelphia and Chicago have experienced delays in the past year, with the average delay time being 145 minutes.

What is the most punctual flight time for Philadelphia to Chicago flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Philadelphia to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.

The best insider tips for Philadelphia to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Philadelphia to Chicago trip
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Mark Chesnut

Mark Chesnut

Expert on PHL

Mark Chesnut is a travel writer and public speaker with more than 30 years of experience. The 2019 winner of the NLGJA Excellence in Travel Writing Award, Mark is the author of the book “Prepare for Departure” and has covered air travel for multiple top consumer and trade media outlets.

Read more

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated April 17, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican 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.
Southwest
8.0
Very good
4,328 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,328 reviews
Southwest
8.0
Very good
4,328 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,602 reviews
Southwest
8.0
Very good
4,328 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,593 reviews
Southwest
8.0
Very good
4,328 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,986 reviews
Southwest
8.0
Very good
4,328 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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?

    Most people fly from Philadelphia (PHL) if they book a flight from Philadelphia to Chicago. On average, Philadelphia has 37 outbound flights to Chicago per day from 5 airlines. Philadelphia is conveniently located just 7.0 mi from Philadelphia’s city center.

  • How long is the flight from Philadelphia to Chicago?

    Departing from Philadelphia to Chicago will take you 2h 29m. There are 676 mi between Philadelphia and Chicago. This flight may include one or multiple stops.

  • 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 $77 on this airline. Additional options worth looking into are Delta and United Airlines, starting at $98 and $156 round-trip. You may be able to fly from Philadelphia to Chicago for 70% 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 $49. However, be on the lookout for offers from United Airlines and American Airlines, as they are both options that can get you from Philadelphia to Chicago for a low price.

  • 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 most reliable airlines from Philadelphia to Chicago?

    The top 3 most reliable airlines when flying from Philadelphia to Chicago are Air Canada (80%), SWISS (80%) and ANA (79%).

  • What are the cheapest flights from Philadelphia to Chicago?

    The cheapest flight price from Philadelphia to Chicago is $108. On average you can expect to pay $759. The most popular route, (Philadelphia - Chicago O'Hare Intl), can usually be booked for $126.

  • 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.

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

    Currently, February is the cheapest month in which you can book a flight from Philadelphia to Chicago (average of $40). Flying from Philadelphia to Chicago in January is currently the most expensive (average of $925). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Philadelphia to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
LaGuardia to Midway flights
John F Kennedy Intl to Midway flights
Newark to Midway flights
Dulles Intl to Midway flights
Reagan-National to Midway flights
Philadelphia to Midway flights
Newark to St. Louis flights
LaGuardia to St. Louis flights
John F Kennedy Intl to St. Louis flights
Dulles Intl to St. Louis flights
Pittsburgh to O'Hare Intl flights
Reagan-National to St. Louis flights
Philadelphia to St. Louis flights
Allentown to O'Hare Intl flights
Harrisburg to O'Hare Intl flights
Scranton to O'Hare Intl flights
Pittsburgh to Midway flights
Allentown to Midway flights
Pittsburgh to St. Louis flights
State College to O'Hare Intl flights
Harrisburg to Midway flights
Harrisburg to St. Louis flights
Newark to Moline flights
Newark to Bloomington flights
John F Kennedy Intl to Bloomington flights
John F Kennedy Intl to Moline flights
Allentown to St. Louis flights
LaGuardia to Moline flights
Reagan-National to Peoria flights
LaGuardia to Paducah flights
Pittsburgh to Rockford flights
Dulles Intl to Moline flights
Dulles Intl to Peoria flights
Philadelphia to Rockford flights
Newark to Rockford flights
LaGuardia to Peoria flights
Scranton to St. Louis flights
Newark to Peoria flights
State College to St. Louis flights
Pittsburgh to Moline flights

Top 5 airlines flying from Philadelphia to Chicago

Discover the top 5 airlines that operate flights from Philadelphia to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$172FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$266FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$156Average$392FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$158Average$312FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$161Average$308FlexibilityNo cancel feeOn-time71%

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