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

Fri, Jan 29 - Sun, Jan 31

12:46 pm - 2:19 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 33mnonstop

5:32 pm - 12:28 amORD Chicago O'Hare Intl-PHL Philadelphia

5h 56m1 stop Atlanta Hartsfield-Jackson

$177Frontier

Fri, Jan 22 - Sun, Jan 24

12:46 pm - 2:19 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 33mnonstop

5:32 pm - 12:28 amORD Chicago O'Hare Intl-PHL Philadelphia

5h 56m1 stop Atlanta Hartsfield-Jackson

$177Frontier

Wed, Dec 2 - Sat, Dec 5

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

2h 39mnonstop

5:47 pm - 9:00 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 13mnonstop

$257American Airlines

Sat, Oct 10 - Sat, Oct 17

5:33 pm - 7:20 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 47mnonstop

6:29 am - 9:40 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 11mnonstop

$257American Airlines

Wed, Dec 16 - Thu, Dec 17

10:53 am - 12:29 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

2:35 pm - 5:44 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 09mnonstop

$257United Airlines

Mon, Nov 9 - Tue, Nov 10

4:59 pm - 6:34 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 35mnonstop

6:42 am - 9:52 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 10mnonstop

$257United Airlines

Thu, Nov 5 - Mon, Nov 9

11:40 am - 12:50 pmPHL Philadelphia-MDW Chicago Midway

2h 10mnonstop

7:25 pm - 10:20 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$257Southwest

Mon, Oct 26 - Wed, Oct 28

11:30 am - 12:35 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

6:00 pm - 9:05 pmMDW Chicago Midway-PHL Philadelphia

2h 05mnonstop

$257Southwest

Fri, Dec 11 - Thu, Dec 17

6:50 pm - 8:29 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 39mnonstop

11:45 am - 11:20 amORD Chicago O'Hare Intl-PHL Philadelphia

22h 35m1 stop Minneapolis St Paul

$267Multiple Airlines

Fri, Dec 11 - Thu, Dec 17

6:50 pm - 8:29 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 39mnonstop

11:45 am - 11:20 amORD Chicago O'Hare Intl-PHL Philadelphia

22h 35m1 stop Minneapolis St Paul

$277Multiple Airlines

Recent last minute flight deals from Pennsylvania to Chicago

Thu, Sep 24 - Sat, Oct 10

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

$219Frontier

Fri, Sep 25 - Tue, Oct 27

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

2h 36mnonstop

7:50 pm - 7:21 amORD Chicago O'Hare Intl-PHL Philadelphia

10h 31m1 stop Atlanta Hartsfield-Jackson

$228Frontier

Sat, Sep 26 - Tue, Oct 27

7:39 pm - 9:30 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 51mnonstop

4:50 pm - 8:10 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 20mnonstop

$326American Airlines

Sat, Sep 26 - Tue, Oct 27

7:30 pm - 11:31 pmPHL Philadelphia-ORD Chicago O'Hare Intl

5h 01m1 stop Washington, D.C. Dulles Intl

6:26 pm - 9:40 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$336United Airlines

Sat, Sep 26 - Tue, Oct 27

3:40 pm - 4:45 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

7:45 am - 10:40 amMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$343Southwest

Tue, Sep 29 - Sat, Oct 10

3:54 pm - 8:56 pmPHL Philadelphia-ORD Chicago O'Hare Intl

6h 02m1 stop Atlanta Hartsfield-Jackson

6:08 pm - 12:56 amORD Chicago O'Hare Intl-PHL Philadelphia

5h 48m1 stop Atlanta Hartsfield-Jackson

$346Delta

Sat, Sep 26 - Sat, Oct 10

8:50 am - 2:29 pmPHL Philadelphia-ORD Chicago O'Hare Intl

6h 39m1 stop Atlanta Hartsfield-Jackson

5:29 pm - 11:08 pmORD Chicago O'Hare Intl-PHL Philadelphia

4h 39m1 stop Detroit Metropolitan Wayne County

$346Delta

Sat, Sep 26 - Tue, Oct 27

3:40 pm - 4:45 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

4:30 pm - 9:50 pmMDW Chicago Midway-PHL Philadelphia

4h 20m1 stop Lambert-St Louis

$353Southwest

Fri, Sep 25 - Tue, Oct 27

10:20 pm - 11:56 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

8:29 am - 11:42 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 13mnonstop

$370American Airlines

Sun, Sep 27 - Tue, Oct 27

6:10 am - 7:35 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 25mnonstop

2:35 pm - 5:47 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 12mnonstop

$370United Airlines

Recent direct flight deals from Pennsylvania to Chicago

Fri, Nov 20 - Mon, Nov 23

6:31 pm - 8:15 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 44mnonstop

9:20 pm - 12:30 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 10mnonstop

$178Frontier

Mon, Dec 21 - Mon, Dec 28

4:56 pm - 6:40 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 44mnonstop

7:45 pm - 11:00 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 15mnonstop

$179Frontier

Fri, Nov 20 - Mon, Nov 23

6:31 pm - 8:15 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 44mnonstop

9:20 pm - 12:30 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 10mnonstop

$179Frontier

Wed, Dec 2 - Sat, Dec 5

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

2h 39mnonstop

5:47 pm - 9:00 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 13mnonstop

$257American Airlines

Sat, Oct 10 - Sat, Oct 17

5:33 pm - 7:20 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 47mnonstop

6:29 am - 9:40 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 11mnonstop

$257American Airlines

Mon, Nov 9 - Tue, Nov 10

4:59 pm - 6:34 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 35mnonstop

6:42 am - 9:52 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 10mnonstop

$257United Airlines

Wed, Dec 16 - Thu, Dec 17

10:53 am - 12:29 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 36mnonstop

2:35 pm - 5:44 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 09mnonstop

$257United Airlines

Thu, Nov 5 - Mon, Nov 9

11:40 am - 12:50 pmPHL Philadelphia-MDW Chicago Midway

2h 10mnonstop

7:25 pm - 10:20 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$257Southwest

Mon, Oct 26 - Wed, Oct 28

11:30 am - 12:35 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

6:00 pm - 9:05 pmMDW Chicago Midway-PHL Philadelphia

2h 05mnonstop

$257Southwest

Tue, Oct 20 - Wed, Oct 21

7:25 am - 9:00 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 35mnonstop

4:50 pm - 8:10 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 20mnonstop

$257American Airlines

Useful Info

Low season	February
High season	October
Cheapest flight	$91

Best time to beat the crowds with an average 10% drop in price.

Most popular time to fly and prices are also 6% lower on average.

Flight from Philadelphia 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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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