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.

$91 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, Oct 11 - 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

$174Frontier

Wed, Oct 14 - Mon, Oct 19

12:35 pm - 6:31 pmPHL Philadelphia-ORD Chicago O'Hare Intl

6h 56m1 stop Atlanta Hartsfield-Jackson

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

10h 37m1 stop Atlanta Hartsfield-Jackson

$175Frontier

Tue, Nov 3 - Sat, Nov 7

4:05 pm - 9:30 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

6h 25m1 stop Newark

7:45 am - 10:53 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 08mnonstop

$181United Airlines

Wed, Nov 11 - Wed, Nov 18

1:16 pm - 2:50 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 34mnonstop

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

2h 15mnonstop

$185United Airlines

Sat, Nov 14 - Tue, Nov 17

6:37 pm - 8:30 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 53mnonstop

9:11 pm - 12:19 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 08mnonstop

$185American Airlines

Wed, Nov 11 - Wed, Nov 18

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

2h 39mnonstop

7:20 pm - 10:44 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 24mnonstop

$185American 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

$199Multiple Airlines

Wed, Nov 18 - Wed, Nov 18

6:30 am - 12:20 pmPHL Philadelphia-ORD Chicago O'Hare Intl

6h 50m1 stop Atlanta Hartsfield-Jackson

5:05 pm - 11:15 pmORD Chicago O'Hare Intl-PHL Philadelphia

5h 10m1 stop Detroit Metropolitan Wayne County

$205Delta

Sat, Oct 10 - Sat, Oct 17

2:00 pm - 8:38 pmPHL Philadelphia-ORD Chicago O'Hare Intl

7h 38m1 stop Atlanta Hartsfield-Jackson

11:09 am - 4:44 pmORD Chicago O'Hare Intl-PHL Philadelphia

4h 35m1 stop Detroit Metropolitan Wayne County

$205Delta

Thu, Oct 1 - Wed, Oct 7

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

$252Multiple Airlines

Recent last minute flight deals from Pennsylvania to Chicago

Thu, Sep 17 - Mon, Oct 19

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

$228Frontier

Sun, Sep 20 - Mon, Oct 19

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

$232Frontier

Thu, Sep 17 - Tue, Oct 6

6:55 am - 8:48 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 53mnonstop

10:34 am - 1:59 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 25mnonstop

$254American Airlines

Thu, Sep 17 - Tue, Oct 6

6:59 am - 8:51 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 52mnonstop

6:29 pm - 9:57 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 28mnonstop

$254American Airlines

Thu, Sep 17 - Tue, Oct 6

7:15 am - 12:59 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 44m1 stop Detroit Metropolitan Wayne County

6:00 pm - 9:40 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 40mnonstop

$264Delta

Wed, Sep 16 - Fri, Oct 16

9:10 am - 10:54 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

7:45 pm - 11:10 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$280United Airlines

Sat, Sep 19 - Sat, Nov 21

7:20 am - 9:00 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 40mnonstop

6:26 pm - 9:59 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 33mnonstop

$286United Airlines

Sat, Sep 19 - Wed, Sep 23

5:30 pm - 7:15 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 45mnonstop

2:29 pm - 5:50 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 21mnonstop

$293Delta

Wed, Sep 16 - Sat, Sep 19

1:00 pm - 7:01 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 01m1 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

$305JetBlue

Wed, Sep 16 - Sat, Sep 19

1:00 pm - 7:01 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 01m1 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

$305JetBlue

Recent direct flight deals from Pennsylvania to Chicago

Sun, Oct 11 - 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

$174Frontier

Thu, Oct 22 - Mon, Nov 2

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

2h 30mnonstop

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

2h 16mnonstop

$176Frontier

Sat, Nov 14 - Tue, Nov 17

6:37 pm - 8:30 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 53mnonstop

9:11 pm - 12:19 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 08mnonstop

$185American Airlines

Wed, Nov 11 - Wed, Nov 18

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

2h 39mnonstop

7:20 pm - 10:44 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 24mnonstop

$185American Airlines

Wed, Oct 28 - Sat, Oct 31

6:15 am - 7:51 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

8:50 am - 12:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$185United Airlines

Wed, Dec 30 - Wed, Jan 6

6:51 pm - 8:27 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

11:03 am - 2:15 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 12mnonstop

$185United Airlines

Sun, Nov 8 - Tue, Nov 10

6:59 am - 8:35 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 36mnonstop

7:00 am - 10:15 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$235Delta

Sun, Nov 15 - Tue, Dec 1

8:30 pm - 10:18 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 48mnonstop

7:00 am - 10:20 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 20mnonstop

$235Delta

Wed, Oct 14 - Fri, Oct 16

9:30 am - 11:24 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

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

2h 20mnonstop

$235JetBlue

Sat, Oct 3 - Wed, Oct 7

8:15 pm - 10:08 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 53mnonstop

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

2h 21mnonstop

$236JetBlue

Useful Info

Low season	February
High season	October
Cheapest flight	$91

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

Most popular time to fly and prices are also 8% lower on average.

Flight from Washington Dulles Airport 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

Chesterton

Munster

Porter

Monticello

Saint John

Griffith

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$91 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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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