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.

$92 CHEAP FLIGHTS from Pennsylvania to Chicago

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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, Feb 26 - Sat, Feb 27

12:46 pm - 2:19 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 33mnonstop

5:32 pm - 12:28 amORD Chicago O'Hare Intl-PHL Philadelphia

5h 56m1 stop Atlanta Hartsfield-Jackson

$181Frontier

Thu, Dec 10 - Sat, Dec 19

4:38 pm - 9:42 pmPHL Philadelphia-ORD Chicago O'Hare Intl

6h 04m1 stop Atlanta Hartsfield-Jackson

7:45 pm - 11:00 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 15mnonstop

$181Frontier

Sat, Jan 23 - Tue, Jan 26

7:30 am - 8:50 amPHL Philadelphia-MDW Chicago Midway

2h 20mnonstop

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

2h 00mnonstop

$257Southwest

Wed, Dec 2 - Mon, Dec 7

7:30 am - 8:50 amPHL Philadelphia-MDW Chicago Midway

2h 20mnonstop

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

1h 55mnonstop

$257Southwest

Wed, Dec 2 - Mon, Dec 7

9:22 am - 11:04 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 42mnonstop

8:30 am - 11:41 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 11mnonstop

$257American Airlines

Sat, Dec 12 - Mon, Dec 14

12:47 pm - 2:20 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 33mnonstop

5:47 pm - 9:00 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 13mnonstop

$257American Airlines

Wed, Jan 27 - Mon, Feb 1

9:45 am - 11:19 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 34mnonstop

9:00 am - 12:14 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$257United Airlines

Sat, Jan 23 - Mon, Jan 25

6:22 am - 7:56 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 34mnonstop

2:30 pm - 5:38 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 08mnonstop

$257United Airlines

Mon, Dec 28 - Wed, Dec 30

12:13 pm - 6:40 pmPHL Philadelphia-ORD Chicago O'Hare Intl

7h 27m1 stop Minneapolis St Paul

7:45 pm - 11:00 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 15mnonstop

$266Multiple Airlines

Tue, Dec 22 - Mon, Dec 28

4:56 pm - 6:40 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 44mnonstop

7:40 pm - 10:55 amORD Chicago O'Hare Intl-PHL Philadelphia

14h 15m1 stop Minneapolis St Paul

$279Multiple Airlines

Recent last minute flight deals from Pennsylvania to Chicago

Fri, Oct 2 - Fri, Oct 30

11:54 am - 1:30 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

4:42 pm - 7:58 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 16mnonstop

$226Frontier

Tue, Sep 29 - Fri, Oct 30

12:40 pm - 5:46 pmPHL Philadelphia-MDW Chicago Midway

6h 06m1 stop Atlanta Hartsfield-Jackson

6:42 pm - 7:21 amMDW Chicago Midway-PHL Philadelphia

11h 39m1 stop Atlanta Hartsfield-Jackson

$252Frontier

Tue, Sep 29 - Fri, Oct 30

6:25 pm - 7:35 pmPHL Philadelphia-MDW Chicago Midway

2h 10mnonstop

1:30 pm - 4:25 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$335Southwest

Tue, Sep 29 - Fri, Oct 30

7:15 am - 1:30 pmPHL Philadelphia-MDW Chicago Midway

7h 15m1 stop Nashville Intl

11:45 am - 2:40 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$345Southwest

Fri, Oct 2 - Mon, Nov 2

2:32 pm - 10:59 pmPIT Pittsburgh-ORD Chicago O'Hare Intl

9h 27m1 stop Orlando

1:00 pm - 7:54 pmORD Chicago O'Hare Intl-PIT Pittsburgh

5h 54m1 stop Boston Logan Intl

$360Multiple Airlines

Sat, Oct 3 - Sun, Oct 4

8:16 am - 9:10 amERI Erie-ORD Chicago O'Hare Intl

1h 54mnonstop

9:15 pm - 11:59 pmORD Chicago O'Hare Intl-ERI Erie

1h 44mnonstop

$379American Airlines

Sat, Oct 3 - Sat, Oct 10

10:37 am - 12:00 pmABE Allentown-Bethlehem-ORD Chicago O'Hare Intl

2h 23mnonstop

5:45 pm - 9:00 pmORD Chicago O'Hare Intl-ABE Allentown-Bethlehem

2h 15mnonstop

$380United Airlines

Sat, Oct 3 - Tue, Oct 6

2:32 pm - 10:59 pmPIT Pittsburgh-ORD Chicago O'Hare Intl

9h 27m1 stop Orlando

7:11 am - 7:26 pmORD Chicago O'Hare Intl-PIT Pittsburgh

11h 15m2 stops Fort Lauderdale Greenville

$385Multiple Airlines

Sat, Oct 3 - Sun, Oct 4

8:16 am - 9:10 amERI Erie-ORD Chicago O'Hare Intl

1h 54mnonstop

5:18 am - 11:16 amORD Chicago O'Hare Intl-ERI Erie

4h 58m1 stop Charlotte Douglas

$388American Airlines

Sat, Oct 3 - Sat, Oct 10

5:44 pm - 7:05 pmAVP Wilkes-Barre Scranton-ORD Chicago O'Hare Intl

2h 21mnonstop

5:59 pm - 9:08 pmORD Chicago O'Hare Intl-AVP Wilkes-Barre Scranton

2h 09mnonstop

$389United Airlines

Recent direct flight deals from Pennsylvania to Chicago

Mon, Dec 7 - Wed, Dec 23

6:50 pm - 8:29 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 39mnonstop

7:45 pm - 11:00 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 15mnonstop

$181Frontier

Wed, Dec 23 - Sun, Dec 27

4:56 pm - 6:40 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 44mnonstop

7:45 pm - 11:00 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 15mnonstop

$181Frontier

Wed, Dec 23 - Sun, Jan 3

4:56 pm - 6:40 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 44mnonstop

7:45 pm - 11:00 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 15mnonstop

$181Frontier

Sat, Jan 23 - Tue, Jan 26

7:30 am - 8:50 amPHL Philadelphia-MDW Chicago Midway

2h 20mnonstop

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

2h 00mnonstop

$257Southwest

Wed, Dec 2 - Mon, Dec 7

7:30 am - 8:50 amPHL Philadelphia-MDW Chicago Midway

2h 20mnonstop

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

1h 55mnonstop

$257Southwest

Wed, Dec 2 - Mon, Dec 7

9:22 am - 11:04 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 42mnonstop

8:30 am - 11:41 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 11mnonstop

$257American Airlines

Sat, Dec 12 - Mon, Dec 14

12:47 pm - 2:20 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 33mnonstop

5:47 pm - 9:00 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 13mnonstop

$257American Airlines

Wed, Jan 27 - Mon, Feb 1

9:45 am - 11:19 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 34mnonstop

9:00 am - 12:14 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$257United Airlines

Sat, Jan 23 - Mon, Jan 25

6:22 am - 7:56 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 34mnonstop

2:30 pm - 5:38 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 08mnonstop

$257United Airlines

Tue, Oct 20 - Tue, Oct 20

7:45 am - 8:50 amPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

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

2h 05mnonstop

$257Southwest

Useful Info

Low season	February
High season	July
Cheapest flight	$92

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

Most popular time to fly with an average 6% 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.

Verified travelerFlew 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

Schererville

Munster

Chesterton

Porter

Monticello

Saint John

Griffith

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$92 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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