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$53+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap 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 December 28, 2025.

This Frontier deal was found by Cheapflights users on 12/28. 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.
Tue 12/3011:30 amEWR - MDW
Nonstop2h 31mFrontier
Tue 1/136:30 pmMDW - EWR
Nonstop2h 00mFrontier
Deal found 12/28$113
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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.
Wed 12/3111:00 amJFK - ORD
Nonstop2h 57mFrontier
Wed 1/78:35 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/26$155
This Cheapflightsfares deal was found by Cheapflights users on 12/28. 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.
Wed 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Thu 1/85:53 pmORD - LGA
Nonstop2h 06mSpirit Airlines
Deal found 12/28$155
This Super.com deal was found by Cheapflights users on 12/28. 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.
Wed 12/316:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Wed 1/79:34 amORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 12/28$159
This Kiwi.com deal was found by Cheapflights users on 12/28. 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 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Mon 1/125:53 pmORD - LGA
Nonstop2h 06mSpirit Airlines
Deal found 12/28$162
This Kiwi.com deal was found by Cheapflights users on 12/28. 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 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Sat 1/105:53 pmORD - LGA
Nonstop2h 06mSpirit Airlines
Deal found 12/28$165
This Cheapflightsfares deal was found by Cheapflights users on 12/27. 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.
Tue 12/3011:30 amEWR - MDW
Nonstop2h 31mFrontier
Thu 1/17:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/27$168
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/316:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Tue 1/69:34 amORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 12/26$170
This Super.com deal was found by Cheapflights users on 12/27. 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.
Tue 12/308:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Sat 1/34:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 12/27$170
This Super.com deal was found by Cheapflights users on 12/26. 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.
Wed 12/3111:00 amJFK - ORD
Nonstop2h 57mFrontier
Mon 1/56:40 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/26$171
This Kiwi.com deal was found by Cheapflights users on 12/27. 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 12/308:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Mon 1/125:53 pmORD - LGA
Nonstop2h 06mSpirit Airlines
Deal found 12/27$173
This Frontier deal was found by Cheapflights users on 12/28. 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.
Wed 12/3111:00 amJFK - ORD
Nonstop2h 57mFrontier
Fri 1/98:35 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/28$174

Find flight deals from Pennsylvania to Chicago

Keep the following information in mind while searching for Pennsylvania to Chicago flight deals. Data was last updated December 28, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$89
(Mytrip)

One-way from

$53
(CheapOair)

Popular in

February

Cheapest in

September

Average price

$287

Good round-trip deal

$289 or less

Good one-way deal

$186 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. 12% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 28, 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

Fri 1/16

5:25 pm-7:36 pm

Nonstop3h 11m

Chicago O'Hare Intl

Sun 1/18

9:15 am-12:32 pm

Nonstop2h 17m

$97

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sun 2/22

6:10 am-7:55 am

Nonstop2h 45m

Chicago O'Hare Intl

Fri 2/27

12:05 pm-3:19 pm

Nonstop2h 14m

$97

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 1/30

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Mon 2/2

6:05 am-9:10 am

Nonstop2h 05m

$97

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 1/16

9:21 pm-11:09 pm

Nonstop2h 48m

Chicago O'Hare Intl

Mon 1/19

8:00 am-11:13 am

Nonstop2h 13m

$97

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 2/28

12:59 pm-11:47 pm

1 stop11h 48m

Chicago O'Hare Intl

Mon 3/2

5:58 pm-8:59 pm

Nonstop2h 01m

$98

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 3/19

10:05 pm-11:33 pm

Nonstop2h 28m

Chicago O'Hare Intl

Wed 3/25

5:53 pm-9:00 pm

Nonstop2h 07m

$112

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 4/22

12:59 pm-2:41 pm

Nonstop2h 42m

Chicago O'Hare Intl

Sun 4/26

9:04 am-12:04 pm

Nonstop2h 00m

$113

NewarkChicago

EWR - ORD

EWRORD

Newark

Mon 1/12

5:59 am-11:35 am

1 stop6h 36m

Chicago O'Hare Intl

Thu 1/15

4:38 pm-7:46 pm

Nonstop2h 08m

$117

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 2/23

9:20 pm-11:21 pm

Nonstop3h 01m

Chicago O'Hare Intl

Wed 2/25

6:04 am-9:20 am

Nonstop2h 16m

$117

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 1/15

2:05 pm-3:45 pm

Nonstop2h 40m

Chicago Midway

Mon 1/19

6:05 am-9:10 am

Nonstop2h 05m

$117

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

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, December is the cheapest month in which you can book a flight from Pennsylvania to Chicago (average of $60). Flying from Pennsylvania to Chicago in February is currently the most expensive (average of $148). 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 December 28, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 20% 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 December 28, 2025.

The most flights from USPA to CHI are scheduled on a Sunday (41 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (25 on average).

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

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 $97, JetBlue can have you in Chicago from Pennsylvania in 2h 40m. 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?

    $38 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on American Airlines and Frontier, with prices starting from $48 and $49, 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, New York LaGuardia - Chicago O'Hare Intl or Newark - 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 (80%), Japan Airlines (78%) or Copa Airlines (75%) 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 $1,056 for a flight from Pennsylvania to Chicago. The cheapest flight overall is $69 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $76.

  • 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, December is the cheapest month in which you can book a flight from Pennsylvania to Chicago (average of $60). Flying from Pennsylvania to Chicago in February is currently the most expensive (average of $148). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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.
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
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LaGuardia to O'Hare Intl flights
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San Francisco to O'Hare Intl flights
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Dallas/Fort Worth to Midway flights
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John F Kennedy Intl to Midway flights
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Love Field to O'Hare Intl flights
Minneapolis to Midway flights
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Tampa to O'Hare Intl flights
Los Angeles to Midway flights
George Bush Intcntl to O'Hare Intl flights
Orlando to O'Hare Intl flights
Ontario to O'Hare Intl flights
Dulles Intl to Midway flights
Raleigh to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Miami to O'Hare Intl flights
San Francisco to Midway flights
Hobby to Midway flights
Hobby to O'Hare Intl flights
Boston to Midway flights
San Diego to O'Hare Intl flights
Love Field to Midway flights
Fort Lauderdale to O'Hare Intl flights
Orlando to Midway flights
Detroit to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
George Bush Intcntl to Midway flights
Denver to St. Louis flights
Kansas City to O'Hare Intl flights
Tampa to Midway flights
Columbus to O'Hare Intl flights
Denver to Midway 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$180FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$185FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$91Average$295FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$315FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$104Average$375FlexibilityNo cancel feeOn-time69%
DeltaCheapest$118Average$418FlexibilityNo cancel feeOn-timeN/A

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