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$87+ 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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Jun 14 — Jun 211
Sun 6/14
Sun 6/21
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 May 15, 2026.

This SmartFares deal was found by Cheapflights users on 5/12. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/47:00 am
JFK
-
ORD
Nonstop2h 45m
JetBlue
Sun 7/56:00 am
ORD
-
JFK
Nonstop2h 20m
JetBlue
Deal found 5/12$173
This SmartFares deal was found by Cheapflights users on 5/11. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/57:00 am
JFK
-
ORD
Nonstop2h 45m
JetBlue
Tue 7/149:39 am
ORD
-
JFK
Nonstop2h 16m
JetBlue
Deal found 5/11$176
This Delta deal was found by Cheapflights users on 5/12. 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.
Sat 7/187:35 pm
JFK
-
ORD
Nonstop3h 17m
Delta
Wed 7/221:00 pm
ORD
-
JFK
Nonstop2h 33m
Delta
Deal found 5/12$177
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Wed 6/177:00 am
LGA
-
ORD
Nonstop2h 29m
United Airlines
Sat 6/207:50 pm
ORD
-
LGA
Nonstop2h 30m
United Airlines
Deal found 5/12$177
This Southwest deal was found by Cheapflights users on 5/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:00 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Tue 6/237:45 pm
MDW
-
LGA
Nonstop2h 10m
Southwest
Deal found 5/13$177
This American Airlines deal was found by Cheapflights users on 5/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/161:59 pm
JFK
-
ORD
Nonstop2h 56m
American Airlines
Sat 6/204:44 pm
ORD
-
JFK
Nonstop2h 31m
American Airlines
Deal found 5/14$178
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Wed 6/176:25 am
LGA
-
ORD
Nonstop2h 43m
American Airlines
Sat 6/276:20 pm
ORD
-
LGA
Nonstop2h 16m
American Airlines
Deal found 5/12$178
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Wed 6/176:25 am
LGA
-
ORD
Nonstop2h 43m
American Airlines
Sat 6/205:59 am
ORD
-
LGA
Nonstop2h 16m
American Airlines
Deal found 5/12$179
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 6/25:55 am
EWR
-
MDW
1 stop6h 17m
Frontier
Tue 6/96:00 am
MDW
-
EWR
1 stop14h 29m
Frontier
Deal found 5/10$180
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Mon 8/176:00 am
LGA
-
ORD
Nonstop2h 44m
American Airlines
Wed 8/1910:05 am
ORD
-
LGA
Nonstop2h 11m
American Airlines
Deal found 5/11$180
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Wed 7/86:56 am
EWR
-
ORD
Nonstop2h 48m
American Airlines
Tue 7/148:09 pm
ORD
-
EWR
Nonstop2h 21m
American Airlines
Deal found 5/12$181
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/56:40 am
LGA
-
ORD
Nonstop2h 46m
American Airlines
Sat 8/16:00 am
ORD
-
LGA
Nonstop2h 16m
American Airlines
Deal found 5/13$181

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 May 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$173
(SmartFares)

One-way from

$87
(Super.com)

Popular in

March

Cheapest in

January

Average price

$307

Good round-trip deal

$294 or less

Good one-way deal

$149 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. 19% potential increase in price ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 15, 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

LGA - MDW

LGAMDW

New York LaGuardia

Tue 6/30

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Sat 7/4

11:35 am-2:40 pm

Nonstop2h 05m

$177

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 7/10

7:12 pm-9:00 pm

Nonstop2h 48m

Chicago O'Hare Intl

Wed 7/15

9:30 pm-12:53 am

Nonstop2h 23m

$182

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 7/8

7:20 am-9:13 am

Nonstop2h 53m

Chicago O'Hare Intl

Mon 7/13

10:00 am-1:20 pm

Nonstop2h 20m

$187

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 7/22

6:00 am-11:53 am

1 stop6h 53m

Chicago O'Hare Intl

Sat 7/25

7:45 pm-11:15 pm

Nonstop2h 30m

$187

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 6/10

6:00 am-7:41 am

Nonstop2h 41m

Chicago O'Hare Intl

Thu 6/11

6:00 am-9:12 am

Nonstop2h 12m

$187

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 6/17

5:45 pm-10:35 pm

1 stop5h 50m

Chicago Midway

Sat 6/27

5:00 am-8:00 am

Nonstop2h 00m

$187

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 7/28

6:00 am-11:53 am

1 stop6h 53m

Chicago O'Hare Intl

Sat 8/1

4:00 pm-7:22 pm

Nonstop2h 22m

$187

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 7/4

3:00 pm-5:11 pm

Nonstop3h 11m

Chicago O'Hare Intl

Sun 7/5

6:05 am-9:26 am

Nonstop2h 21m

$192

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 8/12

12:05 pm-4:50 pm

1 stop5h 45m

Chicago Midway

Fri 8/14

7:50 pm-10:55 pm

Nonstop2h 05m

$192

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 5/26

12:45 pm-2:30 pm

Nonstop2h 45m

Chicago O'Hare Intl

Fri 5/29

10:45 am-2:17 pm

Nonstop2h 32m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

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

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

The best time to book flights from Pennsylvania to Chicago is 64 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 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 $202). Flying from Pennsylvania to Chicago in February is currently the most expensive (average of $398). 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 May 15, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 15% on flights from Pennsylvania to Chicago by exploring options for tickets at noon.

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 May 9, 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.

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 May 15, 2026.

The most flights from USPA to CHI are scheduled on a Monday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 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 $177, Southwest can have you in Chicago from Pennsylvania in 2h 20m. 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 $45 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 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 Air Canada (86%), Japan Airlines (81%) or ANA (81%) 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 $595 for a flight from Pennsylvania to Chicago. The cheapest flight overall is $85 while the most popular route, (New York LaGuardia - Chicago O'Hare Intl) is currently priced at $177.

  • 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 $202). Flying from Pennsylvania to Chicago in February is currently the most expensive (average of $398). 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.
Dallas/Fort Worth to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Seattle to O'Hare Intl flights
Hobby to O'Hare Intl flights
Newark to Midway flights
Baltimore to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Ontario to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Denver to O'Hare Intl flights
Orlando to O'Hare Intl flights
Boston to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Tampa to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Miami to O'Hare Intl flights
Dulles Intl to Midway flights
Raleigh to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Los Angeles to Midway flights
Santa Ana to O'Hare Intl flights
Austin to O'Hare Intl flights
LaGuardia to Midway flights
San Diego to O'Hare Intl flights
Hobby to Midway flights
Baltimore to Midway flights
Charlotte to O'Hare Intl flights
Atlanta to Midway flights
San Jose to O'Hare Intl flights
Newark to St. Louis flights
Hartford to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Philadelphia to Midway flights
LaGuardia to St. Louis flights
Reagan-National to Midway flights
San Francisco to Midway flights
Orlando to Midway flights
Boston to Midway flights
Portland to O'Hare Intl flights
Denver to Midway flights
Las Vegas to O'Hare Intl flights
Miami 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 May 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$172FlexibilityNo cancel feeOn-time62%
DeltaCheapest$83Average$359FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$92Average$308FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$326FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$137Average$369FlexibilityNo cancel feeOn-time69%

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