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$88+ 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Philadelphia to Chicago are usually found in September or August, booked 89 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap 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 June 12, 2025.

Round-trip from

$167
(American Airlines)

One-way from

$88
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$207

Good round-trip deal

$213 or less

Good one-way deal

$130 or less
From Philadelphia to Chicago (CHI)
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One-way flight from Philadelphia to Chicago (CHI)
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Highest demand for flights based on searches. 24% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Philadelphia to Chicago (CHI).
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Price to beat on a one-way flight from Philadelphia to Chicago (CHI).
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Find 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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/259:15 pmPHL - ORD
Nonstop2h 34mAmerican Airlines
Mon 9/15:00 amORD - PHL
Nonstop2h 03mAmerican Airlines
Deal found 6/10$167
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/66:30 amPHL - MDW
Nonstop2h 00mSouthwest
Sun 8/108:50 amMDW - PHL
Nonstop2h 00mSouthwest
Deal found 6/10$168
This FlightHub deal was found by Cheapflights users on 6/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/410:38 pmPHL - MDW
Nonstop2h 13mFrontier
Fri 7/116:40 pmMDW - PHL
Nonstop2h 05mFrontier
Deal found 6/11$169
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 9/127:10 pmPHL - ORD
1 stop6h 00mFrontier
Sun 9/146:20 amORD - PHL
Nonstop2h 06mFrontier
Deal found 6/10$173
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/76:30 amPHL - ORD
Nonstop2h 24mUnited Airlines
Sun 8/109:23 pmORD - PHL
Nonstop2h 07mUnited Airlines
Deal found 6/10$177
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 7/45:48 pmPHL - ORD
Nonstop2h 29mMultiple Airlines
Wed 7/95:05 amORD - PHL
1 stop10h 11mMultiple Airlines
Deal found 6/11$182
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/246:00 amPHL - ORD
1 stop4h 25mDelta
Wed 10/13:35 pmORD - PHL
1 stop7h 48mDelta
Deal found 6/10$197
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/84:05 pmPHL - MDW
1 stop6h 37mDelta
Mon 8/111:08 pmMDW - PHL
1 stop5h 10mDelta
Deal found 6/12$198
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/257:10 amPHL - ORD
1 stop7h 55mSouthwest
Sat 8/302:55 pmORD - PHL
1 stop4h 30mSouthwest
Deal found 6/10$210
This FlightHub deal was found by Cheapflights users on 6/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/275:45 amPHL - ORD
1 stop17h 43mSpirit Airlines
Tue 9/26:00 amORD - PHL
1 stop15h 42mSpirit Airlines
Deal found 6/11$224
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/252:24 pmPHL - RFD
1 stop25h 01mMultiple Airlines
Sun 9/288:37 pmRFD - PHL
1 stop31h 55mMultiple Airlines
Deal found 6/11$252
This JetBlue deal was found by Cheapflights users on 6/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1110:20 amPHL - ORD
1 stop8h 35mJetBlue
Sun 9/149:42 amORD - PHL
1 stop7h 03mJetBlue
Deal found 6/9$284

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 June 12, 2025.
Use the filters below to find and compare flights from Philadelphia to Chicago that are best for you.

Fly from

Philadelphia

Fly to

Chicago

Route

Depart

Return

Price

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Mon 8/25

9:15 pm-10:49 pm

Nonstop2h 34m

Chicago O'Hare Intl

Mon 9/1

5:00 am-8:03 am

Nonstop2h 03m

$167

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 8/6

6:30 am-7:30 am

Nonstop2h 00m

Chicago Midway

Sun 8/10

8:50 am-11:50 am

Nonstop2h 00m

$168

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 7/4

10:38 pm-11:51 pm

Nonstop2h 13m

Chicago Midway

Fri 7/11

6:40 pm-9:45 pm

Nonstop2h 05m

$169

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Fri 8/15

11:49 am-4:38 pm

1 stop5h 49m

Chicago O'Hare Intl

Sun 8/17

4:26 pm-7:49 pm

Nonstop2h 23m

$173

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Thu 8/7

6:30 am-7:54 am

Nonstop2h 24m

Chicago O'Hare Intl

Sun 8/10

9:23 pm-12:30 am

Nonstop2h 07m

$177

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Fri 7/4

5:48 pm-7:17 pm

Nonstop2h 29m

Chicago O'Hare Intl

Wed 7/9

5:05 am-4:16 pm

1 stop10h 11m

$182

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Sun 8/17

5:25 am-10:04 am

1 stop5h 39m

Chicago O'Hare Intl

Sat 8/23

5:30 pm-11:51 pm

1 stop5h 21m

$197

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 8/8

4:05 pm-9:42 pm

1 stop6h 37m

Chicago Midway

Mon 8/11

1:08 pm-7:18 pm

1 stop5h 10m

$198

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Mon 8/25

7:10 am-2:05 pm

1 stop7h 55m

Chicago O'Hare Intl

Sat 8/30

2:55 pm-8:25 pm

1 stop4h 30m

$210

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 8/27

5:45 am-10:28 pm

1 stop17h 43m

Chicago O'Hare Intl

Tue 9/2

6:00 am-10:42 pm

1 stop15h 42m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 24 results
1
2
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The best insider tips for Philadelphia to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Philadelphia to Chicago trip
Airlines
Frontier

Frontier's UpFront Plus seats guarantee an empty middle seat for added comfort.


Frontier offers Zone 1 boarding with a carry-on purchase or special fare bundle.

Read more about Frontierby Marisa Garcia
United Airlines

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.

Read more about United Airlinesby Harriet Baskas
Southwest

Southwest allows two free checked bags, including oversized items like skis.


Southwest offers free in-flight entertainment streamed to personal devices.

Read more about Southwestby Marisa Garcia
Airports
PHL

For quick access to Center City, use SEPTA's Airport Line. It's efficient and operates from 5:00 a.m. to midnight.

Read more about PHLby Mark Chesnut
ORD

Use the 'L' train for a reliable trip from ORD to downtown Chicago, avoiding traffic delays.

Read more about ORDby Ramsey Qubein
MDW

The Orange Line train from MDW takes less than 30 minutes to reach downtown Chicago.

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

Marisa Garcia

Marisa Garcia

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 Baskas

Harriet Baskas

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

Ramsey Qubein

Ramsey Qubein

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

Mark Chesnut

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

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 June 9, 2025.

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 89 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 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 12, 2025.

It’s optimal to fly from Philadelphia to Chicago in the evening. By choosing this option you can save up to 39% on the cost of your flight, compared to a flight in the morning.

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 8, 2025.

Travelers seeking maximum savings on their Philadelphia to Chicago flight should consider departing on Tuesday 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

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 12, 2025.

The most flights from PHL to CHI are scheduled on a Thursday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

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.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

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).

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 June 12, 2025.
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.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,925 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 38 outbound flights to Chicago per day from 5 airlines. Philadelphia is conveniently located just 7.0 mi from Philadelphia’s city center.

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

    Our cheapest airline available from Philadelphia to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $167 on this airline. Additional options worth looking into are Southwest and Frontier, starting at $168 and $169 round-trip. You may be able to fly from Philadelphia to Chicago for 27% 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 $88. However, be on the lookout for offers from United Airlines and Southwest, 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 ANA (91%), Copa Airlines (89%) and Air Canada (85%).

  • What are the cheapest flights from Philadelphia to Chicago?

    The cheapest flight price from Philadelphia to Chicago is $86. On average you can expect to pay $1,054. The most popular route, (Philadelphia - Chicago O'Hare Intl), can usually be booked for $134.

  • 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, 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.

See more FAQs

Traveling to a place near Philadelphia?

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

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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
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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$50Average$130FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$294FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$144Average$292FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$155Average$289FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$170Average$306FlexibilityNo cancel feeOn-time63%

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