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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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
jul. 5 — jul. 121
sáb. 7/5
sáb. 7/12
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 junio 30, 2025.

Round-trip from

$127
(Priceline)

One-way from

$64
(Priceline)

Popular in

March

Cheapest in

September

Average price

$217

Good round-trip deal

$190 or less

Good one-way deal

$104 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. 24% potential increase in price ($73 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in June 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 junio 30, 2025.

This Priceline deal was found by Cheapflights users on 6/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/185:55 amEWR - ORD
1 stop6h 30mMultiple Airlines
dom. 10/195:10 pmORD - EWR
Nonstop2h 18mMultiple Airlines
Deal found 6/28$125
This Cheapflightsfares deal was found by Cheapflights users on 6/29. 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.
jue. 10/239:33 pmEWR - ORD
Nonstop2h 37mSpirit Airlines
dom. 10/265:10 pmORD - EWR
Nonstop2h 18mSpirit Airlines
Deal found 6/29$129
This JetBlue deal was found by Cheapflights users on 6/30. 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.
sáb. 8/308:30 pmJFK - ORD
Nonstop2h 58mJetBlue
mié. 9/36:10 amORD - JFK
Nonstop2h 19mJetBlue
Deal found 6/30$137
This Priceline deal was found by Cheapflights users on 6/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/199:00 amJFK - MDW
1 stop7h 58mFrontier
lun. 9/225:04 pmMDW - JFK
1 stop6h 38mFrontier
Deal found 6/28$137
This Delta deal was found by Cheapflights users on 6/30. 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.
mar. 9/28:30 pmLGA - ORD
Nonstop2h 50mDelta
mié. 9/37:10 amORD - LGA
Nonstop2h 15mDelta
Deal found 6/30$137
This Priceline deal was found by Cheapflights users on 6/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/196:30 amLGA - MDW
1 stop10h 28mFrontier
lun. 9/225:04 pmMDW - LGA
1 stop5h 27mFrontier
Deal found 6/28$137
This FlightHub deal was found by Cheapflights users on 6/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/293:13 pmLGA - ORD
Nonstop2h 38mSpirit Airlines
mié. 10/111:13 amORD - LGA
Nonstop2h 05mSpirit Airlines
Deal found 6/28$138
This Priceline deal was found by Cheapflights users on 6/29. 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.
mar. 7/226:30 amLGA - ORD
1 stop11h 08mMultiple Airlines
mié. 7/238:09 amORD - LGA
1 stop8h 21mMultiple Airlines
Deal found 6/29$139
This Priceline deal was found by Cheapflights users on 6/30. 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.
mié. 8/66:30 amLGA - ORD
1 stop10h 34mFrontier
sáb. 8/99:55 amORD - LGA
1 stop10h 04mFrontier
Deal found 6/30$140
This Priceline deal was found by Cheapflights users on 6/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/2912:30 pmJFK - ORD
1 stop12h 31mFrontier
sáb. 9/65:45 pmORD - JFK
1 stop5h 58mFrontier
Deal found 6/28$141
This Priceline deal was found by Cheapflights users on 6/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/511:15 amEWR - MDW
1 stop5h 43mFrontier
mar. 9/92:32 pmMDW - EWR
1 stop9h 02mFrontier
Deal found 6/28$141
This Trip.com deal was found by Cheapflights users on 6/29. 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.
mié. 8/611:04 amEWR - ORD
1 stop6h 00mFrontier
mar. 8/125:38 pmORD - EWR
1 stop6h 00mFrontier
Deal found 6/29$148

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 junio 30, 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

NewarkChicago

EWR - ORD

EWRORD

Newark

sáb. 10/18

5:55 am-11:25 am

1 stop6h 30m

Chicago O'Hare Intl

dom. 10/19

5:10 pm-8:28 pm

Nonstop2h 18m

$125

NewarkChicago

EWR - ORD

EWRORD

Newark

jue. 10/23

9:33 pm-11:10 pm

Nonstop2h 37m

Chicago O'Hare Intl

dom. 10/26

5:10 pm-8:28 pm

Nonstop2h 18m

$129

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

sáb. 8/30

8:30 pm-10:28 pm

Nonstop2h 58m

Chicago O'Hare Intl

mié. 9/3

6:10 am-9:29 am

Nonstop2h 19m

$137

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

vie. 9/19

9:00 am-3:58 pm

1 stop7h 58m

Chicago Midway

lun. 9/22

5:04 pm-12:42 am

1 stop6h 38m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mar. 9/2

8:30 pm-10:20 pm

Nonstop2h 50m

Chicago O'Hare Intl

mié. 9/3

7:10 am-10:25 am

Nonstop2h 15m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

vie. 9/19

6:30 am-3:58 pm

1 stop10h 28m

Chicago Midway

lun. 9/22

5:04 pm-11:31 pm

1 stop5h 27m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mié. 8/13

6:30 am-4:04 pm

1 stop10h 34m

Chicago O'Hare Intl

sáb. 8/16

9:55 am-8:59 pm

1 stop10h 04m

$138

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mar. 7/22

6:30 am-4:38 pm

1 stop11h 08m

Chicago O'Hare Intl

mié. 7/23

8:09 am-5:30 pm

1 stop8h 21m

$139

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

sáb. 7/26

4:58 pm-11:27 pm

1 stop7h 29m

Chicago O'Hare Intl

mar. 7/29

5:51 am-9:00 am

Nonstop2h 09m

$141

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

vie. 8/29

12:30 pm-12:01 am

1 stop12h 31m

Chicago O'Hare Intl

sáb. 9/6

5:45 pm-12:43 am

1 stop5h 58m

$141

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

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 junio 30, 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 junio 30, 2025.

The most flights from USPA to CHI are scheduled on a Monday (55 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (34 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated junio 30, 2025.
Read through reviews of airlines operating flights from Pennsylvania to Chicago, such as Southwest, Delta, and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,969 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,852 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,920 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

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

    $64 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and JetBlue, with prices starting from $67 and $79, 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 Air Canada (86%), ANA (86%) or SWISS (84%) 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 $1,211 for a flight from Pennsylvania to Chicago. The cheapest flight overall is $87 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $137.

  • 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 Pennsylvania?

Book flights to Pennsylvania if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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.
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
San Francisco to O'Hare Intl flights
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Philadelphia to O'Hare Intl flights
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Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Denver to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Atlanta to Midway flights
Atlanta to O'Hare Intl flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
Hobby to O'Hare Intl flights
Ontario to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Orlando to O'Hare Intl flights
Austin to O'Hare Intl flights
Dulles Intl to Midway flights
Tampa to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Portland to O'Hare Intl flights
LaGuardia to Midway flights
Fort Lauderdale to O'Hare Intl flights
San Francisco to Midway flights
Minneapolis to O'Hare Intl flights
San Diego to O'Hare Intl flights
Love Field to O'Hare Intl flights
Hobby to Midway flights
Burbank to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Miami to O'Hare Intl flights
Baltimore to Midway flights
Denver to Midway flights
Philadelphia to Midway flights
Minneapolis to Midway flights
Newark to St. Louis flights
Oakland to O'Hare Intl flights
Orlando to Midway flights
Sky Harbor Intl to Midway flights
San Jose to O'Hare Intl flights
Boston to Midway flights
Love Field 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 junio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$50Average$138FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$352FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$119Average$349FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$126Average$310FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$138Average$366FlexibilityNo cancel feeOn-time69%

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