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$64+ 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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
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 November 4, 2025.

This Frontier deal was found by Cheapflights users on 11/4. 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.
Fri 12/121:00 pmJFK - ORD
Nonstop2h 57mFrontier
Wed 12/174:01 pmORD - JFK
1 stop7h 58mFrontier
Deal found 11/4$96
This Trip.com deal was found by Cheapflights users on 11/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/138:41 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Mon 12/154:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 11/4$96
This Frontier deal was found by Cheapflights users on 11/4. 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.
Fri 11/1411:00 amJFK - ORD
Nonstop2h 45mFrontier
Tue 11/1812:37 pmORD - JFK
1 stop10h 56mFrontier
Deal found 11/4$97
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Thu 11/2012:59 pmLGA - ORD
Nonstop2h 32mSpirit Airlines
Thu 12/184:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 11/3$97
This Priceline deal was found by Cheapflights users on 11/4. 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.
Mon 11/1711:00 amJFK - ORD
Nonstop2h 45mFrontier
Tue 11/186:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 11/4$98
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 11/104:59 pmLGA - ORD
Nonstop2h 35mSpirit Airlines
Thu 11/137:34 pmORD - LGA
Nonstop2h 08mSpirit Airlines
Deal found 11/4$98
This Frontier deal was found by Cheapflights users on 11/4. 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 12/31:00 pmJFK - ORD
Nonstop2h 57mFrontier
Sat 12/68:36 amORD - JFK
Nonstop2h 24mFrontier
Deal found 11/4$99
This Priceline deal was found by Cheapflights users on 11/4. 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.
Sat 11/158:59 amLGA - ORD
Nonstop2h 31mMultiple Airlines
Wed 11/1912:37 pmORD - LGA
1 stop5h 52mMultiple Airlines
Deal found 11/4$99
This Priceline deal was found by Cheapflights users on 11/4. 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.
Thu 12/410:00 amJFK - ORD
1 stop8h 27mFrontier
Sat 12/68:36 amORD - JFK
Nonstop2h 24mFrontier
Deal found 11/4$100
This Spirit deal was found by Cheapflights users on 11/4. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:59 pmLGA - ORD
Nonstop2h 32mSpirit Airlines
Sun 12/74:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 11/4$100
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/2212:59 pmLGA - ORD
Nonstop2h 32mSpirit Airlines
Sat 12/134:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 11/3$101
This Flightnetwork deal was found by Cheapflights users on 11/4. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/31:00 pmJFK - ORD
Nonstop2h 57mFrontier
Sun 12/72:36 pmORD - JFK
1 stop18h 24mFrontier
Deal found 11/4$102

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 November 4, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$96
(Frontier)

One-way from

$64
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$198

Good round-trip deal

$149 or less

Good one-way deal

$142 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 November 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 November 4, 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

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 1/8

1:00 pm-11:25 pm

1 stop11h 25m

Chicago Midway

Mon 1/12

3:52 pm-12:50 am

1 stop7h 58m

$110

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 12/13

6:00 am-10:30 pm

1 stop17h 30m

Chicago Midway

Tue 12/16

2:49 pm-12:59 am

1 stop9h 10m

$117

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sun 12/14

6:00 am-10:30 pm

1 stop17h 30m

Chicago Midway

Mon 12/15

8:42 pm-12:00 pm

1 stop14h 18m

$132

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 12/2

8:01 am-9:56 am

Nonstop2h 55m

Chicago O'Hare Intl

Wed 12/10

6:30 pm-10:04 pm

Nonstop2h 34m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 12/10

8:00 pm-9:52 pm

Nonstop2h 52m

Chicago O'Hare Intl

Tue 12/16

7:00 am-10:17 am

Nonstop2h 17m

$137

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 12/6

6:20 pm-8:07 pm

Nonstop2h 47m

Chicago O'Hare Intl

Mon 12/8

9:08 pm-12:13 am

Nonstop2h 05m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 12/6

8:35 am-10:00 am

Nonstop2h 25m

Chicago Midway

Mon 12/8

7:15 pm-10:20 pm

Nonstop2h 05m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 2/19

8:10 am-9:56 am

Nonstop2h 46m

Chicago O'Hare Intl

Sat 2/21

7:01 am-10:38 am

Nonstop2h 37m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 12/9

6:00 am-7:30 am

Nonstop2h 30m

Chicago Midway

Tue 12/9

5:55 pm-9:00 pm

Nonstop2h 05m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 11/19

8:00 am-9:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Wed 11/19

6:33 pm-10:05 pm

Nonstop2h 32m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

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 November 4, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 22% 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 November 4, 2025.

The most flights from USPA to CHI are scheduled on a Monday (49 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 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 $137, Frontier can have you in Chicago from Pennsylvania in 2h 47m. Airlines will cover a distance of 716 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $68 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Delta and JetBlue, with prices starting from $69 and $69, 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%), Copa Airlines (87%) or SWISS (85%) 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 $873 for a flight from Pennsylvania to Chicago. The cheapest flight overall is $70 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $98.

  • 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
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Hammond
Porter
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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.
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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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$61Average$176FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$185FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$92Average$297FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$320FlexibilityNo cancel feeOn-time63%
DeltaCheapest$118Average$411FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$126Average$370FlexibilityNo cancel feeOn-time69%

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