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

Sat, Oct 24 - Mon, Oct 26

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

2h 30mnonstop

7:44 pm - 7:21 amORD Chicago O'Hare Intl-PHL Philadelphia

10h 37m1 stop Atlanta Hartsfield-Jackson

$168Frontier

Tue, Oct 20 - Thu, Oct 22

5:22 pm - 6:31 pmPHL Philadelphia-ORD Chicago O'Hare Intl

26h 09m1 stop Atlanta Hartsfield-Jackson

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

2h 23mnonstop

$168Frontier

Fri, Sep 25 - Fri, Oct 2

6:00 am - 10:53 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

5h 53m1 stop Newark

9:00 am - 12:08 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 08mnonstop

$208United Airlines

Mon, Oct 5 - Sat, Oct 10

5:59 pm - 11:51 amPHL Philadelphia-ORD Chicago O'Hare Intl

18h 52m2 stops Tampa St. Petersburg Atlanta Hartsfield-Jackson

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

2h 23mnonstop

$221Multiple Airlines

Sun, Nov 1 - Tue, Nov 3

10:47 pm - 12:01 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 14mnonstop

5:00 am - 11:44 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

5h 44m1 stop Newark

$231United Airlines

Sat, Oct 17 - Tue, Oct 20

1:00 pm - 7:14 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 14m1 stop Boston Logan Intl

9:38 am - 5:29 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

6h 51m1 stop Boston Logan Intl

$235JetBlue

Mon, Nov 23 - Thu, Nov 26

6:35 pm - 8:30 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 55mnonstop

6:29 am - 9:37 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 08mnonstop

$237American 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

$237American Airlines

Tue, Sep 22 - Wed, Sep 30

1:00 pm - 6:23 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 23m1 stop Atlanta Hartsfield-Jackson

10:59 am - 2:20 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 21mnonstop

$244Multiple Airlines

Sat, Oct 17 - Tue, Oct 20

1:00 pm - 7:14 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 14m1 stop Boston Logan Intl

6:10 am - 9:30 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

$251JetBlue

Recent last minute flight deals from Pennsylvania to Chicago

Sat, Sep 12 - Fri, Sep 25

10:29 pm - 9:20 amEWR Newark-ORD Chicago O'Hare Intl

11h 51m1 stop Atlanta Hartsfield-Jackson

3:50 pm - 1:01 amORD Chicago O'Hare Intl-EWR Newark

8h 11m1 stop Orlando

$240Frontier

Tue, Sep 15 - Mon, Sep 28

1:30 pm - 8:29 pmEWR Newark-ORD Chicago O'Hare Intl

7h 59m1 stop Dallas/Fort Worth

3:50 pm - 1:01 amORD Chicago O'Hare Intl-EWR Newark

8h 11m1 stop Orlando

$244Frontier

Thu, Sep 10 - Mon, Sep 28

8:10 am - 9:58 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

7:00 am - 10:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 27mnonstop

$277JetBlue

Tue, Sep 15 - Sat, Sep 26

1:00 pm - 6:23 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 23m1 stop Atlanta Hartsfield-Jackson

7:00 am - 10:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 27mnonstop

$284Multiple Airlines

Tue, Sep 15 - Sat, Sep 26

8:10 am - 9:58 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

7:00 am - 10:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 27mnonstop

$285JetBlue

Sat, Sep 12 - Sun, Sep 27

10:04 pm - 11:50 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 46mnonstop

6:00 am - 9:14 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 14mnonstop

$286American Airlines

Thu, Sep 10 - Mon, Sep 28

1:00 pm - 6:23 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 23m1 stop Atlanta Hartsfield-Jackson

7:00 am - 10:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 27mnonstop

$293Multiple Airlines

Sat, Sep 12 - Sun, Sep 27

7:30 am - 11:41 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

5h 11m1 stop Washington, D.C. Reagan-National

6:59 am - 10:10 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 11mnonstop

$296American Airlines

Tue, Sep 15 - Tue, Sep 22

9:35 pm - 10:55 pmLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

7:20 am - 10:20 amMDW Chicago Midway-LGA New York LaGuardia

2h 00mnonstop

$301Southwest

Tue, Sep 15 - Sat, Sep 19

9:35 pm - 10:55 pmLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

3:10 pm - 6:15 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$301Southwest

Recent direct flight deals from Pennsylvania to Chicago

Sun, Oct 4 - Sat, Oct 10

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

2h 36mnonstop

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

2h 23mnonstop

$168Frontier

Fri, Oct 2 - Sat, Oct 10

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

2h 36mnonstop

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

2h 23mnonstop

$168Frontier

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

$237American Airlines

Mon, Nov 23 - Thu, Nov 26

6:35 pm - 8:30 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 55mnonstop

6:29 am - 9:37 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 08mnonstop

$237American Airlines

Tue, Oct 27 - Sat, Oct 31

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

2h 36mnonstop

7:45 pm - 10:57 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 12mnonstop

$237United Airlines

Tue, Sep 29 - Thu, Oct 1

6:55 pm - 8:25 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 30mnonstop

11:25 am - 2:43 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 18mnonstop

$237United Airlines

Fri, Oct 2 - Sun, Oct 18

8:07 pm - 9:59 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

6:10 am - 9:30 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

$258JetBlue

Fri, Oct 2 - Sun, Oct 4

8:07 pm - 9:59 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

7:00 am - 10:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 27mnonstop

$258JetBlue

Sat, Oct 3 - Mon, Oct 5

9:25 am - 10:55 amLGA New York LaGuardia-MDW Chicago Midway

2h 30mnonstop

5:10 am - 8:15 amMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$267Southwest

Fri, Oct 16 - Mon, Oct 19

9:00 pm - 10:25 pmLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

7:35 pm - 10:45 pmMDW Chicago Midway-LGA New York LaGuardia

2h 10mnonstop

$267Southwest

Useful Info

Low season	February
High season	October
Cheapest flight	$92

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

Most popular time to fly and prices are also 10% lower on average.

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

Munster

Schererville

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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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

Cabin class types available on flights to Pennsylvania

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Find deals for your return flight