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$68+ Cheap flights from Pennsylvania 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Nov 18 — Nov 251
Tue 11/18
Tue 11/25
1 adult, Economy
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Find flight deals from Pennsylvania to Chicago

Cheapest flights from Pennsylvania to Chicago
Explore the most affordable flight options available from Pennsylvania to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 19, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/257:10 pmPHL - ORD
Nonstop2h 38mFrontier
Sat 11/15:45 pmORD - PHL
1 stop5h 28mFrontier
Deal found 10/18$105
This CheapOair deal was found by Cheapflights users on 10/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:00 amPHL - ORD
Nonstop2h 26mFrontier
Mon 11/1011:53 amORD - PHL
1 stop11h 46mFrontier
Deal found 10/17$106
This CheapOair deal was found by Cheapflights users on 10/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:00 amPHL - ORD
Nonstop2h 26mFrontier
Mon 11/38:26 amORD - PHL
Nonstop2h 13mFrontier
Deal found 10/18$108
This Frontier deal was found by Cheapflights users on 10/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/257:10 pmPHL - ORD
Nonstop2h 38mFrontier
Mon 10/2711:51 amORD - PHL
Nonstop2h 09mFrontier
Deal found 10/17$109
This Frontier deal was found by Cheapflights users on 10/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:36 pmPHL - ORD
Nonstop2h 30mFrontier
Wed 12/312:15 pmORD - PHL
Nonstop2h 15mFrontier
Deal found 10/18$110
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/29:23 amPHL - ORD
Nonstop2h 29mFrontier
Mon 11/38:26 amORD - PHL
Nonstop2h 13mFrontier
Deal found 10/18$111
This CheapOair deal was found by Cheapflights users on 10/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/234:10 pmPHL - ORD
Nonstop2h 30mFrontier
Thu 10/308:26 amORD - PHL
Nonstop2h 13mFrontier
Deal found 10/17$112
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/257:10 pmPHL - ORD
Nonstop2h 38mFrontier
Sun 10/2611:51 amORD - PHL
Nonstop2h 09mFrontier
Deal found 10/17$113
This CheapOair deal was found by Cheapflights users on 10/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:00 amPHL - ORD
Nonstop2h 26mFrontier
Fri 11/146:00 amORD - PHL
1 stop21h 49mFrontier
Deal found 10/17$114
This Frontier deal was found by Cheapflights users on 10/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2312:59 pmJFK - ORD
1 stop13h 25mFrontier
Mon 10/276:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 10/18$116
This Priceline deal was found by Cheapflights users on 10/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2912:59 pmLGA - ORD
Nonstop2h 46mMultiple Airlines
Sat 11/111:51 amORD - LGA
1 stop6h 08mMultiple Airlines
Deal found 10/18$116
This CheapOair deal was found by Cheapflights users on 10/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:00 amPHL - ORD
Nonstop2h 26mFrontier
Sun 11/211:51 amORD - PHL
1 stop11h 48mFrontier
Deal found 10/18$116

Cheap flight deals from Pennsylvania to Chicago

Keep the following information in mind while searching for Pennsylvania to Chicago flight deals. Data was last updated October 19, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$105
(Kiwi.com)

One-way from

$68
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$228

Good round-trip deal

$160 or less

Good one-way deal

$109 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 Pennsylvania to Chicago (CHI)
Search Deals
One-way flight from Pennsylvania to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Pennsylvania to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Pennsylvania to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pennsylvania 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 October 19, 2025.
Use the filters below to find and compare flights from Pennsylvania to Chicago that are best for you.

Fly from

Pennsylvania

Fly to

Chicago

Route

Depart

Return

Price

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 11/5

7:00 pm-8:52 pm

Nonstop2h 52m

Chicago O'Hare Intl

Wed 11/12

6:45 am-9:59 am

Nonstop2h 14m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 11/5

9:15 pm-10:57 pm

Nonstop2h 42m

Chicago O'Hare Intl

Sat 11/8

2:00 pm-5:08 pm

Nonstop2h 08m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 11/13

9:00 am-10:25 am

Nonstop2h 25m

Chicago Midway

Mon 11/17

7:15 pm-10:20 pm

Nonstop2h 05m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 11/15

7:00 pm-8:52 pm

Nonstop2h 52m

Chicago O'Hare Intl

Thu 11/20

8:20 am-11:35 am

Nonstop2h 15m

$138

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 11/7

8:15 pm-9:57 pm

Nonstop2h 42m

Chicago O'Hare Intl

Mon 11/10

8:00 pm-11:16 pm

Nonstop2h 16m

$138

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 11/5

8:15 am-9:55 am

Nonstop2h 40m

Chicago O'Hare Intl

Sun 11/9

7:00 am-10:07 am

Nonstop2h 07m

$138

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 12/13

8:00 pm-9:52 pm

Nonstop2h 52m

Chicago O'Hare Intl

Thu 1/8

2:05 pm-5:26 pm

Nonstop2h 21m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 11/25

8:30 pm-10:21 pm

Nonstop2h 51m

Chicago O'Hare Intl

Sat 11/29

7:00 am-10:17 am

Nonstop2h 17m

$139

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 10/29

8:15 am-9:55 am

Nonstop2h 40m

Chicago O'Hare Intl

Thu 10/30

8:00 am-11:07 am

Nonstop2h 07m

$139

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 2/16

5:45 am-7:13 am

Nonstop2h 28m

Chicago O'Hare Intl

Mon 2/23

7:05 pm-10:14 pm

Nonstop2h 09m

$140

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/18

Showing 1-10 of 60 results
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Best time to book a flight from Pennsylvania to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Pennsylvania 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 Pennsylvania to Chicago

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

Currently, November is the cheapest month in which you can book a flight from Pennsylvania to Chicago (average of $44). Flying from Pennsylvania to Chicago in June is currently the most expensive (average of $147). 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 PA to CHI?

Find hourly flight availability from Pennsylvania 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 October 19, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 28% on flights from Pennsylvania to Chicago by exploring options for tickets in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Pennsylvania to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Pennsylvania to Chicago flight should consider departing on Friday mornings 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 Pennsylvania to Chicago

Explore weekly flight availability from Pennsylvania 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 October 19, 2025.

The most flights from USPA to CHI are scheduled on a Saturday (47 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (27 on average).

Related info for your journey

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

  • How long is the flight from Pennsylvania to Chicago?

    For as low as $137, JetBlue can have you in Chicago from Pennsylvania in 2h 25m. Airlines will cover a distance of 722 mi. Generally, flights for this route are nonstop.

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

    $69 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Southwest and JetBlue, with prices starting from $69 and $70, respectively.

  • What are the most popular routes from Pennsylvania to Chicago?

    When deciding which route to take from Pennsylvania to Chicago consider New York John F Kennedy Intl - Chicago O'Hare Intl, Newark - Chicago O'Hare Intl or New York LaGuardia - Chicago O'Hare Intl as they are the most popular.

  • What are the most reliable airlines from Pennsylvania to Chicago?

    No one likes to see their flight delayed. When booking a flight from Pennsylvania to Chicago consider choosing ANA (90%), SWISS (89%) or Japan Airlines (82%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Pennsylvania to Chicago?

    On average you can expect to pay $907 for a flight from Pennsylvania to Chicago. The cheapest flight overall is $72 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $54.

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

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

  • How can I find direct flights from Pennsylvania to Chicago?

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

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

    Yes. Cheapflights offers flight deals from Pennsylvania 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 Pennsylvania to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Pennsylvania to Chicago (average of $44). Flying from Pennsylvania to Chicago in June is currently the most expensive (average of $147). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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Alternative routes for Pennsylvania 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
Dallas/Fort Worth to O'Hare Intl flights
Newark to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Boston to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Denver to O'Hare Intl flights
Seattle to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Minneapolis to O'Hare Intl flights
Newark to Midway flights
Ontario to O'Hare Intl flights
Atlanta to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Tampa to O'Hare Intl flights
Dulles Intl to Midway flights
Fort Lauderdale to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
LaGuardia to Midway flights
Love Field to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Baltimore to Midway flights
Hobby to O'Hare Intl flights
Hobby to Midway flights
John F Kennedy Intl to St. Louis flights
Los Angeles to Midway flights
Minneapolis to Midway flights
Denver to Midway flights
Miami to O'Hare Intl flights
Orlando to O'Hare Intl flights
LaGuardia to St. Louis flights
Austin to O'Hare Intl flights
Newark to St. Louis flights
Charlotte to O'Hare Intl flights
Portland to O'Hare Intl flights
San Francisco to Midway flights
Cleveland to O'Hare Intl flights
San Diego to O'Hare Intl flights
Orlando to Midway flights
George Bush Intcntl to O'Hare Intl flights
Seattle to Midway flights
San Jose to O'Hare Intl flights
Hartford to O'Hare Intl flights

Top 6 airlines flying from Pennsylvania to Chicago

Discover the top 6 airlines that operate flights from Pennsylvania 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 October 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$62Average$174FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$185FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$93Average$377FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$312FlexibilityNo cancel feeOn-time63%
DeltaCheapest$118Average$409FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$128Average$377FlexibilityNo cancel feeOn-time69%

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