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 - Tue, Nov 10

11:05 am - 12:41 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

6:30 am - 1:12 pmORD Chicago O'Hare Intl-PHL Philadelphia

5h 42m1 stop Atlanta Hartsfield-Jackson

$166Frontier

Thu, Oct 29 - Fri, Oct 30

11:05 am - 12:41 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

6:00 am - 2:25 pmORD Chicago O'Hare Intl-PHL Philadelphia

7h 25m1 stop Dallas/Fort Worth

$166Frontier

Tue, Sep 15 - Sat, Sep 26

9:04 pm - 11:51 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

15h 47m1 stop Atlanta Hartsfield-Jackson

7:11 am - 6:33 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

10h 22m2 stops Fort Lauderdale Tampa

$194Multiple Airlines

Mon, Aug 31 - Thu, Sep 3

6:40 pm - 12:50 pmPHL Philadelphia-ORD Chicago O'Hare Intl

43h 10m2 stops Tampa Fort Lauderdale

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

2h 23mnonstop

$196Multiple Airlines

Sat, Sep 5 - Sat, Sep 12

5:47 pm - 10:36 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 49m1 stop Atlanta Hartsfield-Jackson

5:37 pm - 11:14 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

4h 37m1 stop Detroit Metropolitan Wayne County

$197Delta

Wed, Oct 21 - Sat, Oct 24

6:00 am - 10:03 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 03m1 stop Atlanta Hartsfield-Jackson

6:44 pm - 11:16 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

3h 32m1 stop Detroit Metropolitan Wayne County

$197Delta

Tue, Sep 29 - Fri, Oct 30

2:05 pm - 3:21 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 16mnonstop

10:39 am - 4:28 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

4h 49m1 stop Newark

$197United Airlines

Sat, Sep 12 - Sat, Sep 19

8:40 am - 10:10 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 30mnonstop

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

2h 05mnonstop

$197American Airlines

Thu, Oct 15 - Mon, Oct 19

7:45 am - 9:11 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

5:59 am - 9:14 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 15mnonstop

$197American Airlines

Sat, Oct 10 - Mon, Oct 12

10:18 pm - 11:31 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 13mnonstop

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

2h 06mnonstop

$198United Airlines

Recent last minute flight deals from Pennsylvania to Chicago

Fri, Aug 21 - Sat, Oct 24

6:00 am - 7:29 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 29mnonstop

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

2h 23mnonstop

$172Frontier

Thu, Aug 20 - Thu, Sep 3

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

$189Frontier

Sun, Aug 23 - Thu, Sep 17

10:29 pm - 7:53 amEWR Newark-ORD Chicago O'Hare Intl

10h 24m1 stop Atlanta Hartsfield-Jackson

3:00 pm - 11:06 pmORD Chicago O'Hare Intl-EWR Newark

7h 06m1 stop Fort Lauderdale

$257Multiple Airlines

Sat, Aug 22 - Tue, Sep 1

6:50 am - 8:36 amEWR Newark-ORD Chicago O'Hare Intl

2h 46mnonstop

6:43 am - 10:02 amORD Chicago O'Hare Intl-EWR Newark

2h 19mnonstop

$262American Airlines

Sat, Aug 22 - Tue, Sep 1

5:29 am - 7:15 amEWR Newark-ORD Chicago O'Hare Intl

2h 46mnonstop

6:43 am - 10:02 amORD Chicago O'Hare Intl-EWR Newark

2h 19mnonstop

$262American Airlines

Sat, Aug 22 - Sat, Sep 19

9:45 pm - 11:22 pmEWR Newark-ORD Chicago O'Hare Intl

2h 37mnonstop

2:32 pm - 6:01 pmORD Chicago O'Hare Intl-EWR Newark

2h 29mnonstop

$267United Airlines

Sat, Aug 22 - Tue, Sep 1

5:55 pm - 7:57 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

3h 02mnonstop

5:40 pm - 9:07 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 27mnonstop

$267Delta

Sat, Aug 22 - Tue, Sep 1

7:35 pm - 9:52 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 17mnonstop

6:00 am - 9:24 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 24mnonstop

$267Delta

Thu, Aug 20 - Wed, Nov 25

1:35 pm - 8:15 pmEWR Newark-ORD Chicago O'Hare Intl

7h 40m1 stop Dallas/Fort Worth

3:20 pm - 11:55 pmORD Chicago O'Hare Intl-EWR Newark

7h 35m1 stop Fort Lauderdale

$276Multiple Airlines

Sat, Aug 22 - Tue, Aug 25

6:20 pm - 8:07 pmEWR Newark-ORD Chicago O'Hare Intl

2h 47mnonstop

8:40 am - 11:58 amORD Chicago O'Hare Intl-EWR Newark

2h 18mnonstop

$287United Airlines

Recent direct flight deals from Pennsylvania to Chicago

Fri, Oct 30 - Sun, Nov 1

11:05 am - 12:41 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

6:50 am - 10:00 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 10mnonstop

$167Frontier

Thu, Oct 8 - Sat, Oct 10

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

$168Frontier

Sat, Sep 12 - Sat, Sep 19

8:40 am - 10:10 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 30mnonstop

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

2h 05mnonstop

$197American Airlines

Thu, Oct 15 - Mon, Oct 19

7:45 am - 9:11 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

5:59 am - 9:14 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 15mnonstop

$197American Airlines

Sat, Oct 10 - Mon, Oct 12

10:18 pm - 11:31 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 13mnonstop

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

2h 06mnonstop

$198United Airlines

Thu, Oct 8 - Mon, Oct 12

6:10 am - 7:25 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 15mnonstop

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

2h 06mnonstop

$200United Airlines

Fri, Sep 11 - Sun, Sep 13

7:35 pm - 9:37 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

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

2h 21mnonstop

$214JetBlue

Tue, Sep 1 - Wed, Sep 2

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

2h 55mnonstop

6:30 pm - 10:06 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 36mnonstop

$228JetBlue

Wed, Sep 2 - Wed, Sep 2

7:25 am - 8:45 amLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

12:25 pm - 3:30 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$237Southwest

Tue, Sep 1 - Wed, Sep 2

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

2h 15mnonstop

9:30 am - 12:35 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$237Southwest

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

Chesterton

Munster

Schererville

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 $564

Business Class flights to Chicagofrom $497

Premium Economy Class flights to Chicagofrom $617

Economy Class flights to Chicagofrom $130

$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

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