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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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

Mon, Sep 21 - Thu, Sep 24

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

$166Frontier

Thu, Nov 12 - Sun, Nov 15

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

Wed, Oct 21 - Thu, Oct 22

3:47 pm - 5:05 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 18mnonstop

8:50 am - 11:55 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 05mnonstop

$177United Airlines

Wed, Sep 23 - Thu, Sep 24

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

2h 14mnonstop

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

2h 06mnonstop

$177United Airlines

Mon, Oct 5 - Thu, Oct 8

8:35 pm - 10:00 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 25mnonstop

6:59 am - 10:06 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 07mnonstop

$177American Airlines

Mon, Feb 1 - Mon, Feb 1

6:00 am - 7:27 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 27mnonstop

4:50 pm - 7:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 09mnonstop

$177American Airlines

Tue, Sep 22 - Wed, Sep 23

11:10 am - 4:59 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

6h 49m1 stop New York John F Kennedy Intl

5:10 pm - 11:02 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

4h 52m1 stop Detroit Metropolitan Wayne County

$194Delta

Sat, Sep 19 - Mon, Sep 21

12:18 pm - 4:14 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

4h 56m1 stop Detroit Metropolitan Wayne County

5:10 pm - 11:14 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

5h 04m1 stop Detroit Metropolitan Wayne County

$197Delta

Mon, Oct 5 - Wed, Oct 7

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

2h 36mnonstop

7:11 am - 11:18 pmORD Chicago O'Hare Intl-PHL Philadelphia

15h 07m3 stops Fort Lauderdale Tampa Atlanta Hartsfield-Jackson

$206Multiple Airlines

Mon, Sep 28 - Wed, Sep 30

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

2h 36mnonstop

7:11 am - 11:18 pmORD Chicago O'Hare Intl-PHL Philadelphia

15h 07m3 stops Fort Lauderdale Tampa Atlanta Hartsfield-Jackson

$206Multiple Airlines

Recent last minute flight deals from Pennsylvania to Chicago

Sat, Sep 5 - Thu, Sep 10

2:45 pm - 8:08 pmPHL Philadelphia-ORD Chicago O'Hare Intl

6h 23m1 stop Atlanta Hartsfield-Jackson

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

2h 24mnonstop

$193Frontier

Sat, Sep 5 - Thu, Sep 10

4:45 pm - 7:53 amPHL Philadelphia-ORD Chicago O'Hare Intl

16h 08m1 stop Atlanta Hartsfield-Jackson

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

2h 24mnonstop

$197Frontier

Sat, Sep 5 - Mon, Sep 21

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

2h 58mnonstop

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

2h 27mnonstop

$277JetBlue

Sat, Sep 5 - Sat, Sep 26

2:30 pm - 4:18 pmJFK 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

Sat, Sep 5 - Mon, Sep 21

1:00 pm - 8:08 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

8h 08m1 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

Sat, Sep 5 - Sat, Sep 26

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

2h 46mnonstop

10:11 am - 1:30 pmORD Chicago O'Hare Intl-EWR Newark

2h 19mnonstop

$286American Airlines

Sat, Sep 5 - Wed, Sep 30

5:19 pm - 7:20 pmEWR Newark-ORD Chicago O'Hare Intl

3h 01mnonstop

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

2h 21mnonstop

$286American Airlines

Sat, Sep 5 - Mon, Sep 21

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

2h 47mnonstop

5:00 am - 8:14 amORD Chicago O'Hare Intl-EWR Newark

2h 14mnonstop

$286United Airlines

Wed, Sep 2 - Sat, Sep 26

8:29 pm - 10:15 pmEWR Newark-ORD Chicago O'Hare Intl

2h 46mnonstop

5:00 am - 8:12 amORD Chicago O'Hare Intl-EWR Newark

2h 12mnonstop

$286United Airlines

Sat, Sep 5 - Sat, Oct 3

1:00 pm - 8:08 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

8h 08m1 stop Atlanta Hartsfield-Jackson

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

2h 21mnonstop

$293Multiple Airlines

Recent direct flight deals from Pennsylvania to Chicago

Mon, Sep 21 - Thu, Sep 24

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

$166Frontier

Thu, Nov 12 - Sun, Nov 15

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

Mon, Oct 5 - Thu, Oct 8

8:35 pm - 10:00 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 25mnonstop

6:59 am - 10:06 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 07mnonstop

$177American Airlines

Mon, Feb 1 - Mon, Feb 1

6:00 am - 7:27 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 27mnonstop

4:50 pm - 7:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 09mnonstop

$177American Airlines

Sat, Nov 7 - Mon, Nov 9

6:06 pm - 7:30 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 24mnonstop

12:29 pm - 3:37 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 08mnonstop

$177United Airlines

Wed, Oct 28 - Thu, Oct 29

7:40 am - 9:00 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 20mnonstop

7:00 am - 9:56 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 56mnonstop

$177United Airlines

Sun, Oct 4 - Thu, Oct 8

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

2h 48mnonstop

12:38 pm - 4:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 22mnonstop

$230JetBlue

Sat, Oct 3 - Mon, Oct 5

3:01 pm - 5:03 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

$239Delta

Wed, Sep 30 - Fri, Oct 2

3:01 pm - 4:59 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

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

2h 21mnonstop

$239Delta

Sat, Sep 19 - Sun, Sep 20

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

$248JetBlue

Useful Info

Low season	February
High season	October
Cheapest flight	$89

Best time to beat the crowds with an average 8% drop 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

Hammond

Saint Joseph

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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Complete your trip

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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 $357

Business Class flights to Chicagofrom $583

Premium Economy Class flights to Chicagofrom $661

Economy Class flights to Chicagofrom $165

$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