Chicago

$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 7/26. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Jun 23 — Jun 301
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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 18, 2025.

Round-trip from

$168
(United Airlines)

One-way from

$88
(Booking.com)

Popular in

March

Cheapest in

September

Average price

$213

Good round-trip deal

$220 or less

Good one-way deal

$113 or less
From Philadelphia to Chicago (CHI)
One-way flight from Philadelphia to Chicago (CHI)
Highest demand for flights based on searches. 24% potential increase in price ($74 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
Average for round-trip flights in June 2025
Price to beat on a round-trip flight from Philadelphia to Chicago (CHI).
Price to beat on a one-way flight from Philadelphia to Chicago (CHI).

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 18, 2025.

This United Airlines deal was found by Cheapflights users on 6/17. 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.
Wed 8/66:30 amPHL - ORD
Nonstop2h 24mUnited Airlines
Sun 8/109:23 pmORD - PHL
Nonstop2h 07mUnited Airlines
Deal found 6/17$168
This Southwest deal was found by Cheapflights users on 6/17. 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 8/61:40 pmPHL - MDW
Nonstop2h 05mSouthwest
Sun 8/108:50 amMDW - PHL
Nonstop2h 00mSouthwest
Deal found 6/17$168
This SmartFares deal was found by Cheapflights users on 6/16. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/115:48 pmPHL - ORD
Nonstop2h 39mFrontier
Mon 7/148:27 pmORD - PHL
Nonstop2h 26mFrontier
Deal found 6/16$169
This FlightHub deal was found by Cheapflights users on 6/17. 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 9/108:50 pmPHL - ORD
1 stop26h 38mSpirit Airlines
Fri 9/126:00 amORD - PHL
1 stop25h 05mSpirit Airlines
Deal found 6/17$174
This Cheapflightsfares deal was found by Cheapflights users on 6/18. 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.
Fri 6/2710:38 pmPHL - MDW
Nonstop2h 13mFrontier
Mon 6/306:40 pmMDW - PHL
Nonstop2h 03mFrontier
Deal found 6/18$175
This American Airlines deal was found by Cheapflights users on 6/18. 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 7/289:15 pmPHL - ORD
Nonstop2h 36mAmerican Airlines
Wed 8/68:40 amORD - PHL
Nonstop2h 04mAmerican Airlines
Deal found 6/18$178
This FlightHub deal was found by Cheapflights users on 6/17. 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.
Thu 6/265:45 amPHL - ORD
Nonstop2h 32mMultiple Airlines
Sat 6/2810:43 amORD - PHL
1 stop5h 29mMultiple Airlines
Deal found 6/17$185
This Delta deal was found by Cheapflights users on 6/18. 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 8/2012:47 pmPHL - ORD
1 stop4h 26mDelta
Sat 8/305:30 pmORD - PHL
1 stop5h 21mDelta
Deal found 6/18$197
This Delta deal was found by Cheapflights users on 6/18. 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 8/206:30 amPHL - MDW
1 stop6h 18mDelta
Mon 8/256:17 pmMDW - PHL
1 stop3h 50mDelta
Deal found 6/18$197
This eDestinos deal was found by Cheapflights users on 6/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2310:38 pmPHL - MDW
Nonstop2h 13mMultiple Airlines
Fri 7/118:03 amMDW - PHL
1 stop8h 14mMultiple Airlines
Deal found 6/16$234
This Mytrip deal was found by Cheapflights users on 6/17. 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.
Sat 8/25:21 pmPHL - RFD
2 stops16h 10mMultiple Airlines
Thu 8/79:21 amRFD - PHL
2 stops13h 00mMultiple Airlines
Deal found 6/17$266
This Southwest deal was found by Cheapflights users on 6/17. 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 7/285:30 amPHL - ORD
2 stops10h 30mSouthwest
Mon 7/284:00 pmORD - PHL
1 stop6h 30mSouthwest
Deal found 6/17$292

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 18, 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

Wed 8/6

6:30 am-7:54 am

Nonstop2h 24m

Chicago O'Hare Intl

Sun 8/10

9:23 pm-12:30 am

Nonstop2h 07m

$168

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 8/6

1:40 pm-2:45 pm

Nonstop2h 05m

Chicago Midway

Sun 8/10

8:50 am-11:50 am

Nonstop2h 00m

$168

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Fri 7/11

5:48 pm-7:27 pm

Nonstop2h 39m

Chicago O'Hare Intl

Mon 7/14

8:27 pm-11:53 pm

Nonstop2h 26m

$169

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 9/10

8:50 pm-10:28 pm

1 stop26h 38m

Chicago O'Hare Intl

Fri 9/12

6:00 am-8:05 am

1 stop25h 05m

$174

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 6/27

10:38 pm-11:51 pm

Nonstop2h 13m

Chicago Midway

Mon 6/30

6:40 pm-9:43 pm

Nonstop2h 03m

$175

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Mon 7/28

9:15 pm-10:51 pm

Nonstop2h 36m

Chicago O'Hare Intl

Wed 8/6

8:40 am-11:44 am

Nonstop2h 04m

$178

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Thu 7/3

5:45 am-7:17 am

Nonstop2h 32m

Chicago O'Hare Intl

Tue 7/8

7:49 pm-8:04 am

1 stop11h 15m

$185

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 8/20

12:47 pm-4:13 pm

1 stop4h 26m

Chicago O'Hare Intl

Sat 8/30

5:30 pm-11:51 pm

1 stop5h 21m

$197

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 8/20

5:25 am-9:16 am

1 stop4h 51m

Chicago Midway

Sun 8/31

6:00 am-1:30 pm

1 stop6h 30m

$197

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 6/23

10:38 pm-11:51 pm

Nonstop2h 13m

Chicago Midway

Fri 7/11

8:03 am-5:17 pm

1 stop8h 14m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 26 results
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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.

Southwest

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


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

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 13, 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 18, 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 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 June 15, 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 18, 2025.

The most flights from PHL to CHI are scheduled on a Monday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (22 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 18, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta 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.

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
8.0
Very good

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 United Airlines. Our recent data shows that you can find tickets from as low as $168 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 Spirit Airlines, with whom users have recently found tickets for as low as $88. However, be on the lookout for offers from Frontier and United 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?

  • 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 cheapest flights from Philadelphia to Chicago?

    The cheapest flight price from Philadelphia to Chicago is $84. On average you can expect to pay $848. The most popular route, (Philadelphia - Chicago O'Hare Intl), can usually be booked for $139.

  • 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.

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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$50Average$132FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$294FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$144Average$295FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$154Average$290FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$169Average$305FlexibilityNo cancel feeOn-time63%

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