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 19% 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.

Cheap Flights from Pennsylvania to Chicago

Cheap flights from Pennsylvania to Chicago with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Round-trip

One-way

Last minute

Direct

Wed, Nov 11 - Tue, Nov 17

12:36 pm - 5:47 pmPHL Philadelphia-MDW Chicago Midway

6h 11m1 stop Atlanta Hartsfield-Jackson

6:08 am - 6:19 pmMDW Chicago Midway-PHL Philadelphia

11h 11m1 stop Atlanta Hartsfield-Jackson

$184Frontier

Tue, Nov 10 - Fri, Nov 13

12:36 pm - 5:47 pmPHL Philadelphia-MDW Chicago Midway

6h 11m1 stop Atlanta Hartsfield-Jackson

6:42 pm - 7:21 amMDW Chicago Midway-PHL Philadelphia

11h 39m1 stop Atlanta Hartsfield-Jackson

$184Frontier

Wed, Oct 28 - Sat, Oct 31

7:45 am - 8:50 amPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

4:10 pm - 7:05 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$185Southwest

Thu, Dec 10 - Sat, Dec 12

6:20 pm - 7:35 pmPHL Philadelphia-MDW Chicago Midway

2h 15mnonstop

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

1h 55mnonstop

$185Southwest

Mon, Nov 9 - Wed, Nov 11

5:52 am - 7:27 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 35mnonstop

6:29 am - 9:39 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 10mnonstop

$185American Airlines

Thu, Dec 10 - Sat, Dec 12

9:16 am - 11:05 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 49mnonstop

3:19 pm - 6:30 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 11mnonstop

$185American Airlines

Mon, Nov 23 - Thu, Nov 26

6:15 am - 7:50 amPHL Philadelphia-ORD Chicago O'Hare Intl

2h 35mnonstop

11:03 am - 2:17 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 14mnonstop

$185United Airlines

Thu, Oct 29 - Sat, Oct 31

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

2h 35mnonstop

7:45 pm - 10:57 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 12mnonstop

$185United Airlines

Thu, Nov 12 - Mon, Nov 16

6:00 am - 9:46 amPHL Philadelphia-MDW Chicago Midway

4h 46m1 stop Detroit Metropolitan Wayne County

6:44 pm - 11:15 pmMDW Chicago Midway-PHL Philadelphia

3h 31m1 stop Detroit Metropolitan Wayne County

$205Delta

Thu, Nov 26 - Wed, Dec 2

6:00 am - 11:25 amPHL Philadelphia-MDW Chicago Midway

6h 25m1 stop Detroit Metropolitan Wayne County

6:00 am - 1:00 pmMDW Chicago Midway-PHL Philadelphia

6h 00m1 stop Atlanta Hartsfield-Jackson

$205Delta

Sat, Oct 17 - Fri, Oct 30

9:09 pm - 10:39 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 30mnonstop

4:42 pm - 7:58 pmORD Chicago O'Hare Intl-PHL Philadelphia

2h 16mnonstop

$187Frontier

Sat, Oct 17 - Sat, Oct 31

9:09 pm - 10:39 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 30mnonstop

7:15 am - 6:19 pmORD Chicago O'Hare Intl-PHL Philadelphia

10h 04m1 stop Atlanta Hartsfield-Jackson

$189Frontier

Thu, Oct 15 - Wed, Nov 4

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

2h 35mnonstop

9:11 pm - 12:19 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 08mnonstop

$334American Airlines

Thu, Oct 15 - Wed, Nov 4

3:20 pm - 4:25 pmPHL Philadelphia-MDW Chicago Midway

2h 05mnonstop

1:35 pm - 4:30 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$334Southwest

Thu, Oct 15 - Wed, Nov 4

2:35 pm - 8:20 pmPHL Philadelphia-MDW Chicago Midway

6h 45m1 stop Orlando

1:35 pm - 4:30 pmMDW Chicago Midway-PHL Philadelphia

1h 55mnonstop

$344Southwest

Sun, Oct 18 - Sun, Oct 25

8:07 am - 9:10 amERI Erie-ORD Chicago O'Hare Intl

2h 03mnonstop

9:10 pm - 11:55 pmORD Chicago O'Hare Intl-ERI Erie

1h 45mnonstop

$349American Airlines

Sat, Oct 17 - Sat, Oct 31

6:15 am - 7:41 amAVP Wilkes-Barre Scranton-ORD Chicago O'Hare Intl

2h 26mnonstop

5:50 pm - 8:57 pmORD Chicago O'Hare Intl-AVP Wilkes-Barre Scranton

2h 07mnonstop

$369United Airlines

Wed, Oct 14 - Sun, Nov 1

1:24 pm - 2:50 pmPHL Philadelphia-ORD Chicago O'Hare Intl

2h 26mnonstop

6:35 am - 9:45 amORD Chicago O'Hare Intl-PHL Philadelphia

2h 10mnonstop

$383United Airlines

Sun, Oct 18 - Sat, Oct 31

6:10 am - 10:29 amPHL Philadelphia-ORD Chicago O'Hare Intl

5h 19m1 stop Detroit Metropolitan Wayne County

5:27 am - 12:53 pmORD Chicago O'Hare Intl-PHL Philadelphia

6h 26m1 stop Atlanta Hartsfield-Jackson

$399Delta

Sat, Oct 17 - Sat, Oct 17

9:48 am - 12:59 pmPHL Philadelphia-ORD Chicago O'Hare Intl

4h 11m1 stop Detroit Metropolitan Wayne County

5:42 pm - 11:08 pmORD Chicago O'Hare Intl-PHL Philadelphia

4h 26m1 stop Detroit Metropolitan Wayne County

$415Delta

Low season	February
High season	July
Cheapest flight	$90

Best time to beat the crowds with an average 12% 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.