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$70+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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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 September 16, 2025.

Round-trip from

$112
(Kiwi.com)

One-way from

$70
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$177

Good round-trip deal

$171 or less

Good one-way deal

$132 or less
From Pennsylvania to Chicago (CHI)
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One-way flight from Pennsylvania to Chicago (CHI)
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Highest demand for flights based on searches. 17% potential increase in price ($55 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Pennsylvania to Chicago (CHI).
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Price to beat on a one-way flight from Pennsylvania to Chicago (CHI).
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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 September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/234:10 pmPHL - ORD
Nonstop2h 30mFrontier
Sat 10/252:45 pmORD - PHL
Nonstop2h 15mFrontier
Deal found 9/15$112
This CheapOair deal was found by Cheapflights users on 9/15. 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.
Sat 10/117:10 pmPHL - ORD
Nonstop2h 38mFrontier
Fri 10/178:44 amORD - PHL
1 stop15h 23mFrontier
Deal found 9/15$114
This Frontier deal was found by Cheapflights users on 9/15. 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 10/89:14 pmPHL - ORD
1 stop12h 00mFrontier
Thu 10/96:50 pmORD - PHL
Nonstop2h 20mFrontier
Deal found 9/15$115
This Frontier deal was found by Cheapflights users on 9/15. 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 9/2510:21 amPHL - ORD
Nonstop2h 37mFrontier
Thu 9/258:49 pmORD - PHL
1 stop9h 46mFrontier
Deal found 9/15$118
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/77:04 pmPHL - ORD
Nonstop2h 38mFrontier
Sun 11/95:11 amORD - PHL
Nonstop2h 12mFrontier
Deal found 9/16$120
This Frontier deal was found by Cheapflights users on 9/14. 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.
Sun 11/29:23 amPHL - ORD
Nonstop2h 29mFrontier
Fri 11/79:47 pmORD - PHL
Nonstop2h 12mFrontier
Deal found 9/14$121
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 11/138:29 amPHL - ORD
1 stop6h 30mFrontier
Sun 11/165:11 amORD - PHL
Nonstop2h 12mFrontier
Deal found 9/14$122
This Frontier deal was found by Cheapflights users on 9/14. 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 10/316:00 amPHL - ORD
Nonstop2h 26mFrontier
Fri 11/711:53 amORD - PHL
1 stop11h 46mFrontier
Deal found 9/14$123
This Frontier deal was found by Cheapflights users on 9/14. 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 10/306:00 amPHL - ORD
1 stop12h 12mFrontier
Sun 11/25:01 amORD - PHL
Nonstop2h 12mFrontier
Deal found 9/14$124
This Priceline deal was found by Cheapflights users on 9/15. 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.
Fri 10/105:12 pmPHL - ORD
1 stop9h 19mFrontier
Sat 10/112:45 pmORD - PHL
Nonstop2h 15mFrontier
Deal found 9/15$125
This Priceline deal was found by Cheapflights users on 9/13. 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 10/22:07 pmPHL - ORD
1 stop9h 41mMultiple Airlines
Sun 10/56:00 amORD - PHL
Nonstop2h 15mMultiple Airlines
Deal found 9/13$126
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/3011:00 amJFK - ORD
Nonstop2h 45mFrontier
Thu 11/66:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 9/15$127

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 September 16, 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

LGA - ORD

LGAORD

New York LaGuardia

Wed 10/15

3:25 pm-5:02 pm

Nonstop2h 37m

Chicago O'Hare Intl

Wed 10/22

11:00 am-2:19 pm

Nonstop2h 19m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 10/28

9:45 pm-11:10 pm

Nonstop2h 25m

Chicago Midway

Wed 11/5

8:25 am-11:30 am

Nonstop2h 05m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 9/30

3:13 pm-4:51 pm

Nonstop2h 38m

Chicago O'Hare Intl

Thu 10/2

11:13 am-2:18 pm

Nonstop2h 05m

$138

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 2/19

7:40 pm-9:33 pm

Nonstop2h 53m

Chicago O'Hare Intl

Sat 2/21

7:00 am-10:23 am

Nonstop2h 23m

$139

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 11/5

6:00 am-7:25 am

Nonstop2h 25m

Chicago O'Hare Intl

Sat 11/8

2:20 pm-5:29 pm

Nonstop2h 09m

$139

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 1/14

10:10 am-11:38 am

Nonstop2h 28m

Chicago O'Hare Intl

Sat 1/17

2:30 pm-5:34 pm

Nonstop2h 04m

$139

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Sat 11/1

5:07 pm-6:35 pm

Nonstop2h 28m

Chicago O'Hare Intl

Tue 11/4

7:25 am-10:24 am

Nonstop1h 59m

$139

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Sat 12/13

5:07 pm-6:36 pm

Nonstop2h 29m

Chicago O'Hare Intl

Wed 12/17

9:00 am-12:07 pm

Nonstop2h 07m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 12/5

9:55 pm-11:20 pm

Nonstop2h 25m

Chicago Midway

Wed 12/10

7:15 pm-10:20 pm

Nonstop2h 05m

$142

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 11/14

9:15 pm-10:57 pm

Nonstop2h 42m

Chicago O'Hare Intl

Tue 1/13

12:10 pm-3:23 pm

Nonstop2h 13m

$142

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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, August is the cheapest month in which you can book a flight from Pennsylvania to Chicago (average of $245). Flying from Pennsylvania 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 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 September 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Pennsylvania to Chicago as you normally would.

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 September 16, 2025.

The most flights from USPA to CHI are scheduled on a Monday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 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, United Airlines 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?

    $70 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 Frontier, with prices starting from $70 and $78, respectively.

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

    When deciding which route to take from Pennsylvania to Chicago consider New York LaGuardia - Chicago O'Hare Intl, New York John F Kennedy Intl - 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 SWISS (90%), ANA (87%) or Air Canada (74%) 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 $843 for a flight from Pennsylvania to Chicago. The cheapest flight overall is $79 while the most popular route, (New York LaGuardia - Chicago O'Hare Intl) is currently priced at $57.

  • 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, August is the cheapest month in which you can book a flight from Pennsylvania to Chicago (average of $245). Flying from Pennsylvania 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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.
LaGuardia to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
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Dallas/Fort Worth to Midway flights
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LaGuardia to Midway flights
Atlanta to Midway flights
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Dulles Intl to Midway flights
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Austin to O'Hare Intl flights
San Francisco to Midway flights
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Philadelphia to Midway flights
Minneapolis to O'Hare Intl flights
Hobby to Midway flights
Portland to O'Hare Intl flights
Burbank to O'Hare Intl flights
Hobby to O'Hare Intl flights
Providence to O'Hare Intl flights
Seattle to Midway flights
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Miami to O'Hare Intl flights
Hartford to O'Hare Intl flights
Denver to Midway flights
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Love Field to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
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Minneapolis to Midway flights
John F Kennedy Intl to St. Louis flights
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Boston 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$61Average$166FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$185FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$93Average$377FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$311FlexibilityNo cancel feeOn-time63%
DeltaCheapest$118Average$400FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$130Average$377FlexibilityNo cancel feeOn-time69%

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