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.

$89 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

Thu, Feb 25 - Sat, Feb 27

6:37 pm - 11:46 pmPHL Philadelphia-MDW Chicago Midway

6h 09m1 stop Atlanta Hartsfield-Jackson

1:18 pm - 12:28 amMDW Chicago Midway-PHL Philadelphia

10h 10m1 stop Atlanta Hartsfield-Jackson

$179Frontier

Thu, Jan 7 - Sun, Jan 10

10:51 am - 4:26 pmPHL Philadelphia-MDW Chicago Midway

6h 35m1 stop Atlanta Hartsfield-Jackson

5:21 pm - 12:31 amMDW Chicago Midway-PHL Philadelphia

6h 10m1 stop Atlanta Hartsfield-Jackson

$180Frontier

Thu, Dec 3 - Mon, Dec 7

6:00 am - 3:30 pmPHL Philadelphia-MDW Chicago Midway

10h 30m1 stop Lambert-St Louis

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

1h 55mnonstop

$181Southwest

Sun, Dec 6 - Sun, Dec 13

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

2h 10mnonstop

3:50 pm - 6:45 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$181Southwest

Tue, Dec 1 - Fri, Dec 4

3:46 pm - 5:29 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 43mnonstop

7:20 pm - 10:34 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$181American Airlines

Tue, Dec 1 - Fri, Dec 4

6:19 am - 7:55 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

8:59 am - 12:13 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$181United Airlines

Tue, Dec 1 - Thu, Dec 3

6:19 am - 7:55 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

6:54 am - 9:57 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 03mnonstop

$181United Airlines

Fri, Jan 15 - Mon, Jan 18

6:00 am - 8:58 amPHL Philadelphia-ORD Chicago O'Hare Intl

3h 58m1 stop Detroit Metropolitan Wayne County

5:55 pm - 12:51 amORD Chicago O'Hare Intl-PHL Philadelphia

5h 56m1 stop Atlanta Hartsfield-Jackson

$183Delta

Fri, Jan 15 - Mon, Jan 18

6:00 am - 8:45 amPHL Philadelphia-MDW Chicago Midway

3h 45m1 stop Detroit Metropolitan Wayne County

5:25 pm - 12:51 amMDW Chicago Midway-PHL Philadelphia

6h 26m1 stop Atlanta Hartsfield-Jackson

$185Delta

Wed, Dec 2 - Sat, Dec 5

6:34 pm - 8:23 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 49mnonstop

12:59 pm - 4:09 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 10mnonstop

$199American Airlines

Recent last minute flight deals from Pennsylvania to Chicago

Wed, Oct 28 - Thu, Oct 29

8:30 am - 6:16 pmPHL Philadelphia-ORD Chicago O'Hare Intl

10h 46m1 stop Atlanta Hartsfield-Jackson

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

2h 16mnonstop

$234Frontier

Fri, Oct 30 - Mon, Nov 9

7:50 am - 3:37 pmPHL Philadelphia-ORD Chicago O'Hare Intl

8h 47m1 stop Fort Lauderdale

7:50 pm - 7:21 amORD Chicago O'Hare Intl-PHL Philadelphia

10h 31m1 stop Atlanta Hartsfield-Jackson

$243Frontier

Tue, Oct 27 - Wed, Dec 2

11:25 am - 12:30 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

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

1h 55mnonstop

$307Southwest

Tue, Oct 27 - Wed, Dec 2

5:30 am - 2:05 pmPHL Philadelphia-MDW Chicago Midway

9h 35m1 stop Denver Intl

11:25 am - 2:15 pmMDW Chicago Midway-PHL Philadelphia

1h 50mnonstop

$317Southwest

Thu, Oct 29 - Sat, Oct 31

6:27 pm - 8:46 amPIT Pittsburgh-ORD Chicago O'Hare Intl

15h 19m1 stop Orlando

8:00 am - 5:27 pmORD Chicago O'Hare Intl-PIT Pittsburgh

8h 27m1 stop Fort Lauderdale

$320Multiple Airlines

Fri, Oct 30 - Sun, Nov 1

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

2h 03mnonstop

9:15 pm - 11:53 pmORD Chicago O'Hare Intl-ERI Erie

1h 38mnonstop

$399American Airlines

Wed, Oct 28 - Wed, Nov 4

6:47 pm - 8:26 pmABE Allentown-Bethlehem-ORD Chicago O'Hare Intl

2h 39mnonstop

7:49 pm - 10:59 pmORD Chicago O'Hare Intl-ABE Allentown-Bethlehem

2h 10mnonstop

$400American Airlines

Fri, Oct 30 - Sun, Nov 1

7:50 am - 3:37 pmPHL Philadelphia-ORD Chicago O'Hare Intl

8h 47m1 stop Fort Lauderdale

7:00 am - 11:43 pmORD Chicago O'Hare Intl-PHL Philadelphia

15h 43m1 stop Fort Lauderdale

$406Multiple Airlines

Sun, Nov 1 - Sat, Nov 14

6:03 pm - 11:57 pmABE Allentown-Bethlehem-ORD Chicago O'Hare Intl

6h 54m1 stop Atlanta Hartsfield-Jackson

3:00 pm - 10:27 pmORD Chicago O'Hare Intl-ABE Allentown-Bethlehem

6h 27m1 stop Atlanta Hartsfield-Jackson

$414Delta

Sun, Nov 1 - Sat, Nov 14

6:39 am - 4:32 pmABE Allentown-Bethlehem-ORD Chicago O'Hare Intl

10h 53m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County

5:30 am - 12:04 pmORD Chicago O'Hare Intl-ABE Allentown-Bethlehem

5h 34m1 stop Atlanta Hartsfield-Jackson

$419Delta

Recent direct flight deals from Pennsylvania to Chicago

Tue, Dec 1 - Fri, Dec 4

3:46 pm - 5:29 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 43mnonstop

7:20 pm - 10:34 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$181American Airlines

Fri, Nov 6 - Fri, Nov 13

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

$181Frontier

Tue, Dec 1 - Thu, Dec 3

6:19 am - 7:55 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

6:54 am - 9:57 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 03mnonstop

$181United Airlines

Tue, Dec 1 - Fri, Dec 4

6:19 am - 7:55 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

8:59 am - 12:13 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$181United Airlines

Sun, Dec 6 - Sun, Dec 13

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

2h 10mnonstop

3:50 pm - 6:45 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$181Southwest

Fri, Nov 20 - Mon, Nov 23

6:31 pm - 8:15 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 44mnonstop

9:20 pm - 12:30 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 10mnonstop

$183Frontier

Mon, Dec 28 - Wed, Dec 30

12:39 pm - 2:12 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 33mnonstop

3:34 pm - 6:49 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 15mnonstop

$184Frontier

Thu, Jan 14 - Fri, Jan 15

5:20 pm - 6:40 pmPHL Philadelphia-MDW Chicago Midway

2h 20mnonstop

2:50 pm - 5:40 pmMDW Chicago Midway-PHL Philadelphia

1h 50mnonstop

$197Southwest

Wed, Dec 2 - Sat, Dec 5

6:34 pm - 8:23 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 49mnonstop

12:59 pm - 4:09 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 10mnonstop

$199American Airlines

Wed, Dec 9 - Sat, Dec 12

12:35 pm - 2:20 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 45mnonstop

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

2h 13mnonstop

$199American Airlines

Useful Info

Low season	February
High season	July
Cheapest flight	$89

Best time to beat the crowds with an average 9% drop in price.

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

Flight from Philadelphia to Chicago O'Hare Airport

Verified travelerFlew with United Airlines-Oct 2026

Check your watch carefully! I was afraid I was going to be late for my flight because I thought my watch said it was an hour later than it actually was. Also, if you need special services, like a wheelchair ride between flights, be sure you make it at the same time you make your reservation and get a confirmation for it.

NicholFlew with United Airlines-Oct 2026

Ensure you leave yourself enough time at the airport. It is a busy airport so can take a little bit to get through security if you don't have TSA precheck.

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

Munster

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

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$89 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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High season

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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

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