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$79+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Jul 13 — Jul 201
Sun 7/13
Sun 7/20
1 adult, Economy
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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

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 July 8, 2025.

Round-trip from

$156
(Cheapflightsfares)

One-way from

$79
(United Airlines)

Popular in

March

Cheapest in

September

Average price

$189

Good round-trip deal

$180 or less

Good one-way deal

$96 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 ($73 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 8, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/285:48 pmPHL - ORD
Nonstop2h 39mFrontier
Fri 8/18:27 pmORD - PHL
Nonstop2h 26mFrontier
Deal found 7/8$156
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 8/89:12 pmPHL - ORD
1 stop10h 52mMultiple Airlines
Fri 8/226:35 amORD - PHL
Nonstop2h 17mMultiple Airlines
Deal found 7/8$157
This Southwest deal was found by Cheapflights users on 7/7. 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.
Tue 8/56:30 amPHL - MDW
Nonstop2h 00mSouthwest
Thu 8/77:40 amMDW - PHL
Nonstop1h 55mSouthwest
Deal found 7/7$157
This Cheapflightsfares deal was found by Cheapflights users on 7/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:05 amPHL - MDW
Nonstop2h 15mFrontier
Fri 11/148:15 amMDW - PHL
Nonstop2h 02mFrontier
Deal found 7/7$158
This United Airlines deal was found by Cheapflights users on 7/7. 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.
Tue 8/126:05 amPHL - ORD
1 stop6h 44mUnited Airlines
Sat 8/169:23 pmORD - PHL
Nonstop2h 07mUnited Airlines
Deal found 7/7$159
This American Airlines deal was found by Cheapflights users on 7/6. 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.
Tue 7/299:15 pmPHL - ORD
Nonstop2h 36mAmerican Airlines
Sat 8/28:44 pmORD - PHL
Nonstop2h 24mAmerican Airlines
Deal found 7/6$161
This CheapOair deal was found by Cheapflights users on 7/8. 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.
Mon 8/119:12 pmPHL - ORD
1 stop10h 52mSpirit Airlines
Thu 8/146:56 amORD - PHL
1 stop6h 42mSpirit Airlines
Deal found 7/8$174
This Southwest deal was found by Cheapflights users on 7/6. 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.
Tue 8/53:40 pmPHL - ORD
1 stop6h 50mSouthwest
Tue 8/126:00 amORD - PHL
1 stop7h 30mSouthwest
Deal found 7/6$177
This Delta deal was found by Cheapflights users on 7/7. 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 8/66:00 amPHL - ORD
1 stop5h 16mDelta
Tue 8/122:00 pmORD - PHL
1 stop4h 10mDelta
Deal found 7/7$197
This Delta deal was found by Cheapflights users on 7/7. 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.
Sat 8/29:39 amPHL - MDW
1 stop3h 50mDelta
Sat 8/25:53 pmMDW - PHL
1 stop4h 15mDelta
Deal found 7/7$197
This Mytrip deal was found by Cheapflights users on 7/7. 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 8/219:47 amPHL - RFD
1 stop5h 29mMultiple Airlines
Sun 8/243:06 pmRFD - PHL
2 stops17h 50mMultiple Airlines
Deal found 7/7$205

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 July 8, 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 7/28

5:48 pm-7:27 pm

Nonstop2h 39m

Chicago O'Hare Intl

Fri 8/1

8:27 pm-11:53 pm

Nonstop2h 26m

$156

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 9/26

6:05 am-7:16 am

Nonstop2h 11m

Chicago Midway

Mon 9/29

5:04 pm-12:54 am

1 stop6h 50m

$156

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Fri 8/8

9:12 pm-7:04 am

1 stop10h 52m

Chicago O'Hare Intl

Fri 8/22

6:35 am-9:52 am

Nonstop2h 17m

$157

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Tue 8/5

6:30 am-7:30 am

Nonstop2h 00m

Chicago Midway

Thu 8/7

7:40 am-10:35 am

Nonstop1h 55m

$157

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Tue 8/12

6:05 am-11:49 am

1 stop6h 44m

Chicago O'Hare Intl

Sat 8/16

9:23 pm-12:30 am

Nonstop2h 07m

$159

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Tue 7/29

9:15 pm-10:51 pm

Nonstop2h 36m

Chicago O'Hare Intl

Sat 8/2

8:44 pm-12:08 am

Nonstop2h 24m

$161

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Mon 8/4

9:12 pm-7:04 am

1 stop10h 52m

Chicago O'Hare Intl

Mon 8/11

4:37 pm-8:04 am

2 stops14h 27m

$176

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Tue 8/5

3:40 pm-9:30 pm

1 stop6h 50m

Chicago O'Hare Intl

Tue 8/12

6:00 am-2:30 pm

1 stop7h 30m

$177

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 8/6

6:00 am-10:16 am

1 stop5h 16m

Chicago O'Hare Intl

Tue 8/12

2:00 pm-7:10 pm

1 stop4h 10m

$197

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 8/6

6:00 am-8:44 am

1 stop3h 44m

Chicago Midway

Wed 8/6

1:09 pm-7:29 pm

1 stop5h 20m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/8

Showing 1-10 of 22 results
1
2
3

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
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
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
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 27, 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 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 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 July 8, 2025.

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 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 July 6, 2025.

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

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 July 8, 2025.

The most flights from PHL to CHI are scheduled on a Monday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 on average).

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 July 8, 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
4,256 reviews

Entertainment

7.6

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

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
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.6

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

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
7,958 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.6

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

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
8,844 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.6

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

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
2,910 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.6

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

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
4,256 reviews

Entertainment

7.6

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

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 43 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 Frontier. Our recent data shows that you can find tickets from as low as $156 on this airline. Additional options worth looking into are Southwest and United Airlines, starting at $157 and $159 round-trip. You may be able to fly from Philadelphia to Chicago for 33% 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 United Airlines, with whom users have recently found tickets for as low as $79. However, be on the lookout for offers from Southwest and Spirit 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 ANA (86%), SWISS (82%) and Copa Airlines (75%).

  • 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 $1,169. The most popular route, (Philadelphia - Chicago O'Hare Intl), can usually be booked for $117.

  • 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
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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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LaGuardia to O'Hare Intl flights
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Allentown to Midway flights
State College to O'Hare Intl flights
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Scranton to St. Louis flights
Newark to Moline flights
John F Kennedy Intl to Moline flights
Allentown to St. Louis flights
LaGuardia to Moline flights
Philadelphia to Moline flights
LaGuardia to Evansville flights
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Philadelphia to Peoria flights
State College to St. Louis flights
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Harrisburg to Moline flights
Harrisburg to St. Louis flights
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Newark to Springfield 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 July 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$50Average$139FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$314FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$147Average$305FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$294FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$168Average$300FlexibilityNo cancel feeOn-time63%

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