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$94+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PHL
Jul 31 — Aug 71
Fri 7/31
Fri 8/7
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 July 1, 2026.

This Flysmarter 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:00 am
ORD
-
JFK
Nonstop2h 17m
JetBlue
Mon 8/108:00 pm
JFK
-
ORD
Nonstop2h 58m
JetBlue
Deal found 6/28$183
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:00 pm
ORD
-
LGA
Nonstop2h 25m
United Airlines
Thu 9/106:10 am
LGA
-
ORD
Nonstop2h 40m
United Airlines
Deal found 6/30$184
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:10 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Fri 9/116:00 am
LGA
-
MDW
Nonstop2h 15m
Southwest
Deal found 6/30$184
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.
Wed 9/91:00 pm
ORD
-
JFK
Nonstop2h 20m
JetBlue
Thu 9/1010:00 am
JFK
-
ORD
Nonstop2h 47m
JetBlue
Deal found 6/30$184
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:00 am
ORD
-
JFK
Nonstop2h 17m
JetBlue
Tue 7/217:05 am
JFK
-
ORD
Nonstop2h 45m
JetBlue
Deal found 6/28$186
This Delta deal was found by Cheapflights users on 7/1. 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.
Thu 8/66:00 am
ORD
-
LGA
Nonstop2h 09m
Delta
Tue 8/115:00 pm
LGA
-
ORD
Nonstop3h 12m
Delta
Deal found 7/1$187
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:50 am
MDW
-
LGA
Nonstop2h 10m
Southwest
Sat 8/85:50 pm
LGA
-
MDW
Nonstop2h 25m
Southwest
Deal found 6/30$187
This JetBlue deal was found by Cheapflights users on 7/1. 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.
Mon 8/176:00 am
ORD
-
JFK
Nonstop2h 17m
JetBlue
Tue 8/256:55 am
JFK
-
ORD
Nonstop2h 48m
JetBlue
Deal found 7/1$187
This American Airlines deal was found by Cheapflights users on 7/1. 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 8/86:00 am
ORD
-
LGA
Nonstop2h 13m
American Airlines
Mon 8/107:29 pm
LGA
-
ORD
Nonstop3h 01m
American Airlines
Deal found 7/1$188
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:43 am
ORD
-
EWR
Nonstop2h 19m
American Airlines
Wed 8/265:19 pm
EWR
-
ORD
Nonstop3h 01m
American Airlines
Deal found 6/29$188
This Delta deal was found by Cheapflights users on 7/1. 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.
Fri 8/78:12 pm
ORD
-
LGA
Nonstop2h 32m
Delta
Tue 8/118:30 pm
LGA
-
ORD
Nonstop2h 54m
Delta
Deal found 7/1$189
This Southwest deal was found by Cheapflights users on 6/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:40 pm
MDW
-
LGA
Nonstop2h 10m
Southwest
Sat 8/15:35 pm
LGA
-
MDW
Nonstop2h 50m
Southwest
Deal found 6/27$189

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 July 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$183
(Flysmarter)

One-way from

$94
(American Airlines)

Popular in

June

Cheapest in

October

Average price

$294

Good round-trip deal

$240 or less

Good one-way deal

$166 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. 14% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 1, 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
Quickest round-trip

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sun 9/13

5:25 am-8:25 am

Nonstop2h 00m

New York LaGuardia

Tue 9/15

6:00 am-7:15 am

Nonstop2h 15m

$184

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 9/12

2:29 pm-5:50 pm

Nonstop2h 21m

New York LaGuardia

Thu 9/17

6:00 am-7:29 am

Nonstop2h 29m

$187

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 8/22

7:05 am-10:19 am

Nonstop2h 14m

New York LaGuardia

Thu 8/27

6:00 am-7:29 am

Nonstop2h 29m

$187

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 8/8

7:50 am-11:00 am

Nonstop2h 10m

New York LaGuardia

Mon 8/10

6:00 am-7:15 am

Nonstop2h 15m

$187

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Mon 9/14

7:05 pm-10:33 pm

Nonstop2h 28m

New York LaGuardia

Sat 9/19

5:30 pm-7:15 pm

Nonstop2h 45m

$187

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Thu 7/30

1:00 pm-4:22 pm

Nonstop2h 22m

New York LaGuardia

Tue 8/4

7:25 pm-9:12 pm

Nonstop2h 47m

$189

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Fri 8/7

6:28 pm-9:58 pm

Nonstop2h 30m

Newark

Wed 8/12

9:45 pm-11:22 pm

Nonstop2h 37m

$189

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Tue 7/21

11:30 am-3:00 pm

Nonstop2h 30m

New York LaGuardia

Fri 7/24

8:45 pm-10:36 pm

Nonstop2h 51m

$189

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Tue 7/14

7:00 am-10:14 am

Nonstop2h 14m

New York LaGuardia

Tue 7/21

6:00 am-7:32 am

Nonstop2h 32m

$194

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 8/5

5:00 pm-8:22 pm

Nonstop2h 22m

New York LaGuardia

Sat 8/8

7:25 pm-9:12 pm

Nonstop2h 47m

$195

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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, October is the cheapest month in which you can book a flight from Chicago to Pennsylvania (average of $217). Flying from Chicago to Pennsylvania in February is currently the most expensive (average of $612). 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 July 1, 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 morning could potentially save you up to 13% on airfare.

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 July 1, 2026.

The most flights from CHI to USPA are scheduled on a Wednesday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

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

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

Booking 35 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Pennsylvania. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 June 27, 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. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 July 1, 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
7.9
Good
4,246 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
7.9
Good
4,246 reviews
Southwest
7.9
Good
4,246 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
9,910 reviews
Southwest
7.9
Good
4,246 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.1
Good
11,766 reviews
Southwest
7.9
Good
4,246 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.6
Fair
2,849 reviews
Southwest
7.9
Good
4,246 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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 $184, Southwest can have you in Pennsylvania from Chicago in 2h. There are 722 mi between Chicago and Pennsylvania. Most flights are nonstop.

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

    One-way options have recently been found by users for as low as $46 on Frontier. Other airlines that offer cheap prices include American Airlines from $48 and United Airlines from $78 one-way.

  • 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 - Newark and Chicago O'Hare Intl - New York LaGuardia.

  • 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: United Airlines (84%), Air New Zealand (79%), Japan Airlines( 78%).

  • What are the cheapest flights from Chicago to Pennsylvania?

    Looking for the cheapest flight from Chicago to Pennsylvania? While on average our users pay $757, our data indicates the cheapest price to be $97. The most popular route (Chicago O'Hare Intl - New York John F Kennedy Intl), is priced around $141.

  • 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, October is the cheapest month in which you can book a flight from Chicago to Pennsylvania (average of $217). Flying from Chicago to Pennsylvania in February is currently the most expensive (average of $612). 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 July 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$67Average$160FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$97Average$342FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$116Average$360FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$134Average$385FlexibilityNo cancel feeOn-time69%

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