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$95+ 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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Jul 23 — Jul 301
Thu 7/23
Thu 7/30
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 June 23, 2026.

This Flysmarter deal was found by Cheapflights users on 6/20. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:59 am
JFK
-
ORD
Nonstop2h 48m
JetBlue
Wed 8/126:30 pm
ORD
-
JFK
Nonstop2h 36m
JetBlue
Deal found 6/20$186
This American Airlines deal was found by Cheapflights users on 6/19. 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.
Sat 8/229:46 pm
LGA
-
ORD
Nonstop2h 56m
American Airlines
Wed 8/263:04 pm
ORD
-
LGA
Nonstop2h 18m
American Airlines
Deal found 6/19$186
This JetBlue deal was found by Cheapflights users on 6/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:05 am
JFK
-
ORD
Nonstop2h 45m
JetBlue
Wed 7/226:00 am
ORD
-
JFK
Nonstop2h 17m
JetBlue
Deal found 6/19$187
This United Airlines deal was found by Cheapflights users on 6/21. 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.
Sat 7/186:10 am
LGA
-
ORD
Nonstop2h 39m
United Airlines
Tue 7/219:00 am
ORD
-
LGA
Nonstop2h 23m
United Airlines
Deal found 6/21$187
This Southwest deal was found by Cheapflights users on 6/22. 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 7/229:30 pm
LGA
-
MDW
Nonstop2h 30m
Southwest
Sat 7/255:25 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 6/22$187
This JetBlue deal was found by Cheapflights users on 6/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:05 am
JFK
-
ORD
Nonstop2h 45m
JetBlue
Wed 7/156:00 am
ORD
-
JFK
Nonstop2h 17m
JetBlue
Deal found 6/21$188
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Tue 8/49:29 pm
LGA
-
ORD
Nonstop3h 01m
American Airlines
Sat 8/86:57 pm
ORD
-
LGA
Nonstop2h 20m
American Airlines
Deal found 6/21$188
This Cheapflightsfares deal was found by Cheapflights users on 6/21. 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 8/198:00 pm
JFK
-
ORD
Nonstop2h 58m
JetBlue
Thu 8/206:00 am
ORD
-
JFK
Nonstop2h 17m
JetBlue
Deal found 6/21$189
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:00 am
JFK
-
ORD
Nonstop2h 47m
JetBlue
Mon 10/51:00 pm
ORD
-
JFK
Nonstop2h 20m
JetBlue
Deal found 6/18$191
This Delta deal was found by Cheapflights users on 6/23. 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 9/307:35 pm
JFK
-
ORD
Nonstop3h 02m
Delta
Sun 10/46:00 am
ORD
-
JFK
Nonstop2h 21m
Delta
Deal found 6/23$192
This United Airlines deal was found by Cheapflights users on 6/22. 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.
Fri 9/189:27 pm
LGA
-
ORD
Nonstop2h 32m
United Airlines
Sat 9/192:00 pm
ORD
-
LGA
Nonstop2h 25m
United Airlines
Deal found 6/22$192
This Southwest deal was found by Cheapflights users on 6/23. 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.
Sat 9/197:35 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Wed 9/235:10 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 6/23$192

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 June 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$186
(Flysmarter)

One-way from

$95
(JetBlue)

Popular in

June

Cheapest in

January

Average price

$348

Good round-trip deal

$290 or less

Good one-way deal

$147 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. 14% potential increase in price ($48 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 June 2026
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 June 23, 2026.
Use the filters below to find and compare flights from Pennsylvania to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 9/8

3:01 pm-4:59 pm

Nonstop2h 58m

Chicago O'Hare Intl

Sat 9/12

6:00 pm-9:43 pm

Nonstop2h 43m

$187

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 9/12

3:01 pm-4:59 pm

Nonstop2h 58m

Chicago O'Hare Intl

Tue 9/15

1:55 pm-5:23 pm

Nonstop2h 28m

$187

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 7/14

6:50 pm-8:56 pm

Nonstop3h 06m

Chicago O'Hare Intl

Tue 7/21

8:10 pm-11:44 pm

Nonstop2h 34m

$187

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 7/15

4:00 pm-6:03 pm

Nonstop3h 03m

Chicago O'Hare Intl

Sat 7/18

7:00 am-10:14 am

Nonstop2h 14m

$187

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 10/16

9:27 pm-10:59 pm

Nonstop2h 32m

Chicago O'Hare Intl

Tue 10/20

3:00 pm-6:25 pm

Nonstop2h 25m

$192

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sun 10/4

7:23 am-9:00 am

Nonstop2h 37m

Chicago O'Hare Intl

Wed 10/7

12:00 pm-3:15 pm

Nonstop2h 15m

$192

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 7/22

8:00 pm-9:58 pm

Nonstop2h 58m

Chicago O'Hare Intl

Fri 8/7

6:00 am-9:17 am

Nonstop2h 17m

$197

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 7/17

9:25 pm-10:58 pm

Nonstop2h 33m

Chicago O'Hare Intl

Tue 8/4

6:29 pm-9:58 pm

Nonstop2h 29m

$197

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 7/22

6:05 am-9:36 am

1 stop4h 31m

Chicago O'Hare Intl

Sat 7/25

7:45 pm-11:15 pm

Nonstop2h 30m

$197

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 8/12

6:00 am-9:38 am

1 stop4h 38m

Chicago O'Hare Intl

Tue 8/18

3:00 pm-6:25 pm

Nonstop2h 25m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/23

Showing 1-10 of 60 resultsSorted by cheapest first
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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 $208). Flying from Pennsylvania to Chicago in February is currently the most expensive (average of $391). 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 June 23, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 18% on flights from Pennsylvania to Chicago by exploring options for tickets at noon.

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 June 23, 2026.

The most flights from USPA to CHI are scheduled on a Tuesday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 on average).

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

How far ahead should I book a flight from Pennsylvania to Chicago?

The best time to book flights from Pennsylvania to Chicago is 29 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 June 20, 2026.

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

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 $192, Delta can have you in Chicago from Pennsylvania in 2h 32m. Airlines will cover a distance of 731 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 Frontier and American Airlines, with prices starting from $39 and $48, respectively.

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

    When deciding which route to take from Pennsylvania to Chicago consider Newark - Chicago O'Hare Intl, New York John F Kennedy Intl - 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 Republic Airways (100%), Air Canada (92%) or Copa Airlines (91%) 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 $688 for a flight from Pennsylvania to Chicago. The cheapest flight overall is $94 while the most popular route, (Newark - Chicago O'Hare Intl) is currently priced at $187.

  • 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 $208). Flying from Pennsylvania to Chicago in February is currently the most expensive (average of $391). 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
Benton Harbor
Lansing
Merrillville
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.
Newark to O'Hare Intl flights
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
Dallas/Fort Worth to Midway flights
San Francisco to O'Hare Intl flights
Hobby to O'Hare Intl flights
Seattle to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Newark to Midway flights
Reagan-National to O'Hare Intl flights
Denver to O'Hare Intl flights
Ontario to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Boston to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Orlando to O'Hare Intl flights
Atlanta to O'Hare Intl flights
San Diego to O'Hare Intl flights
Tampa to O'Hare Intl flights
Atlanta to Midway flights
Los Angeles to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Austin to O'Hare Intl flights
LaGuardia to Midway flights
Baltimore to Midway flights
Raleigh to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Dulles Intl to Midway flights
Miami to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
John F Kennedy Intl to Midway flights
San Francisco to Midway flights
Portland to O'Hare Intl flights
Hartford to O'Hare Intl flights
Hobby to Midway flights
San Jose to O'Hare Intl flights
New Orleans to O'Hare Intl flights
Minneapolis to Midway flights
Minneapolis to O'Hare Intl flights
Sky Harbor Intl to Midway flights
Newark to St. Louis flights
Philadelphia to Midway flights
George Bush Intcntl to Midway flights
Las Vegas to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Reagan-National to Midway flights

Top 5 airlines flying from Pennsylvania to Chicago

Discover the top 5 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 June 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$175FlexibilityNo cancel feeOn-time62%
DeltaCheapest$83Average$337FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$91Average$335FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$121Average$341FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$137Average$358FlexibilityNo cancel feeOn-time69%

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