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

Tue, Oct 27 - Thu, Oct 29

12:43 pm - 7:44 pmPHL Philadelphia-ORD Chicago O'Hare Intl

8h 01m1 stop Atlanta Hartsfield-Jackson

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

2h 10mnonstop

$174Frontier

Thu, Sep 24 - Mon, Oct 5

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

2h 36mnonstop

6:00 am - 2:21 pmORD Chicago O'Hare Intl-PHL Philadelphia

7h 21m1 stop Dallas/Fort Worth

$174Frontier

Sun, Oct 4 - Wed, Oct 7

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

2h 36mnonstop

7:11 am - 7:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

10h 53m2 stops Fort Lauderdale Tampa

$185Multiple Airlines

Mon, Sep 7 - Wed, Sep 9

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

2h 29mnonstop

7:11 am - 7:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

10h 53m2 stops Fort Lauderdale Tampa

$187Multiple Airlines

Sun, Sep 6 - Sun, Sep 6

10:45 am - 1:55 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

4h 10m1 stop Cleveland Hopkins Intl

5:55 pm - 8:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$192American Airlines

Sat, Sep 5 - Fri, Sep 11

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

5h 49m1 stop Atlanta Hartsfield-Jackson

5:03 pm - 11:14 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

5h 11m1 stop Detroit Metropolitan Wayne County

$197Delta

Sun, Sep 6 - Fri, Sep 11

6:10 am - 9:17 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

4h 07m1 stop Detroit Metropolitan Wayne County

4:30 pm - 12:41 amMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

7h 11m1 stop Atlanta Hartsfield-Jackson

$197Delta

Sat, Sep 5 - Sat, Sep 5

3:59 pm - 5:57 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 58mnonstop

8:25 pm - 11:45 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 20mnonstop

$212American Airlines

Fri, Sep 11 - Tue, Sep 15

3:15 pm - 4:29 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 14mnonstop

10:50 am - 1:55 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 05mnonstop

$216United Airlines

Wed, Sep 2 - Sat, Sep 5

10:27 pm - 11:40 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 13mnonstop

2:30 pm - 5:37 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 07mnonstop

$216United Airlines

Recent last minute flight deals from Pennsylvania to Chicago

Thu, Aug 13 - Sat, Aug 15

6:05 pm - 7:47 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 42mnonstop

8:52 pm - 12:15 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 23mnonstop

$213Frontier

Wed, Aug 12 - Wed, Aug 26

5:00 pm - 7:12 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

3h 12mnonstop

6:00 am - 9:09 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 09mnonstop

$216Delta

Wed, Aug 12 - Wed, Aug 26

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

$216Delta

Wed, Aug 12 - Wed, Sep 2

10:29 pm - 8:02 amEWR Newark-ORD Chicago O'Hare Intl

10h 33m1 stop Atlanta Hartsfield-Jackson

1:59 pm - 9:28 pmORD Chicago O'Hare Intl-EWR Newark

6h 29m1 stop Atlanta Hartsfield-Jackson

$217Frontier

Thu, Aug 13 - Fri, Sep 11

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

2h 46mnonstop

8:38 pm - 11:59 pmORD Chicago O'Hare Intl-EWR Newark

2h 21mnonstop

$257American Airlines

Tue, Aug 11 - Tue, Aug 11

8:27 am - 10:30 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 03mnonstop

4:30 pm - 8:01 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 31mnonstop

$257American Airlines

Wed, Aug 12 - Wed, Aug 19

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

2h 15mnonstop

5:45 pm - 8:55 pmMDW Chicago Midway-LGA New York LaGuardia

2h 10mnonstop

$257Southwest

Thu, Aug 13 - Mon, Aug 17

8:00 pm - 9:58 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

6:00 am - 9:17 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 17mnonstop

$265JetBlue

Thu, Aug 13 - Tue, Aug 18

6:55 am - 8:43 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

6:00 am - 9:17 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 17mnonstop

$265JetBlue

Tue, Aug 11 - Tue, Aug 11

6:30 am - 11:50 amLGA New York LaGuardia-MDW Chicago Midway

6h 20m1 stop Lambert-St Louis

7:05 pm - 10:10 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$267Southwest

Recent direct flight deals from Pennsylvania to Chicago

Thu, Aug 27 - Sun, Aug 30

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

2h 33mnonstop

6:00 am - 9:17 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 17mnonstop

$175Frontier

Thu, Aug 27 - Sun, Aug 30

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

2h 33mnonstop

6:00 am - 9:17 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 17mnonstop

$175Frontier

Sat, Sep 5 - Sat, Sep 5

3:59 pm - 5:57 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 58mnonstop

8:25 pm - 11:45 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 20mnonstop

$212American Airlines

Thu, Sep 10 - Fri, Sep 11

2:54 pm - 4:18 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 24mnonstop

9:53 am - 12:58 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$216American Airlines

Fri, Sep 11 - Tue, Sep 15

3:15 pm - 4:29 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 14mnonstop

10:50 am - 1:55 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 05mnonstop

$216United Airlines

Wed, Sep 2 - Sat, Sep 5

10:27 pm - 11:40 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 13mnonstop

2:30 pm - 5:37 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 07mnonstop

$216United Airlines

Tue, Aug 25 - Tue, Sep 1

10:55 am - 12:15 pmLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

7:05 pm - 10:10 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$217Southwest

Wed, Sep 2 - Sat, Sep 5

8:00 pm - 9:58 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

5:27 pm - 9:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 33mnonstop

$217JetBlue

Wed, Sep 2 - Sat, Sep 5

8:00 pm - 9:58 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

5:27 pm - 9:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 33mnonstop

$217JetBlue

Wed, Aug 26 - Sat, Aug 29

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

2h 15mnonstop

6:00 am - 9:00 amMDW Chicago Midway-LGA New York LaGuardia

2h 00mnonstop

$222Southwest

Useful Info

Low season	January
High season	October
Cheapest flight	$89

Best time to beat the crowds but there is an average 2% 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

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Pennsylvania

First Class flights to Chicagofrom $553

Business Class flights to Chicagofrom $497

Premium Economy Class flights to Chicagofrom $396

Economy Class flights to Chicagofrom $132

$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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High season

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