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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Flight Deals

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, Nov 5 - Sun, Nov 8

9:09 pm - 10:43 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 34mnonstop

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

2h 16mnonstop

$167Frontier

Sun, Sep 6 - Sun, Sep 6

10:22 am - 11:55 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 33mnonstop

8:30 pm - 11:53 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 23mnonstop

$168Frontier

Thu, Sep 24 - Mon, Sep 28

6:30 am - 7:58 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 28mnonstop

6:55 pm - 10:00 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$178American Airlines

Thu, Sep 17 - Mon, Sep 21

3:58 pm - 5:28 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 30mnonstop

8:55 pm - 11:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$178American Airlines

Tue, Dec 29 - Thu, Jan 7

7:30 pm - 11:50 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

5h 20m1 stop Atlanta Hartsfield-Jackson

7:00 am - 11:53 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

3h 53m1 stop Detroit Metropolitan Wayne County

$197Delta

Mon, Oct 5 - Wed, Oct 7

7:40 pm - 11:59 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

5h 19m1 stop Atlanta Hartsfield-Jackson

10:30 am - 4:37 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

5h 07m1 stop New York John F Kennedy Intl

$197Delta

Mon, Sep 28 - Mon, Sep 28

8:20 am - 9:38 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 18mnonstop

9:52 pm - 12:58 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$199United Airlines

Thu, Oct 8 - Mon, Oct 12

1:10 pm - 2:26 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 16mnonstop

9:52 pm - 12:58 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$201United Airlines

Fri, Oct 16 - Mon, Oct 19

6:00 am - 1:50 pmPHL Philadelphia-ORD Chicago O'Hare Intl

8h 50m1 stop Fort Lauderdale

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

2h 23mnonstop

$204Multiple Airlines

Fri, Oct 30 - Mon, Nov 9

6:00 am - 1:44 pmPHL Philadelphia-ORD Chicago O'Hare Intl

8h 44m1 stop Fort Lauderdale

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

2h 16mnonstop

$204Multiple Airlines

Recent last minute flight deals from Pennsylvania to Chicago

Sun, Aug 30 - Sun, Sep 6

10:22 am - 11:55 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 33mnonstop

5:55 am - 9:04 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 09mnonstop

$207Frontier

Thu, Aug 27 - Sun, Nov 8

10:22 am - 11:55 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 33mnonstop

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

2h 16mnonstop

$224Frontier

Thu, Aug 27 - Mon, Sep 28

7:00 am - 8:46 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 46mnonstop

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

2h 27mnonstop

$257JetBlue

Wed, Aug 26 - Wed, Sep 30

3:40 pm - 5:35 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

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

2h 21mnonstop

$264JetBlue

Wed, Aug 26 - Wed, Sep 30

5:25 pm - 7:29 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

3h 04mnonstop

12:47 pm - 4:04 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 17mnonstop

$266American Airlines

Wed, Aug 26 - Mon, Sep 28

9:24 am - 11:12 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 48mnonstop

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

2h 11mnonstop

$266American Airlines

Wed, Aug 26 - Mon, Sep 28

6:00 am - 7:15 amLGA New York LaGuardia-MDW Chicago Midway

2h 15mnonstop

5:10 pm - 8:15 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$266Southwest

Wed, Aug 26 - Wed, Sep 30

9:35 pm - 10:50 pmLGA New York LaGuardia-MDW Chicago Midway

2h 15mnonstop

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

2h 00mnonstop

$266Southwest

Sat, Aug 29 - Wed, Sep 23

2:30 pm - 4:15 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 45mnonstop

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

2h 15mnonstop

$272Delta

Sat, Aug 29 - Mon, Sep 21

2:30 pm - 4:15 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 45mnonstop

6:00 am - 9:15 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$272Delta

Recent direct flight deals from Pennsylvania to Chicago

Sun, Sep 6 - Sun, Sep 6

10:22 am - 11:55 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 33mnonstop

8:30 pm - 11:53 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 23mnonstop

$168Frontier

Mon, Sep 14 - Fri, Sep 18

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

2h 36mnonstop

7:25 am - 10:49 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 24mnonstop

$168Frontier

Thu, Sep 24 - Mon, Sep 28

6:30 am - 7:58 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 28mnonstop

6:55 pm - 10:00 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$178American Airlines

Thu, Sep 17 - Mon, Sep 21

3:58 pm - 5:28 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 30mnonstop

8:55 pm - 11:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$178American Airlines

Mon, Sep 28 - Mon, Sep 28

8:20 am - 9:38 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 18mnonstop

9:52 pm - 12:58 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$199United Airlines

Thu, Oct 8 - Mon, Oct 12

1:10 pm - 2:26 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 16mnonstop

9:52 pm - 12:58 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$201United Airlines

Tue, Sep 8 - Tue, Sep 8

6:55 am - 8:42 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 47mnonstop

6:23 pm - 9:59 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 36mnonstop

$230JetBlue

Wed, Sep 16 - Sat, Sep 19

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

$237JetBlue

Tue, Sep 8 - Wed, Sep 16

7:35 am - 9:27 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

10:25 am - 1:49 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 24mnonstop

$242Delta

Tue, Sep 8 - Mon, Sep 14

7:35 am - 9:27 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

6:00 am - 9:21 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 21mnonstop

$242Delta

Useful Info

Low season	January
High season	October
Cheapest flight	$89

Best time to beat the crowds but there is an average 1% increase in price.

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

Flight from Reagan Washington National 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

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Munster

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Origins

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Return flight deals

Cabin class types available on flights to Pennsylvania

First Class flights to Chicagofrom $357

Business Class flights to Chicagofrom $497

Premium Economy Class flights to Chicagofrom $617

Economy Class flights to Chicagofrom $152

$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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Cheapest flight

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?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Pennsylvania

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

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight