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.

$90 CHEAP FLIGHTS from Pennsylvania to Chicago

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

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 12 - Mon, Nov 16

12:36 pm - 8:46 amPHL Philadelphia-ORD Chicago O'Hare Intl

21h 10m2 stops Atlanta Hartsfield-Jackson Orlando

6:00 am - 7:21 amORD Chicago O'Hare Intl-PHL Philadelphia

24h 21m2 stops Baltimore/Washington Atlanta Hartsfield-Jackson

$187Frontier

Fri, Feb 26 - Mon, Mar 1

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

$187Frontier

Fri, Feb 5 - Sun, Feb 7

5:25 am - 1:45 pmPHL Philadelphia-MDW Chicago Midway

9h 20m2 stops Nashville Intl Detroit Metropolitan Wayne County

7:50 am - 10:50 amMDW Chicago Midway-PHL Philadelphia

2h 00mnonstop

$188Southwest

Thu, Dec 10 - Sun, Dec 13

2:45 pm - 11:10 pmPHL Philadelphia-MDW Chicago Midway

9h 25m2 stops Lambert-St Louis Houston Hobby

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

1h 55mnonstop

$188Southwest

Tue, Dec 1 - Fri, Dec 11

6:00 am - 9:37 amPHL Philadelphia-ORD Chicago O'Hare Intl

4h 37m1 stop Washington, D.C. Dulles Intl

10:40 am - 1:55 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 15mnonstop

$190United Airlines

Fri, Dec 18 - Sun, Dec 20

12:22 pm - 6:26 pmPHL Philadelphia-ORD Chicago O'Hare Intl

7h 04m1 stop Detroit Metropolitan Wayne County

5:55 pm - 11:11 pmORD Chicago O'Hare Intl-PHL Philadelphia

4h 16m1 stop Detroit Metropolitan Wayne County

$193Delta

Fri, Feb 5 - Sun, Feb 7

12:09 pm - 6:32 pmPHL Philadelphia-ORD Chicago O'Hare Intl

7h 23m1 stop Atlanta Hartsfield-Jackson

5:45 pm - 11:02 pmORD Chicago O'Hare Intl-PHL Philadelphia

4h 17m1 stop Detroit Metropolitan Wayne County

$193Delta

Fri, Feb 26 - Mon, Mar 1

6:00 am - 11:41 amPHL Philadelphia-ORD Chicago O'Hare Intl

6h 41m1 stop Washington, D.C. Dulles Intl

6:25 pm - 9:38 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 13mnonstop

$198United Airlines

Sat, Dec 5 - Tue, Dec 8

10:30 am - 12:09 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 39mnonstop

5:00 pm - 8:14 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$199American Airlines

Wed, Feb 17 - Sat, Feb 20

10:01 pm - 11:30 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 29mnonstop

6:26 pm - 9:38 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 12mnonstop

$199American Airlines

Recent last minute flight deals from Pennsylvania to Chicago

Tue, Oct 27 - Fri, Nov 6

6:00 am - 7:08 pmPHL Philadelphia-ORD Chicago O'Hare Intl

14h 08m1 stop Dallas/Fort Worth

4:42 pm - 8:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 22mnonstop

$199Frontier

Sat, Oct 24 - Fri, Nov 6

6:00 am - 7:07 pmPHL Philadelphia-ORD Chicago O'Hare Intl

14h 07m1 stop Dallas/Fort Worth

4:42 pm - 8:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 22mnonstop

$217Frontier

Sat, Oct 24 - Tue, Nov 24

9:02 pm - 10:30 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 28mnonstop

6:29 am - 9:37 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 08mnonstop

$290American Airlines

Mon, Oct 26 - Sat, Nov 14

3:51 pm - 5:33 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 42mnonstop

7:29 pm - 10:53 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 24mnonstop

$334American Airlines

Sat, Oct 24 - Sat, Nov 7

10:15 am - 11:25 amPHL Philadelphia-MDW Chicago Midway

2h 10mnonstop

12:10 pm - 3:05 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$355Southwest

Sat, Oct 24 - Sat, Nov 7

11:40 am - 5:45 pmPHL Philadelphia-MDW Chicago Midway

7h 05m1 stop Lambert-St Louis

12:10 pm - 3:05 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$365Southwest

Tue, Oct 27 - Wed, Nov 4

12:36 pm - 6:45 pmPHL Philadelphia-ORD Chicago O'Hare Intl

7h 09m1 stop Atlanta Hartsfield-Jackson

12:15 pm - 9:30 amORD Chicago O'Hare Intl-PHL Philadelphia

20h 15m3 stops Quincy Regional Nashville Intl Orlando

$411Multiple Airlines

Mon, Oct 26 - Mon, Nov 2

6:30 am - 7:50 amMDT Harrisburg-ORD Chicago O'Hare Intl

2h 20mnonstop

6:55 am - 9:53 amORD Chicago O'Hare Intl-MDT Harrisburg

1h 58mnonstop

$414United Airlines

Sat, Oct 24 - Sat, Oct 24

6:08 am - 7:34 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 26mnonstop

6:15 pm - 9:29 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$415United Airlines

Tue, Oct 27 - Thu, Oct 29

12:36 pm - 6:45 pmPHL Philadelphia-ORD Chicago O'Hare Intl

7h 09m1 stop Atlanta Hartsfield-Jackson

12:30 pm - 8:20 pmORD Chicago O'Hare Intl-PHL Philadelphia

6h 50m2 stops Quincy Regional Nashville Intl

$449Multiple Airlines

Recent direct flight deals from Pennsylvania to Chicago

Mon, Nov 16 - Fri, Nov 20

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

2h 34mnonstop

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

2h 10mnonstop

$189Frontier

Thu, Nov 12 - Sun, Nov 15

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

2h 34mnonstop

4:42 pm - 8:04 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 22mnonstop

$189Frontier

Fri, Dec 11 - Sat, Jan 2

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

2h 39mnonstop

8:13 pm - 11:26 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 13mnonstop

$194Frontier

Fri, Feb 26 - Mon, Mar 1

11:15 am - 12:30 pmPHL Philadelphia-MDW Chicago Midway

2h 15mnonstop

2:50 pm - 5:40 pmMDW Chicago Midway-PHL Philadelphia

1h 50mnonstop

$197Southwest

Thu, Jan 14 - Sat, Jan 16

11:50 am - 1:00 pmPHL Philadelphia-MDW Chicago Midway

2h 10mnonstop

9:50 am - 12:45 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$198Southwest

Fri, Dec 11 - Tue, Dec 15

1:50 pm - 3:05 pmPHL Philadelphia-MDW Chicago Midway

2h 15mnonstop

11:25 am - 2:15 pmMDW Chicago Midway-PHL Philadelphia

1h 50mnonstop

$198Southwest

Sat, Dec 5 - Tue, Dec 8

10:30 am - 12:09 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 39mnonstop

5:00 pm - 8:14 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$199American Airlines

Wed, Feb 17 - Sat, Feb 20

10:01 pm - 11:30 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 29mnonstop

6:26 pm - 9:38 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 12mnonstop

$199American Airlines

Sat, Dec 5 - Sat, Dec 12

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

2h 36mnonstop

10:40 am - 1:54 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$199United Airlines

Tue, Dec 1 - Wed, Dec 2

9:45 am - 11:20 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 35mnonstop

9:00 am - 12:14 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$199United Airlines

Useful Info

Low season	February
High season	July
Cheapest flight	$90

Best time to beat the crowds with an average 9% drop in price.

Most popular time to fly with an average 5% increase in price.

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.

AdamFlew 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

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

More options for your flight to Chicago

Add a hotel or car rental

Cabin class

Direct Flights

Origins

Other airports

Other destinations

Return flight

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

Car rentals in Chicago

$90 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

Good to know

Low season

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?

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

Find direct flights for Chicago

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