How does KAYAK find such low prices on flights from Pennsylvania to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Pennsylvania to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Pennsylvania to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Pennsylvania is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Pennsylvania to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Pennsylvania with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Pennsylvania to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Pennsylvania up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$90 CHEAP FLIGHTS from Pennsylvania to Chicago

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Flight Deals

Cheap Flights from Pennsylvania to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Pennsylvania to Chicago

Fri, Nov 13 - Sun, Nov 15

9:09 pm - 10:43 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 34mnonstop

4:42 pm - 8:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 22mnonstop

$184Frontier

Thu, Nov 12 - Sun, Nov 15

9:09 pm - 10:43 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 34mnonstop

4:42 pm - 8:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 22mnonstop

$184Frontier

Thu, Oct 29 - Sat, Oct 31

3:20 pm - 4:25 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

12:55 pm - 4:00 pmMDW Chicago Midway-PHL Philadelphia

2h 05mnonstop

$185Southwest

Mon, Nov 2 - Wed, Nov 4

11:40 am - 12:50 pmPHL Philadelphia-MDW Chicago Midway

2h 10mnonstop

8:10 am - 11:05 amMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$185Southwest

Thu, Jan 21 - Tue, Jan 26

10:46 am - 12:23 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 37mnonstop

7:29 pm - 10:37 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 08mnonstop

$185American Airlines

Thu, Nov 12 - Sat, Nov 14

5:52 am - 7:27 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 35mnonstop

6:29 am - 9:39 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 10mnonstop

$185American Airlines

Mon, Nov 9 - Thu, Nov 12

10:54 am - 12:29 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 35mnonstop

8:50 am - 12:05 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 15mnonstop

$185United Airlines

Thu, Dec 24 - Tue, Dec 29

1:01 pm - 2:37 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

7:25 am - 10:30 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 05mnonstop

$185United Airlines

Thu, Nov 5 - Sat, Nov 7

6:10 am - 9:32 amPHL Philadelphia-MDW Chicago Midway

4h 22m1 stop Detroit Metropolitan Wayne County

9:29 am - 4:44 pmMDW Chicago Midway-PHL Philadelphia

6h 15m1 stop Detroit Metropolitan Wayne County

$205Delta

Wed, Nov 4 - Sat, Nov 7

9:48 am - 12:47 pmPHL Philadelphia-MDW Chicago Midway

3h 59m1 stop Detroit Metropolitan Wayne County

6:44 pm - 11:08 pmMDW Chicago Midway-PHL Philadelphia

3h 24m1 stop Detroit Metropolitan Wayne County

$205Delta

Recent last minute flight deals from Pennsylvania to Chicago

Sat, Oct 10 - Sat, Oct 17

9:09 pm - 10:39 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 30mnonstop

4:41 pm - 8:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 23mnonstop

$209Frontier

Tue, Oct 13 - Wed, Oct 14

8:30 am - 6:31 pmPHL Philadelphia-ORD Chicago O'Hare Intl

11h 01m1 stop Atlanta Hartsfield-Jackson

6:00 am - 6:15 pmORD Chicago O'Hare Intl-PHL Philadelphia

11h 15m1 stop Atlanta Hartsfield-Jackson

$210Frontier

Tue, Oct 13 - Tue, Oct 20

6:00 am - 7:33 amABE Allentown-Bethlehem-ORD Chicago O'Hare Intl

2h 33mnonstop

2:33 pm - 5:47 pmORD Chicago O'Hare Intl-ABE Allentown-Bethlehem

2h 14mnonstop

$380American Airlines

Fri, Oct 9 - Fri, Nov 20

7:51 pm - 7:51 amPIT Pittsburgh-ORD Chicago O'Hare Intl

13h 00m1 stop Orlando

11:00 am - 6:26 pmORD Chicago O'Hare Intl-PIT Pittsburgh

6h 26m1 stop Boston Logan Intl

$384Multiple Airlines

Fri, Oct 9 - Sun, Oct 11

8:07 am - 9:10 amERI Erie-ORD Chicago O'Hare Intl

2h 03mnonstop

5:00 am - 11:21 amORD Chicago O'Hare Intl-ERI Erie

5h 21m1 stop Charlotte Douglas

$388American Airlines

Sun, Oct 11 - Sun, Oct 18

10:37 am - 11:58 amABE Allentown-Bethlehem-ORD Chicago O'Hare Intl

2h 21mnonstop

6:25 am - 9:35 amORD Chicago O'Hare Intl-ABE Allentown-Bethlehem

2h 10mnonstop

$394United Airlines

Tue, Oct 13 - Tue, Oct 20

6:30 am - 7:41 amMDT Harrisburg-ORD Chicago O'Hare Intl

2h 11mnonstop

1:55 pm - 4:52 pmORD Chicago O'Hare Intl-MDT Harrisburg

1h 57mnonstop

$394United Airlines

Sat, Oct 10 - Tue, Oct 13

10:15 am - 11:25 amPHL Philadelphia-MDW Chicago Midway

2h 10mnonstop

6:00 pm - 9:05 pmMDW Chicago Midway-PHL Philadelphia

2h 05mnonstop

$395Southwest

Tue, Oct 13 - Wed, Oct 14

1:20 pm - 2:25 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

7:45 am - 10:40 amMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$395Southwest

Sat, Oct 10 - Mon, Oct 12

5:20 pm - 11:43 pmPHL Philadelphia-MDW Chicago Midway

7h 23m1 stop Atlanta Hartsfield-Jackson

1:26 pm - 6:41 pmMDW Chicago Midway-PHL Philadelphia

4h 15m1 stop Knoxville McGhee Tyson

$402Multiple Airlines

Recent direct flight deals from Pennsylvania to Chicago

Fri, Nov 13 - Sun, Nov 15

9:09 pm - 10:43 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 34mnonstop

4:42 pm - 8:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 22mnonstop

$184Frontier

Thu, Nov 12 - Sun, Nov 15

9:09 pm - 10:43 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 34mnonstop

4:42 pm - 8:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 22mnonstop

$184Frontier

Thu, Oct 29 - Sat, Oct 31

3:20 pm - 4:25 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

12:55 pm - 4:00 pmMDW Chicago Midway-PHL Philadelphia

2h 05mnonstop

$185Southwest

Mon, Nov 2 - Wed, Nov 4

11:40 am - 12:50 pmPHL Philadelphia-MDW Chicago Midway

2h 10mnonstop

8:10 am - 11:05 amMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$185Southwest

Thu, Jan 21 - Tue, Jan 26

10:46 am - 12:23 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 37mnonstop

7:29 pm - 10:37 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 08mnonstop

$185American Airlines

Thu, Nov 12 - Sat, Nov 14

5:52 am - 7:27 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 35mnonstop

6:29 am - 9:39 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 10mnonstop

$185American Airlines

Mon, Nov 9 - Thu, Nov 12

10:54 am - 12:29 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 35mnonstop

8:50 am - 12:05 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 15mnonstop

$185United Airlines

Thu, Dec 24 - Tue, Dec 29

1:01 pm - 2:37 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

7:25 am - 10:30 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 05mnonstop

$185United Airlines

Fri, Oct 23 - Mon, Oct 26

9:09 pm - 10:39 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 30mnonstop

4:41 pm - 8:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 23mnonstop

$185Frontier

Thu, Nov 5 - Mon, Nov 9

4:03 pm - 4:54 pmPIT Pittsburgh-ORD Chicago O'Hare Intl

1h 51mnonstop

5:00 pm - 7:43 pmORD Chicago O'Hare Intl-PIT Pittsburgh

1h 43mnonstop

$393Alaska Airlines

Useful Info

Low season	February
High season	July
Cheapest flight	$90

Best time to beat the crowds with an average 11% drop in price.

Most popular time to fly with an average 5% increase in price.

Flight from Philadelphia to Chicago O'Hare Airport

NFlew with United Airlines-Jul 2026

You need to check your own bags in, meaning you wait I line to print the ticket, put the tab on yourself and then go to another line to make sure the suitcase gets placed on the plane and under the 50lb weight limit. A lot of back and forth.

AdamFlew with American Airlines-Jul 2024

Fly out the night before you have anything to do in Chicago so you don’t get delayed and miss out on plans

How does KAYAK find such low prices on flights from Pennsylvania to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Pennsylvania to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Pennsylvania to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Pennsylvania is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Pennsylvania to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Pennsylvania with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Pennsylvania to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Pennsylvania up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Chesterton

Schererville

Munster

Porter

Monticello

Saint John

Griffith

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$90 Find Cheap Flights from Pennsylvania to Chicago - Compare and Save

Cheap Flights from Pennsylvania to Chicago

Recent round-trip flight deals from Pennsylvania to Chicago

Recent one-way flight deals from Pennsylvania to Chicago

Recent last minute flight deals from Pennsylvania to Chicago

Recent direct flight deals from Pennsylvania to Chicago

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Flights from Pennsylvania to Chicago: the best tips from KAYAK users

FAQs for booking flights from Pennsylvania to Chicago

Traveling to a place near Chicago?

More options for your flight to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Cabin class types available on flights to Pennsylvania

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Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight