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

Sun, Dec 13 - Mon, Jan 4

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

2h 39mnonstop

3:30 pm - 6:45 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 15mnonstop

$175Frontier

Fri, Dec 4 - Mon, Dec 7

7:34 am - 6:03 pmPHL Philadelphia-ORD Chicago O'Hare Intl

11h 29m1 stop Atlanta Hartsfield-Jackson

9:29 pm - 12:44 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 15mnonstop

$175Frontier

Wed, Dec 16 - Wed, Dec 16

3:59 pm - 5:39 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 40mnonstop

9:11 pm - 12:24 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 13mnonstop

$194American Airlines

Tue, Dec 8 - Tue, Dec 8

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

2h 45mnonstop

5:00 pm - 8:14 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$195American Airlines

Sat, Jan 23 - Tue, Jan 26

6:17 am - 7:53 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

6:25 pm - 9:40 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 15mnonstop

$199United Airlines

Sat, Jan 23 - Tue, Jan 26

4:55 pm - 6:31 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

6:25 pm - 9:40 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 15mnonstop

$199United Airlines

Tue, Dec 8 - Tue, Dec 8

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

2h 20mnonstop

6:25 pm - 9:25 pmMDW Chicago Midway-PHL Philadelphia

2h 00mnonstop

$199Southwest

Wed, Dec 9 - Sat, Dec 12

11:45 am - 1:00 pmPHL Philadelphia-MDW Chicago Midway

2h 15mnonstop

3:40 pm - 6:35 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$199Southwest

Mon, Dec 7 - Wed, Dec 9

7:25 pm - 2:30 pmPHL Philadelphia-ORD Chicago O'Hare Intl

20h 05m2 stops Tampa St. Petersburg Atlanta Hartsfield-Jackson

4:00 pm - 11:11 pmORD Chicago O'Hare Intl-PHL Philadelphia

6h 11m1 stop Atlanta Hartsfield-Jackson

$201Multiple Airlines

Fri, Dec 18 - Tue, Dec 29

12:19 pm - 6:40 pmPHL Philadelphia-ORD Chicago O'Hare Intl

7h 21m1 stop Minneapolis St Paul

4:18 pm - 7:37 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 19mnonstop

$240Multiple Airlines

Recent last minute flight deals from Pennsylvania to Chicago

Mon, Nov 9 - Thu, Nov 12

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

$182Frontier

Fri, Nov 6 - Mon, Nov 9

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

$229Frontier

Sat, Nov 7 - Thu, Nov 12

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

15h 19m1 stop Orlando

7:55 am - 8:14 pmORD Chicago O'Hare Intl-PIT Pittsburgh

35h 19m2 stops Fort Lauderdale Raleigh-Durham

$337Multiple Airlines

Mon, Nov 9 - Sat, Nov 21

10:40 am - 12:19 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 39mnonstop

7:20 pm - 10:27 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 07mnonstop

$380American Airlines

Mon, Nov 9 - Sat, Nov 21

6:30 am - 7:50 amMDT Harrisburg-ORD Chicago O'Hare Intl

2h 20mnonstop

3:55 pm - 6:57 pmORD Chicago O'Hare Intl-MDT Harrisburg

2h 02mnonstop

$394United Airlines

Mon, Nov 9 - Sat, Nov 21

7:05 pm - 11:30 pmMDT Harrisburg-ORD Chicago O'Hare Intl

5h 25m1 stop Philadelphia

8:49 pm - 11:49 pmORD Chicago O'Hare Intl-MDT Harrisburg

2h 00mnonstop

$404American Airlines

Mon, Nov 9 - Sat, Nov 21

5:05 pm - 8:17 pmMDT Harrisburg-ORD Chicago O'Hare Intl

4h 12m1 stop Detroit Metropolitan Wayne County

5:05 pm - 11:06 pmORD Chicago O'Hare Intl-MDT Harrisburg

5h 01m1 stop Detroit Metropolitan Wayne County

$414Delta

Fri, Nov 6 - Mon, Nov 9

1:18 pm - 1:42 pmPHL Philadelphia-ORD Chicago O'Hare Intl

25h 24m1 stop Fort Lauderdale

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

2h 22mnonstop

$414Multiple Airlines

Sat, Nov 7 - Tue, Nov 10

6:46 pm - 8:22 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

6:24 pm - 9:38 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$415United Airlines

Sat, Nov 7 - Sat, Nov 7

9:48 am - 12:59 pmPHL Philadelphia-ORD Chicago O'Hare Intl

4h 11m1 stop Detroit Metropolitan Wayne County

5:29 pm - 11:08 pmORD Chicago O'Hare Intl-PHL Philadelphia

4h 39m1 stop Detroit Metropolitan Wayne County

$435Delta

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

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

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