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$55+ Cheap flights from Chicago (CHI) to Pennsylvania

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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PHL
Apr 29 — May 61
Wed 4/29
Wed 5/6
1 adult, Economy
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Cheap flight deals from Chicago to Pennsylvania

Cheapest flights from Chicago to Pennsylvania
Explore the most affordable flight options available from Chicago to Pennsylvania. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 30, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/282:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Sat 5/22:38 pm
LGA
-
ORD
Nonstop2h 36m
Spirit Airlines
Deal found 3/30$96
This CheapOair deal was found by Cheapflights users on 3/27. 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.
Wed 4/152:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Tue 4/216:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Deal found 3/27$97
This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/212:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Fri 4/246:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Deal found 3/30$101
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/152:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Wed 4/226:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Deal found 3/29$103
This Expedia deal was found by Cheapflights users on 3/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Wed 5/66:29 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Deal found 3/29$104
This Booking.com deal was found by Cheapflights users on 3/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Wed 4/221:45 pm
EWR
-
MDW
1 stop18h 41m
Frontier
Deal found 3/27$104
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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.
Sat 4/2510:33 am
ORD
-
LGA
Nonstop2h 10m
Spirit Airlines
Tue 4/286:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Deal found 3/27$106
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 4/287:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Tue 5/55:55 am
EWR
-
MDW
1 stop6h 17m
Frontier
Deal found 3/27$106
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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.
Tue 4/147:31 pm
ORD
-
LGA
Nonstop2h 05m
Spirit Airlines
Sat 4/182:38 pm
LGA
-
ORD
Nonstop2h 36m
Spirit Airlines
Deal found 3/27$107
This Cheapflightsfares deal was found by Cheapflights users on 3/26. 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 4/86:01 pm
ORD
-
EWR
Nonstop2h 08m
Spirit Airlines
Wed 4/810:54 pm
EWR
-
ORD
Nonstop2h 28m
Spirit Airlines
Deal found 3/26$107
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 4/282:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Wed 5/66:29 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Deal found 3/27$108
This Trip.com deal was found by Cheapflights users on 3/27. 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.
Tue 4/212:15 pm
MDW
-
EWR
1 stop10h 01m
Frontier
Sat 4/2511:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Deal found 3/27$108

Find flight deals from Chicago to Pennsylvania

Keep the following information in mind while searching for Chicago to Pennsylvania flight deals. Data was last updated March 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$96
(Cheapflightsfares)

One-way from

$55
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$369

Good round-trip deal

$262 or less

Good one-way deal

$155 or less
Provider with most accurate pricing for Chicago (CHI)-Philadelphia flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Philadelphia flights.
Search Deals
From Chicago (CHI) to Pennsylvania
Search Deals
One-way flight from Chicago (CHI) to Pennsylvania
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Pennsylvania.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Pennsylvania.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Pennsylvania 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 March 30, 2026.
Use the filters below to find and compare flights from Chicago to Pennsylvania that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Tue 4/14

7:17 am-3:04 pm

1 stop6h 47m

Newark

Thu 4/16

10:08 am-11:42 am

Nonstop2h 34m

$132

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 5/30

5:45 pm-9:04 pm

Nonstop2h 19m

New York LaGuardia

Mon 6/1

8:45 pm-10:36 pm

Nonstop2h 51m

$161

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 5/1

7:50 pm-10:55 pm

Nonstop2h 05m

New York LaGuardia

Wed 5/6

8:55 pm-10:30 pm

Nonstop2h 35m

$168

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Fri 5/1

7:44 pm-10:59 pm

Nonstop2h 15m

New York LaGuardia

Wed 5/6

4:40 pm-6:39 pm

Nonstop2h 59m

$168

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 5/29

7:50 pm-10:55 pm

Nonstop2h 05m

New York LaGuardia

Mon 6/1

6:00 am-7:25 am

Nonstop2h 25m

$170

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Thu 5/7

7:00 am-10:18 am

Nonstop2h 18m

New York LaGuardia

Sat 5/9

2:50 pm-6:33 pm

1 stop4h 43m

$171

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 4/14

5:15 pm-8:20 pm

Nonstop2h 05m

New York LaGuardia

Thu 4/16

6:00 am-7:25 am

Nonstop2h 25m

$172

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Thu 4/23

8:31 am-11:50 am

Nonstop2h 19m

New York John F Kennedy Intl

Mon 4/27

6:00 am-7:41 am

Nonstop2h 41m

$177

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Fri 5/8

6:30 pm-9:53 pm

Nonstop2h 23m

New York LaGuardia

Mon 5/11

7:20 pm-9:05 pm

Nonstop2h 45m

$177

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Tue 5/19

7:05 am-10:21 am

Nonstop2h 16m

New York LaGuardia

Wed 5/20

6:00 am-7:47 am

Nonstop2h 47m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Best time to book a flight from Chicago to Pennsylvania

Have a flexible travel schedule? Discover the best time to fly to Pennsylvania from Chicago 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 Chicago to Pennsylvania

What is the cheapest month to book a flight from Chicago to Pennsylvania?

Currently, January is the cheapest month in which you can book a flight from Chicago to Pennsylvania (average of $59). Flying from Chicago to Pennsylvania in March is currently the most expensive (average of $167). 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 CHI to PA?

Find hourly flight availability from Chicago to Pennsylvania. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 30, 2026.

One of the essential ways to save on airfare from Chicago to Pennsylvania is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 11% on airfare.

What is the cheapest day to fly from Chicago to Pennsylvania?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Pennsylvania. Price data was last updated on March 28, 2026.

Travelers seeking maximum savings on their Chicago to Pennsylvania flight should consider departing on Thursday afternoons 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 Chicago to Pennsylvania

Explore weekly flight availability from Chicago to Pennsylvania. 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 March 30, 2026.

The most flights from CHI to USPA are scheduled on a Sunday (48 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (21 on average).

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

Reviews of airlines servicing Pennsylvania

Get insights into the airlines that provide service to Pennsylvania. 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 Pennsylvania. Reviews last updated March 30, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Pennsylvania have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,329 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,329 reviews
Southwest
8.0
Very good
4,329 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,514 reviews
Southwest
8.0
Very good
4,329 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,530 reviews
Southwest
8.0
Very good
4,329 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
3,010 reviews
Southwest
8.0
Very good
4,329 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Pennsylvania. 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 Chicago to Pennsylvania?

    For as low as $168, Spirit Airlines can have you in Pennsylvania from Chicago in 2h 05m. There are 722 mi between Chicago and Pennsylvania. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The most popular flight routes from Chicago to Pennsylvania are Chicago O'Hare Intl - New York John F Kennedy Intl, Chicago O'Hare Intl - New York LaGuardia and Chicago O'Hare Intl - Newark.

  • What are the most reliable airlines from Chicago to Pennsylvania?

    Before booking your flight to Pennsylvania from Chicago, check out the most reliable airlines to get you to your destination on time: Volaris (79%), Republic Airways (76%), Air Canada( 73%).

  • What are the cheapest flights from Chicago to Pennsylvania?

    Looking for the cheapest flight from Chicago to Pennsylvania? While on average our users pay $758, our data indicates the cheapest price to be $98. The most popular route (Chicago O'Hare Intl - New York John F Kennedy Intl), is priced around $159.

  • Can I find deals for flights from Chicago to Pennsylvania that include hotel bookings?

    Yes. In addition to deals on Chicago to Pennsylvania flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Pennsylvania?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Pennsylvania.

  • Can I find deals for business class flights from Chicago to Pennsylvania?

    Yes. Cheapflights offers flight deals from Chicago to Pennsylvania 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 Chicago to Pennsylvania?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Pennsylvania (average of $59). Flying from Chicago to Pennsylvania in March is currently the most expensive (average of $167). 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

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Alternative routes for Chicago to Pennsylvania

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Chicago to Pennsylvania

Discover the top 4 airlines that operate flights from Chicago to Pennsylvania. 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 March 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$67Average$166FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$101Average$342FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$103Average$365FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$116Average$375FlexibilityNo cancel feeOn-time63%

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